Old Town Through Rose-Colored Glasses … Looking Back at Wells Street

1967 Tourism Poster

North and Wells 1960

The Meter Maid: The late Judy Marco, April 11, 1966 (Credit: Judy Marco)

Wells Street Street by Art Shay 1970

Lately I have been thinking about how much I adored North Wells Street in Chicago’s Old Town in my youth. My parents took us to Old Town on occasion and every single trip was imbued with magic. I’m not alone in this adoration – in my research I found quite a few blogs devoted to this unique street. Of course Old Town is far more than Wells St. – it consists of the charming, tree-lined residential and historic district defined by the triangle formed by North Avenue, Clark Street, and Ogden Avenue. Commercial Old Town is the busy stretch of North Wells running from Division Street roughly north to Lincoln Avenue and a small piece of North Ave., east and west. To residents in the 1960s to 70s, North Wells was a fabricated medley of oddities targeted at suburbanites and tourists looking for an edgy, artsy thrill in the big city. This June 7, 1964 Chicago Tribune article certainly implies North Wells was a Disneyfied tourist attraction.

“It’s far from the true Bohemian atmosphere the tourists think they are savoring, but North Wells street is fascinating, lively, colorful, crowded and a pot of gold for the merchants. Like any night-life addict, Old Town’s Wells street sleeps until just before noon when it opens one reluctant eye to welcome the day’s first visitors: the suburban matrons. Sleek and well-dressed, they motor in from the north shore or the far western suburbs to infiltrate the shops and restaurants. ‘They arrive at 11:30,’ says Kris Perkins, co-proprietor of Charlie’s General Store, citing their movements as precisely as an almanac predicts the orbits of the heavenly bodies. ‘They eat lunch until 12:30, then shop until 3 O’clock when they all leave at once to beat the traffic and get home before their husbands.'”

Regardless of this cynical view, as an artistic child, I really dug the Wells Street vibe and aura and certainly didn’t know any better. When I was 12, I asked my mom to take me there and it was just the two of us – a very special birthday outing, indeed. To me, it was magically mysterious and a far cry from downtown Skokie, Lincoln Village Shopping Center, Old Orchard, or Rogers Park – the places where my family shopped. The book Our Old Town, The History of a Neighborhood, mentions 80 Old Town Ale House regulars chartering a bus to suburbia to turn the tables on the suburbanites “ruining” their neighborhood tavern. They descended on the lawn of a Mrs. Callahan in Lincolnwood and asked for beer – yes, Lincolnwood – the place I grew up and blogged about so fondly in three separate recent articles! After this stop, they spread out and asked other Lincolnwood residents for beer. I wonder if they visited the Lincolnwood Towers, a place city dwellers descend upon every Christmas season to gaze at the decorations. The very next weekend, more suburbanites than ever descended on Old Town, including Mrs. Callahan – their little social experiment failed miserably, despite media coverage!

Crate and Barrel


Original Crate and Barrel

Old Town Crate and Barrel 1960s

Photo Credit: Algimantas Kezys

Before it was a 170+ store American chain of retail stores, Crate and Barrel was a one-of-a-kind shop at 1510 N. Wells. Gordon and Carole Segal opened the first Crate and Barrel store on December 7, 1962 at the ripe old age of 23. The couple raised $17,000 to launch their business, $7,000 of which was used to convert part of an old elevator factory into a 1,700 sq. ft. retail space. They could not afford new plaster for the walls and fixtures, so they nailed crating lumber on the walls.  French pottery, Swedish glass, and Danish flatware spilled out of wooden packing crates, while other chic, yet moderately priced European goods were stacked on top of upside down barrels. I clearly remember shopping here with my parents and at the Crate and Barrel store at Plaza Del Lago in Wilmette, which opened in 1968.

Piper’s Alley


Pipers Alley by Robert Birkenes

Pipers Alley Model Shoot

Pipers Alley Poster

Many people loved Piper’s Alley, including me. A quaint, cobblestone passageway, Rudolph Schwartz and Jack Solomon opened Piper’s Alley in November 1965. The alley consisted of five buildings that once housed Piper’s Bakery and stables, with an odd array of as many as 15 businesses. A giant Tiffany lamp hung outside the entrance to the maze of eclectic shops. Patrons of Piper’s Alley could buy candles, party goods, decorator items, handicrafts, jewelry, records, posters, candy, ice cream, new and vintage clothing, delicious pizza, and head shop merchandise. Charlie’s General Store, owned by Kris Perkins, was the first store shoppers would encounter upon entering the alley. The place looked like a disaster zone, with merchandise strewn all over the place, crocks full of back scratchers, and shelves piled high with frying pans, however, this state of disarray was intentional.

Pipers Alley Scene

Charlies General Store 1970

Next to Charlie’s was Penelope’s Premises, a 1903-style ice cream parlor selling ice cream sodas for 95 cents, the “$1.00 Integration, A Blending of Vanilla, Chocolate, and Marshmallow Without Incident” and everything else including tables, chairs, faux antiques and even a brass bed. Back in 1890, the ground floor of this establishment was a horse stable. In December 1964, this business simply became Penelope’s, a classy cocktail lounge with black-tie waitstaff serving New Orleans style seafood. According to this Chicago Tribune review dated December 13, 1964:

“Decor remains turn-of-the-century vintage, but with suave changes keynoted now by a collector’s array of old stained and leaded glass chandeliers. The second floor dining room is a cheerful and gay looking place with bright red table cloths and an occasional leaded glass window, one of them in what formerly was a skylight. Our dinner there recently was off to a tasty start with shrimps de Jonghe, and from there to a crisp green salad and a delicious broiled fresh red snapper. Someone ordered chicken Vesuvio, and we tried a savory piece of that. The ingenious designer, Warren Black, also was decorator for That Steak Joynt, one of Old Town’s most successful cafes, located at 1610 N. Wells across the alley from Penelope’s.”

