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

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! The Bowl and Roll opened in the same spot, although the furnishings were replaced. 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

The Earl of Old Town

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


Filed under Art and Culture, Chicago, History, Nostalgia, Pop Culture, Shopping

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

  1. David Fink

    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.

    • Betsy

      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.

  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.

    • Betsy

      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.

  4. Nancy

    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!

  5. David Zornig

    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.


    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. Pat Somogyi

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

  8. Solczyk Bob

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

    • Betsy

      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. Tony E

    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.

    • Betsy

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

  10. Diane Rohs

    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 and as I recall really great pizza, but we also found a peep hole in the women’s bathroom – lol. Very fond memories. Thank You!

    • Betsy

      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.

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