Pipers Alley

That Steak Joynt 1610 N Wells

That Steak Joynt

Several restaurants were housed in or adjacent to this complex, including La Piazza Restaurant, which apparently had incredibly delicious pizza. The most famous restaurant was That Steak Joynt owned by Billy Siegel, just north of the alley. The restaurant was purported to be haunted, tied to two unsolved murders around the turn of the 19th century in which both victims were found in Piper’s Alley. Siegel speculated the ghosts of the murder victims had decided to “set up house” in his establishment. Aside from the ghosts, patrons loved dining on delicious steaks and burgers amid red velvet walls and near decadent Victorian furnishings. Among the most spectacular relics were an original bakery display case from Piper’s Bakery, a white marble statue of a smiling peasant with a wine flask, and a 600-pound Second Empire Viennese mirror from the Thorne Estate.

Aardvark in Pipers Alley

Photo Credit: Pete Lekousis, 1973

Pipers Alley Fire 1971

On March 1, 1971, a fire gutted the loft above the Aardvark Cinematheque in Piper’s Alley. Smoke damage to other businesses was minor and the merchants were able to rebound fairly quickly. The Aardvark was an art movie theater that opened originally some time in 1966 in The Second City building at 1843 N. Wells. In July 1967, likely  in response to The Second City relocating, Aardvark moved to Piper’s Alley and was able to expand to 240 seats. The movie house showed avant-garde and experimental films including Andy Warhol’s Flesh.

A graphic in the March 12, 1971 Chicago Tribune article about the Piper’s Alley fire mentions Design India, but I thought the shop was called India Imports. Either my memory is inaccurate or in 1968, it was called India Imports and the name was subsequently changed. I believe there was another location in downtown Skokie. This cool store was owned by the father of my fourth grade friend Jody Dutt (sp?). I remember Jody bringing some inexpensive jeweled tin rings to class and giving me one – the little gemstones were genuine, but just garnets and citrine. They sold wonderful printed textiles, scarves, jewelry, and many other imported goods, long before Devon Avenue became a haven for East Indian goods.

Chances R


Chances R 1970

Chances R 1963

Chances R Promo

Although That Steak Joynt was not my family’s style, I have fond memories of eating at several other restaurants on Wells Street. One of our family favorites was Chances R at 1528 N. Wells, which opened in 1961. They had delicious char-broiled hamburgers and of course, we loved the free bowls of peanuts and throwing the shells all over the floor. The owners decorated the interiors with a mélange of antiques and oddities found at local thrift and antique stores. The restaurant’s name reportedly came from Richard Baldwin, one of the owners. When they opened the Old Town location it was a rundown neighborhood, so Baldwin remarked, “chances are we could go broke.” Instead it was a huge hit and Chances R locations were added in Hyde Park, River Oaks, Skokie, Palatine, Champaign and Boyne City, Michigan.

Chances R REO Speedwagon

The Wells Street location became a mainstay hangout during the hippie days of the 1960s. The Champaign location was a popular music venue and stomping ground for University of Illinois students. Acts such as REO Speedwagon, Cheap Trick, and a young, unknown Bruce Springsteen performed there. Dig those prices on the above poster! Sadly, the owners lost their lease and the original location on Wells closed its doors in May 1969. By the late 1970s, most of the remaining Chances R locations succumbed to competition, changing neighborhoods, and financial problems. The last holdout was the Hyde Park location, which closed in 1983.

The Pickle Barrel


The Pickle Barrel

Leo Oshler established The Pickle Barrel at 1423 N. Wells. The menu featured deli sandwiches and non-Jewish deli fare like ribs, fried shrimp, and Sloppy Joes. Balloon artists entertained the kids, while adults enjoyed pitchers of beer. The walls were decorated with oddities, antiques, and memorabilia, and the tables and chairs didn’t match, a creative, uncommon touch at that time. Guests were greeted with a barrel of pickles and popcorn on the tables to snack on while waiting for their meals to arrive. According to Osher’s obituary in the Chicago Tribune, in an average week the restaurant would go through 10 barrels of pickles and 400 pounds of popcorn. Oshler opened four additional Pickle Barrels including one on Oak Street and another one in the Howard and Western Shopping Center. I remember the latter location was a favorite of my childhood friend Myra and her family. Osher sold the Pickle Barrel chain in the late 1970s. Oshler and his son Michael opened Barnum & Bagel in Skokie, which they briefly considered calling “20th Century Lox.” It closed in 2006 and the deteriorating building was demolished.

The Cave & The Bowl and Roll


The Cave Wells Street

I remember eating at The Cave with my family and thought it was the coolest restaurant I had ever eaten at. The seats were tree trunks covered in deer or cowhide fur and I think the tables were rustic looking free-form stone-like slabs. The walls looked like something out of The Flintstones with faux cave paintings. I wanted to cut off a piece of the fur or bring the entire stool home! Marsh and Michi Kobata and grandma ran the Cave. The Cave served sashimi/do it yourself sushi tempura and warm sake, long before this became popular in America.

The Bowl and Roll was run by Chef Louie Szathmary and his wife Sada, owners of the famous Bakery Restaurant on Lincoln Avenue. Sada was the sister of the owner of the Cave. After grandma was no longer cooking at the Cave, Bowl and Roll moved over to the same spot as the Cave and changed out some of the decor. A November 1974 article in the Chicago Tribune raves about the delicious soup and choice of three sandwiches, but complained about the noise level. It also mentions the cave-like atmosphere and primitive paintings on the walls and ceiling. However, the description of paper doilies on wooden tables and silverware wrapped in paper napkins sounds a lot more mundane than The Cave.



No article on Wells Street is complete without mentioning The Second City, which opened at 1843 N. Wells on a snowy night in 1959, the Earl of Old Town, which opened at 1615 N. Wells in 1962, and the Old Town School of Folk Music, founded in 1957 at a run-down storefront at 333 W. North.

The Second City

So many stars got their start at The Second City – among them Paul Sills, Alan Arkin, Barbara Harris, Robert Klein, David Steinberg, Fred Willard, John Belushi, Dan Aykroyd, Gilda Radner, Tina Fey, Mike Myers, Steve Carell, and Stephen Colbert. Although I never went to The Second City, I certainly enjoyed the many comedians who learned their craft at this humorously hallowed institution. It has been at its current location at 1616 N. Wells since 1967.

Earl of Old Town with Taxi

The Earl of Old Town Cafe & Pub became synonymous with the burgeoning Chicago folk scene, with home-grown talent including Steve Goodman, John Prine, and Bonnie Koloc. During the first few years, it was a bar and burger joint, featuring jazz and classical music from a record player. In 1964, Earl J.J. Pionke bought his partners out and by 1966, other folk clubs such as the Montmartre, Gate of Horn, and Mother Blues had closed, so Pionke introduced live music to the venue. Fred Holstein, a young fixture on the folk scene, began performing at the club regularly and helped attract crowds and other performers. The club soon became one of the most well-known and popular clubs in Chicago, and arguably the most famous folk music venue in the country, until its doors closed in 1984.

I have a personal connection to the Old Town School of Folk Music. When I got married to my first husband in June 1981, we hired folk singer Jim Hirsch to perform at the reception. Hirsch served as executive director of the Old Town School of Folk Music from 1982 to 2000 and is credited with transforming it into a financially-sound, thriving institution. Unfortunately, the poor guy barely had a chance to sing at my wedding – my dad was so wound up he kept grabbing the mike away and took over as a stand-up comedian.

The Old Town Art Fair


Old Town Art Fair 1960 by Marguerite Baker-Johnson

Browsing at Old Town Art Fair - June 3, 1950

This June marks the 69th Old Town Art Fair, rated number one in America and one of Chicago’s favorite festivals. I never attended this fair, but I know my parents bought work here in the 1950s to early 1960s and several of their artist friends exhibited at this iconic fair. A few years ago, they gave me a piece they bought there – it hung on the wall outside my childhood bedroom and I always admired it.

Eclectic Shops


Paper Lantern Lampshade

Beyond the excellent eateries, it is the cool stores of my youth that infuse my memories of Wells Street with a rose-colored hue. I cannot find any information about this store called That Paper Place – we also shopped at a location on the southeast corner of Dempster and Crawford in Skokie. I know I am not imagining this because my mom confirmed we shopped there. They sold giant paper flowers, all sorts of decorations, cards, and the paper lantern-style lampshade fixtures my older sister was so fond of – in fact, the one in her childhood bedroom (similar to above) was purchased there. Alas, no blogs on North Wells or Skokie mention this cool store, so it is lost to history. I did find this intriguing photo of The Fig Leaf Paper Dress Shop, although I have no recollection of ever shopping there.

Fig Leaf and Paper Dress Store

The Emporium

Twirl O' Paint

I clearly remember my parents letting me shop at an incredible store loaded with racks of cool jewelry, pinback buttons, and other eclectic merchandise. It may have been The Emporium, but since I could not locate any descriptions of this shop, I’m not positive. In any case, one night after dining at Chances R, I bought a genuine whale tooth on a rawhide lace and a pinback button I kept all these years. I clearly remember having problems selecting something from the spin rack chock full of necklaces – so many glorious choices and just $1.00 each! I wore the whale tooth necklace everywhere I went the summer of ’70 and remember leaving it in the back yard of a family friend’s house in Winnetka. I was so distressed, I made my dad drive there the next day to retrieve it. The whale tooth pictured below is similar to the piece I cherished. My parents also gave each of us  $1.00 to create twirl paintings – I recall this may have been offered at The Fudge Pot or at an adjacent store. Basically, this was similar to the Ohio Art Twirl O’ Paint toy, but larger. Primary colored paint splattered randomly on a piece of cardboard placed in the center of this spinning device – thrilling, right?

Oriental Gift Shop TopTown and the Fudge Pot 1971
Uno's Bizarre Bazaar

Bizarre Bazaar

Childhood Treats

As already mentioned, my mom took me to Old Town for my 12th birthday. We went to several stores including The Oriental Gift Shop where my mom bought me three dolls – one was a Japanese girl doll sitting on a red cushion and the others were inexpensive little Chinese finger puppets (similar to the ones pictured above). Of course, we had to stop at The Fudge Pot to satisfy my sweet tooth. It is reassuring to know this candy shop is still thriving after more than 50 years – one of a handful of businesses from my youth still going strong. We wandered into Uno’s Bizarre Bazaar where I recall all sorts of head shop merchandise such as pipes, bongs, strawberry flavored rolling papers, black light posters, love beads, etc. Needless to say, this was not exactly our style, but the place is indelibly etched in my memory. By 1991, it had become a flea market of sorts with t-shirts, posters, hats, clothing, sunglasses and other eclectic paraphernalia. It has long disappeared and expensive condos were built at the approximate address.

Up Down Cigar Shop

No mention of Old Town is complete without mentioning UP Down Cigar shop. Diana Silvious Git opened the Gerald Bernard Art Gallery at 205 W. North in 1963 with her husband Gerald. The gallery sold work by local artists, a variety of quirky merchandise, and tobacco products. The art was downstairs and the cigars and tobacco products were upstairs, thereby inspiring the unusual name. By 1965, the business was booming, so Git expanded her operation and the tobacco section of the shop was given a fair share of space. The store moved around the corner into a three-flat apartment building at the corner of Burton and Wells the same year. Up Down Cigar shop moved to its present location at 1550 N. Wells in 1976. Git died in January 2016 at the age of 81 – she was known as the Titan of Tobacco – quite a title for a male-dominated industry!



The Bijou

Bijou Poster

Old Town was home to many gays and lesbians from the 1960s through the 1980s, before Boystown fully blossomed. Of course I had no idea about the existence of these businesses until much later – like the mid-1980s. Glory Hole (1342 N. Wells), Our Den (1355 N. Wells), and Willoughby’s (1608 N. Wells) were three gay bars listed in a 1974 Chicago Gay Bar directory. I worked at a north suburban telecommunications company from 1985 to 1991, and one of the accounts was an unassuming gay video business on Wells – it was a mail order catalog, not a retail business. I remember the macho technicians saying homophobic things about it and bringing a catalog back to the office. The Bijou Theater at 1349 N. Wells held out for a long time and earned the distinction of the longest running gay theater in the U.S. before closing its doors on September 30, 2015.

Tourist Traps


Wax Museum and Ripley's

My parents never would have considered taking us to The Royal London Wax Museum at 1419 N. Wells or Ripley’s Believe it or Not! at 1500 N. Wells. I’m pretty certain they thought these places were a waste of money and too touristy, and I was none the wiser. The Royal London Wax Museum included wax figures of Chicagoans Ernie Banks, Hugh Hefner, and Al Capone and more generic figures like Dracula, Frankenstein, Cinderella and Alice in Wonderland. The wax museum also featured horrific scenes including Bonnie and Clyde’s death and the St. Valentine’s Day Massacre.

Ripley’s, which opened in 1968,  featured a 90-year-old mummified orange, a record-breaking hairball, and Weng the Human Unicorn, among other treasures. By 1987, the 7,250-square-foot, bi-level museum building was being offered for $649,000. According to the Canadian owners, the two primary factors were an increasing demand for commercial property in the area and a dramatic shortage of shrunken heads!

Wells Street – Here and Now

Old Town Today

The Wells Street of today is a far cry from the magical street of my youth. It could be any other shopping area in a gentrified neighborhood with several cookie-cutter franchises including McDonald’s, Starbucks,  Einstein Bros Bagels, and Sports Clips. At least a few businesses from the glory days are still around: The Second City, Old Town Aquarium, Old Town Ale House, The Fudge Pot, and Up Down Cigar – and of course, the Old Town Art Fair is going strong. I find it reassuring some things have survived the vagaries of time and progress.

Photo sources: Calumet 412, Cinema Treasures, Craigs Lost Chicago, drloihjournal.blogspot.com, ebay, Fine Art America, Old Town Triangle Association, Pinterest,  YouTube


  1. A couple of places I remember from childhood visits to my favorite neighborhood of Old Town include the House of Horrors Wax Museum (yes, a tourist trap) and Lums Restaurant where I would order Sloppy Joe. There was also a strip club called The Crystal Pistol. They kept the front door open so we could look inside at topless dancing women as we passed. I also remember candle stores. I loved reading this blog entry.

    • Thanks for reading the blog and sharing your memories. I was looking for photos of strip clubs in Old Town, but couldn’t locate any, other than a very poor example of a go-go bar. Now that I have a name, I will do some further sleuthing. I’m glad you enjoyed the read!

      • Jim D'Agostino

        Other strip clubs on Wells were the Midas Touch (near the Crystal Pistol) and The Bowery (same side of street, farther south). I don’t have photos.

    • Glad to hear there are a few folks with memories of the Crystal Pistol. It was my grandparent’s place. I remember being a very young kid running around there, must have been the early seventies – being fussed over by the dancers, playing with the resident Great Dane, and having my grandmother take me to various places mentioned in this blog post.

  2. Stefanie Newman

    Oh yes – Chances R. First restaurant I ever heard of where you threw your peanut shells on the floor. And the penny candy place…first time I ate Swedish Fish. People really went to Old Town to gawk at hippies. It was such a different time. I remember going to a large family gathering and my mother warning me in advance that my cousin had a…Beard! She didn’t want me to stare.

  3. Carlise Ballinger

    This brought back so many memories. I must admit hearing about the suburbanites was funny and a little surprising. My friends and family spent a lot of time in Old Town and we all lived in the city proper. I celebrated my graduation from high school at Three Brother’s Pizza. It was my absolute favorite pizza. I live in Las Vegas now and visit home every few years. I have tried to find that pizza place and find no mention of it anywhere. Seeing this article gave me hope, but now I am just confused. I am wondering if my memory is flawed. Let me also say how sad I was to see Old Town become just another place, little about it seems special anymore.

    • Hi Carlise: Glad this article brought back memories and thanks for sharing some of yours. Perhaps one of the readers of this blog remembers Three Brother’s Pizza and will post something. You’re right – Wells Street in Old Town is just like any other somewhat upscale shopping street in Chicago, although residents would definitely say the architecture and history are unique.

      • Nick Cosentino

        That’s what the name of the pizza place was…3 Brothers! Thanks. I have always asked people if they remembered the great Pizzeria at the end of Pipers Alley but I always called it just “Brothers. I remember they also had a deep dish very similar to Uno’s and better than Gino’s East. BTW, there was also another great pizzeria called Dino’s Grotto. Not in Old Town but near it and closer to Rush Street. I think it may have been on Chestnut and off of Wabash and down a flight of stairs below street level and it had heavy stucco walls that made it look like a cave. Great Deep Dish! I think it was owned by a guy named Joe who always told me that Gino’s East was family and they stole his recipe. I’m not sure if that was true or if it might have been the other way around. But in the Grotto, the seating was wooden tables and bench like seats and both had thousands of carvings on them of peoples initials or names and dates. Kind of like the graffiti in markers at Gino’s now. I think Joe finally moved and opened another place right on Rush and Oak by the ballsy name of Gino’s West (or maybe it was just Gino’s) with the same MO (Wooden tables with marker graffiti all over the place). That pizza wasn’t as good as his original or even as good as Gino’s East (I’m an Uno’s fan anyway and yes, there is a difference)!


          I sure remember the Grotto! I was in high school in 1965 and went to Old Town with friends. The pizza was AMAZING! I recall it was made in heavy cast iron pans, and served hot straight from the oven. So glad you posted this! I had forgotten the name of the restaurant, but it’s always been a great memory. Thank you!

  4. Hi – My fond memories of The Cave (that I frequented almost daily between ’64-’70) and The Bowl and Roll are a bit different. Both were family-owned businesses. The Cave served Japanese food and The Bowl and Roll, soup with a roll … nothing else. Restaurants were across the street from each other. Marsh and Michi along with grandma ran the Cave … Bowl and Roll was run by Chef Louie Szathmary and his wife Sada, also owners of the famous Bakery Restaurant on Lincoln Avenue.

    The Cave served sashimi/do it yourself sushi tempura and warm sake – all exciting and exotic at that time. Love your blog. Brought back great memories!

    • Hi Nancy – thanks for sharing your memories and glad you enjoyed it. I stand by what I wrote – The Cave and The Bowl and Roll were both at 1339 N. Wells, based on the pictured matchbook and Chicago Tribune article I referenced: http://archives.chicagotribune.com/1974/11/29/page/51/article/where-the-soup-will-bowl-you-over/ Here is an excerpt: The Bowl and Roll, 1339 N. Wells St., has a cave atmosphere with imitation primitive drawings on the walls and ceiling. Paper doilies are used on the wooden tables and the silverware is wrapped in paper napkins.

      • Carole Toigo-

        Nancy is right – Bowl and Roll was across the street. Later when grandma was no longer cooking at the Cave, Bowl and Roll moved over to the Cave. Chef Szathmary’s wife Sada was the sister of the owner of the Cave. They changed the decor after it became Bowl and Roll.

  5. A couple more clarifications:

    The Meter Maid pictured on North Avenue is the late Judy Marco. The photo is from April 11, 1966 and should be credited to her.
    It is looking West on North Avenue, with the Plaza Theatre blade sign in the background. The Plaza was located at 308 W. North Avenue.

    The photo of the girl seated out front of the Aardvark Cinematheque should be credited to Pete Lekousis, 1973. That was his girlfriend at the time.

    • Thank you for the clarifications – added appropriate captions and removed the incorrect photo!

      • Update: The B&W Earl Of Old Town photo with the Coca Cola van is “May 1977 photo credit Guy Arnston.”
        It was a photo used on the cover of the Illinois Entertainer.


    Spent many a Saturday there in the early seventies. I equate my experiences there to the scene in the Wizard of Oz movie where Dorothy opens the door and the movie switches from black and white to color…Chicago’s own Disneyland!!!

  7. I miss our real Old Town!! Thanks so much for the memories! ✌

  8. Don’t Forget Moody’s Pub, Pickle Barrel plus the Old Old Town Pump.

    • Pickle Barrel is included in the blog … but thanks for mentioning Moody’s Pub and the Old Town Pump. Moody’s Pub opened in Old Town in 1959, moving to Larrabee St when rents started escalating. After a 1969 fire destroyed that location, it moved to 5910 N. Broadway.

  9. The photo of Crate and Barrel from across Wells was taken by Algimantas Kezys. The woman whose back we see in the pic is his long-time companion, Donna. Both are deceased, but the photo credit is his.

    • Thank you, Tony – I greatly appreciate this information and added the appropriate photo credit to this photo.

  10. I really enjoyed this walk down Wells. As a teenager from the NW suburbs, we would steal in to Chicago and wander around taking it all in. I remember the pizza place in Piper’s Alley that I recall had really great pizza, but we also found a peep hole in the women’s bathroom – lol. Very fond memories. Thank You!

    • Hi Diane: So glad you enjoyed the trip down memory lane and thanks for sharing your memories. The peep hole in the bathroom is very creepy … in this day and age, the perpetrator would likely be busted due to technology.

    • That was great pizza! The Man at Ease and the candy store where the Cryan’ Shames had their album cover shot for the first LP (inside). ~ Dale

  11. Whitney C Brown

    My mother, Peggy Cartwright (then Saperston), published and produced most of The Old Town Guide Book which sold for 25 and 50 cents depending on the year and edition. I have no idea if she ever made any real money on it except for advertisements for which I doubt she charged much either – the ads were also mostly designed and written by her. I still have a good amount of the editions of that great book. I trip down memory lane with her stories and the general layout of each guide. Peggy is still very much alive, at 93, and living in San Franciso, where she left her heart when I was about 5 years old.

  12. Whitney C Brown

    I failed to mention she owned two shops – Tea for Two (a popular place for English tea and sandwiches and great ice cream next to Adele’s) and a china shop in the same location – the name of it escapes me. Movie stars visiting Old Town used to stop by and eat at Tea for Two. Very popular place but again, she didn’t take into account the overhead for very generous portions of food and ice cream. I grew up in Old Town on Eugenie St and Lincoln Park West. My mother was a Bohemian artist who did enamel and silver and copper jewelry – also a painter and puppet maker.

    • Hi Whitney – Thank so much for your two comments and great memories. I especially love hearing from people who have very personal connections to a place. Your mom sounds like a wonderful and very interesting person. It must have been quite an experience growing up in Old Town. If you have any vintage photos of your mother’s Old Town businesses or artwork, I would love to see both! As an artist and longtime antique collector myself, this greatly intrigues me. Even a digital photo of the Old Town Guide Book cover would be great – I could add it or any other photos you wish to share to the blog!

  13. Dale G. Niewoehner

    As a student in Chicago in the late 1960’s I often visited OLD TOWN. I remember the CAVE – good to know that others did also. The t-shirt shops, candle stores, poster stores, and stores selling incense were very interesting. It is nice to remember these better times than we have today.

  14. Dale G. Niewoehner

    Oh, I forgot – The Old Town Art Fair. I still have the piece of art that I purchased at the Fair in the 1960’s…and Chances R. I used to frequent the “branch” in Hyde Park with peanuts on the floor and big mugs of cold beer. I recall seeing Bob Dylan in “Don’t Look Back” at the Aardvark theater – and then there was the Tap Root Pub. These are great memories of a gentle time in the big city. Listening to Norm and Ray on the Midnight Special on WMFT.

  15. I remember going to the wax museum in Old Town as a child. There were two ticket windows. One was operational and the other had a wax figure of an older man in front of it. People would routinely wait in line behind him until they realized he wasn’t moving.

    Also remember a shop that had shadow box picture frames of rooms with mouse figures. I adored them, but they weren’t for sale. I loved looking at them and would stop to see them every time my family ventured to Old Town.

  16. For several years I lived in an apartment that overlooked Gaslight Court, where the exit for the Wax Museum was and worked at Can-It – a little shop in the courtyard. At the exit was a man dressed in a werewolf costume who stood in an exhibit and if the crowd was not moving along fast enough he would let out a fierce “Grooowl” and send screaming customers flying out the door. The little diner next door, the Cow Palace, was staffed with many newly arrived Greek immigrants who spoke little or no English. It looked just like the set from the Belushi SNL skit “Cheeps, no fries” and I was told once that the place was his inspiration. But people who seemed to know more about it jumped all over me, saying I was wrong.

    • Yes, we used to sneak in the back door you mentioned at the Wax Museum. When people came out, we would grab the door and go in. Would walk through most of it, but not the front where we would be seen. Harmless enough – we never did anything malicious, just walked through and out the back door. A lot of fun in Old Town back in the day.

  17. Who were the owners of Chances R? My cousin attended U of I and he and his partners owned a couple bars in Champaign and Chicago. My husband shopped at a clothing store in Old Town … hippy colorful slacks and shirts. The shop was touted as a place Joe Cocker frequented. Names of clothing shops?

    • Thanks for writing, Mary. Richard (“Dick”) Baldwin was the founder and owner of the Chances R chain. He was the son of a Swift meatpacking company executive. Baldwin said he and two of his bachelor buddies entered the restaurant business as a hobby. Uno`s Bizarre Bazaar was quite famous and sold T-shirts, posters, hats, clothing, sunglasses, and other eclectic paraphernalia.

    • House of Lewis, perhaps.

      • Constance J Fletcher

        I worked the front counter at House of Lewis in either 1968 or 1969. It was a blast. Lewis had his Mom and Dad working in the store with him.

  18. Does anyone remember the name of the toy store that was across from Treasure Island, just down from Piper’s Alley? My best childhood friend and I cannot remember the name and it’s killing us!

    • It was the Toy Gallery! It was great. Eventually it moved to the lower north corner inside the Americana Building. It is fun reading this site and the shared comments. I grew up on Willow St. We would walk every Friday to Azteca on North Avenue. Eventually Piper’s Alley had a Baskin Robbins 31 Flavors – it must have been where the Bratskeller was…

  19. Barbara’s Bookstore?

  20. My father owned Jamie’s on the corner of Burton and Wells – it was a strip club. Next door was the cat lady – she sold cats. Ripley’s was across the street. My dad bought his pipe tobacco at Up Down Cigar shop – those were the good days of Old Town.

  21. Thanks for the memories. I remember Chances R, the Plugged Nickel, and the Outhaus of the 1969s together with the jazz and all the pretty ladies. “Oh what a time it was!” All I can hope for now is eternal recurrence of the same.

  22. I am 61 this year. My sister used to take us down to Old Town when I was young. I want to say ’67 or ’68. I remember it pretty well – Pipers Alley. Went to the Wax Museum and Ripley’s. I have fond memories of it, but because I was young, I only remember the things a kid would recall. A little note here … our best friends and neighbors were Morris and Gail Barazani. Mr. Barazani founded the art department at DePaul University. He and Gail also were founding members who created the Old Town Art Fair. Wonderful article. Thank you.

  23. This great article brought back so many memories. I was a suburban kid but my friends and I (particularly after one of my friends got his driver’s license) often hung out in Old Town.

    I definitely remember the great pizza and I still have the autographs of John Sebastian and Joe Butler of the Lovin’ Spoonful who I met while shopping at a strange clothing store (I don’t remember the name). I bought a Sgt. Pepper-style coat and while I was there, Sebastian and Butler came in. They were not happy to be recognized but grudgingly signed their names for me.

    Old Town and Piper’s Alley were terrific. I am sorry but not surprised to learn it has been redeveloped and gentrified. That’s life.

    • Hi Joel: I’m glad you enjoyed this blog. I am wondering if you still have the Sgt. Pepper-style jacket? That is quite a story about meeting John Sebastian and Joe Butler. There were so many cool and strange stores in Old Town back then. You’re right – nothing stays the same. Just found out yesterday Hollywood Mirror on Belmont is closing – one of the few stores in Chicago that just might have a vintage Sgt. Pepper jacket!

      • Yes, your post brought back many memories – not all of them great (there were some rip-off artists roaming the streets), but all of them special.

        I do not have the jacket anymore – I always suspected my mother threw it out when I went off to college. But the store must have been pretty cool to attract the likes of the Lovin’ Spoonful.

    • Dale K, Hallebach

      I might have been the man at ease in Pipers Alley. Being from the western burbs – I bought cool hip clothes there. The candy store is where the Cry’n Shames were photographed for their first LP … Sugar and Spice.

    • My husband bought his wedding suit at the Man at Ease and I bought him an orange and blue silk scarf to tie around his neck. The store was down the street from Piper’s Alley and had very stylish and wild men’s clothes.

  24. Great article and fantastic photos! Thank you. I was a Chicago kid who went to NIU in ’67. For the first two years I’d take the Greyhound back to the city to see my girlfriend and hang out with friends. My friends and I would always head to Old Town. Psychedelic, man! There was a head shop on Wells – I think on the west side of Wells. It was very narrow – like a gangway between two buildings. Can’t remember the name but if anyone does, please post. They sold posters, incense, and albums. It was my meek step into the rabbit hole of hippy culture.

    • Hi Rich:

      Glad I helped you take a trip down psychedelic memory lane and thanks for posting! Uno’s Bizarre Bazaar was a head shop with pipes, bongs, strawberry flavored rolling papers, black light posters, love beads, etc. on the east side of the street. I remember it as a multi-vendor flea market of sorts. It wasn’t especially narrow, so there must have been another head shop before my time.

  25. Loved the Bowl and Roll. Miss their chicken soup. My father took me there twice a year.

  26. Larry Van Nevel

    I remember The Man At Ease, a clothing store at 1706 N. Wells St. I would cut classes in high school to shop for hip clothing (MOD styles and European clothing) there. The first album of Chicago’s Cryan’ Shames band credits MAE for supplying the clothing worn on album cover, as well as the House of Lewis and Zepher (I bought my elephant bell bottoms there). I also saw Chicago folk artists John Prine, Fred Holstein, Steve Goodman, Bonnie Kolack, and Jim Post at the Earl of Old Town. Also remember Crate & Barrel’s first store.

  27. I loved reading your blog. I was a city kid – Logan Square in my early years. North and Central as a teen. My friends and I would go to the Lake, day and night. I couldn’t remember the name of the restaurant with the red velvet chairs. Thank you, it was the Steak Joynt. I so miss the old Old Town. I would buy my old ripped jeans at a shop in Piper’s Alley. One year when I was about 16, I saw someone wearing a ripped mink coat in Old Town. That was it, asked gram if I could have hers. So many good times with good friends. Favorite place to eat was the Pickle Barrel. Bazaar Bazaar, head shops, record stores! Thank you!

    • Hi Carol – So pleased you enjoyed the blog and it brought back such fond memories. Thanks for sharing your personal experiences in Old Town!

    • Could the store you bought your jeans at have been Second Hand Rose? I seem to remember going there to buy jeans. At least I think it was called that. Does anyone remember Second Hand Rose?

  28. Not yet mentioned: The Leather Fetish on Wells Street, where I worked after school in 1966-67 (owner was Karl Liss). John Brown’s leather shop in Piper’s Alley. Beans And, a tiny diner in an alley off Wells Street.

    • Did you know Stephen and Roberta Custer? They had a leather shop on Wells and used to make clothes for George Hamilton. They were good friends…lost touch when I moved to Tucson in ’72.

  29. Thanks for this – great photos and history. MGM released a movie called “The Young Runaways” in 1968 and it includes a fair amount of footage filmed in the Old Town area. TCM shows it once in a while.

    • Thanks, Eric – This looks like an interesting B-movie with a motley group of actors. Richard Dreyfuss (early in his career), Dick Sargent (second Darrin in Bewitched), Norman Fell (Three’s Company), and Isabel Sanford (The Jeffersons). The lead actress Brooke Bundy hasn’t acted since 1991 and the lead actor Kevin Coughlin died in a car accident in 1976 at the age of 30. I would like to see this movie just for the scenes of Old Town.

      • I was 15, a runaway from Michigan, it was the summer of ‘67. I lived in a 3rd story apt on Webster, 2-3 blocks north of Wells. In addition to myself there was Paul, Linda, “Sloopy”, and one or two others. I frequently would walk Wells. I loved Pipers Alley. There was a men’s clothing store on Wells named U.S. Male that always had great men’s clothing – suits on mannequins in the front windows. I remember spending a day at a “B-in” in Lincoln Park. I remember there were one or two places with names like the “Hungry Eye” or “Purple Onion”. I’m not sure of the names now. As a 15-year-old, they seemed cool and exotic. I loved Old Town. The short time I lived there for 5-6 weeks changed my life. Mostly for the better! – Larry

        • Hi Larry – What an incredible personal connection you have to Old Town. I’m glad you weren’t living on the street, survived this time, and it changed your life mostly for the better!

  30. What about Lums? I remember eating at Lums where the hot dogs were steamed in beer and you could buy pitchers of cheap beer. My friends and I would always stop for refreshments.

  31. The Be-In is on YouTube.

    There is a great Facebook group called Chicago Old Town in the 1960’s, link below.
    I added photo of LUM’S a while back if you do a Group search.


  32. There were also a bunch of small boutiques and head shops along Wells. The Smuggler and Chinese restaurant China Doll, as well as a Mexican restaurant.

    Thank you so much for the memories!


    My uncle Robert (Bob) Turk was one of the original owners of Chances R. My folks would go there on a Saturday night and tell us kids about the strange people they encountered. I do not know how long his relationship with the business lasted.

  34. My dad and his brothers owned a business on Wells – James J. Mullally and Sons – don’t remember the address. I remember going there on Saturdays with my dad to clean the office and eat at The Cave.

  35. Sandra R Johanson

    Thank you for this walk down memory lane! I have many happy memories of this place from 1965-70. My family loved the charbroiled burgers at Chances R – I can almost taste them as I think of them! I wandered the streets with my HS boyfriend in 1969 and bought some cool and funky earrings that I still have – maybe from The Emporium!

  36. What was the name of the restaurant in Piper’s Alley that served the best hamburgers on rye bread and hot German potato salad? Also, does anyone remember something called the Chicago Free Theatre? Whatever it was called, it was on the east side of Wells a few blocks down from North. Music acts would play and if memory serves me, it was painted black inside. I swear I saw CTA perform there one night!!!

    • The restaurant with the great burgers and German Potato Salad was possibly Ratskellar or Bratskellar. It was next to the Steak Joynt, I think in the basement.

  37. How about The Plugged Nickel? Great jazz heard there with the likes of Wes Montgomery, Miles Davis, Cal Tjader, Jimmy Smith, Kenny Burrell & others.

    • The restaurant with the great burgers and German Potato Salad was possibly Ratskellar or Bratskellar. It was next to the Steak Joynt, I think in the basement.

  38. You’ve done a great job on this. I was hanging out in Old Town in the 60s and early 70s, particularly at the music clubs. But as a boy, I remember my mother taking me for waffles at the restaurant on the corner of North and Wells. Do you remember the name?

  39. Stage Coach Restaurant was on the S/E corner, LUM’S was on the S/W corner.

    • I worked at One Octave Lower (Maiden Lane) and The Flypped Disc (Piper’s Alley) in the later 60’s. Owned by Stu and Noel Gimbel. That’s where I developed my love of all types of music and where Janis Joplin wrote a birthday card for my boyfriend. Great memories!!

      Does anyone remember the name of the bookstore in Piper’s Alley?

  40. John J Mackey

    Does anyone remember the clothing boutique on the west side of Wells just north of Schiller?

    • There was Man at Ease and Horse of a Different Color. South of North Ave was Gallimaufry and Male M1 in Maiden Lane. Any of those what you were looking for?

  41. Thanks for all that. My apartment was upstairs from Sibyl’s Art Gallery, right between Chances R and the Crystal Pistol where there were always go-go girls dancing behind a curtain in the front window. It was 1971-1972. Being young and stupid, my lifestyle was rather nocturnal at times. Many a morning, I’d find myself sitting on the front steps and waiting for Nelson Algren to walk by, as he always did at just about 6 am. I was 22 and he was somber and scary looking with the most unapproachable vibe I have ever experienced. I couldn’t even squeak out the faintest “Good morning, Mr. Algren.” Several years later, I read in Time Magazine that he had moved to Paterson, New Jersey stating that Chicago was no longer ugly enough for him.

    • Correction: It was the Midas Touch, not the Chrystal Pistol that had go-go girls behind the window curtain. There…I feel better now.

      • No wait! I think it was the Chrystal Pistol…not The Midas Touch…damn! Can someone help me out?

  42. Laurence Braude

    Surprised at no mention of the legendary Big John’s, 1638 N. Wells. Google this link for a terrific description:

    BLUES FOR BIG JOHN’S by George Spink

  43. I remember the area and shops well from my childhood. Our family went there sometimes after going to the Fullerton Ave beach (beach #3 was our favorite). I still have a few knick-knacks in a box in the basement from those shops and the exact same Japanese doll pictured in your blog! One time, we had to stop to go to the bathroom and we went into a bar. The bathrooms were downstairs, which also housed a strip joint. While my mom went to the bathroom (she probably didn’t realize what it was), someone outside in the hallway picked me up so I could look through the high window, and I saw a stripper dancing. My mother would have been horrified but I was fascinated. I remember it vividly. Also remember paper dresses, smiley face everything, paper flowers, peace signs, bottles of colorful water, bead curtains… good times! Thanks for illustrating my memories so vividly!

    • Hi Olivia – Thanks for sharing your vivid memories and glad you enjoyed this blog. I wish my mom used the bathroom at that strip club – I would have been as fascinated as you! Instead, she made a pit stop at the Belden-Stratford Hotel in Lincoln Park before heading to Old Town! It sure would be wonderful to turn the clock back.

  44. Dale Hallebach

    I bought hip clothes there myself…quality and cool! I love the memories of Piper’s Alley.

  45. I used to go to Wells Street when I was 15-years-old just to hang out. I’m 68 now, soon to turn 69, so that tells you how long ago it was that I experienced Wells Street. Along with just hanging out, I used to go to the The Man at Ease. In addition to buying clothes, I’d beg the owners Johan or Cesar for a job. I loved the feeling of that clothing store. I lied about my age and got a job at restaurant on the street named Little Pleasures. The owner was a really nice person to let me work there. Eventually, I worked at House of Louis with my best friend Peter James Nordloh, but would always continue to beg the two owners of Man at Ease for a job.

    At one point I lived above Piper’s Alley. One of the pictures posted in this blog shows the bay window of the apartment I lived in. In this picture, the bay windows are painted blue. I sublet, (that’s what it’s called these days) back when it was simply word-of-mouth. Someone told me they were moving back to New York and asked me if I wanted to rent the room. It was perfect, except unbeknownst to me the people I was living with were serious drug dealers. Not like I didn’t do drugs but I wasn’t aware of drugs to that extent.

    One night there was a knock on the door and before anybody could open it, off came the hinges and six Chicago police officers broke it down. I had hair down to the middle of my back at the time. They separated everyone and went through the apartment, literally tearing it apart. I remember they brought me into my room and said, Oh, is he a girl or a boy. Real funny, ha, ha, ha! I had a guitar and they picked it up and said, I wonder if there are drugs in this guitar and smashed it against the wall. I won’t go on with this story, except to say they found no drugs because as I later find out, my roommates were smart enough to stash all their drugs behind the baseboard in the kitchen.

    Moving on…when I worked at House of Louis, I met Grace Slick and Led Zeppelin – all really nice people. And then one day when I was at the Electric Theater, I saw Cesar the owner of The Man at Ease and I begged him again to give me a job and this time he said yes. Unfortunately, The Man at Ease had moved or maybe they had a second store on Clark Street and that was where I was employed. The feeling of this store was not at all the same as the one on Wells Street. At just 16, I still feel like I had arrived and was a big shot. I have many stories about Wells Street. To this day, living on that street was probably the best time of my life and I’ve had a very good life. If anyone’s interested about my experience at La Pizzeria, just ask.

  46. David Lightner

    I lived in Chicago 1967-1970 and visited Piper’s Alley many, many times. I remember most of the establishments mentioned here. I believe the bookstore (which somebody has said was called Barbara’s) was owned by the woman who also ran the famous Oak Street Bookshop. I ate at the The Steak Joynt only on a couple of very special occasions but remember it vividly. Its decor resembled an opulent nineteenth-century bordello and was dominated by a huge painting of a voluptuous, Rubenesque nude.

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