Old Town didn’t officially become Old Town until the 1940s. During World War II, the triangular area bordered by North Avenue, Clark Street, and Ogden Avenue, which ran up to Lincoln Park until the 1960s, was designated a “neighborhood defense unit” by the Chicago Civil Defense Corps.
According to a 2008 Tribune article, Old Town is bounded by Division Street (south) to Armitage Avenue (north), and Clark Street (west) to Halsted Street (east).
The “Old Town” name was used again in 1948 when the same area residents formed the Old Town Triangle Association.
After the war was over, the neighbors maintained the spirit of their community by sponsoring popular annual art fairs they called the “Old Town Holiday," which later became the Old Town Art Fair.
Wells Street is Old Town's main street. In an age when people were fleeing the city for the suburbs and then urban renewal was leveling nearby areas, local small business owners dug in and Old Town became a medley of bohemian artists, trendy shops, flashy tourist spots, bars and taverns, and lots of restaurants. In the late-60s, Old Town became Chicago's hippie haven.
Maiden Lane at 1525 N. Wells Street, a shopping center that fits almost none of the conventional ideas of what a shopping center should look like opened May of 1966 with space for 20 shops. Maiden Lane was once a garage owned by Henry Susk of Susk Pontiac. Susk found the garage was being surrounded by the gift shops, antique stores, restaurants, and bistros that have changed the character of North Wells. He decided the building could be remodeled to create the atmosphere of the Old Maiden Lane section of London. A "lane" now runs thru the center of the building, lined with small shops reminiscent of London. Old English gaslights add to the illusion. Near the rear of the building the lane widens into a square with a fountain. Frank C. Wells, senior vice president of L.J. Sheridan & Company, Maiden Lane's leasing agent, said this may be one of the smallest shopping centers the firm has ever assisted in developing and leasing, but it is also one of the most interesting. Actually, Wells pointed out, Maiden Lane follows the latest concepts of shopping center design, including a heated covered mall, outstanding shopper circulation, and distinctive architecture. There are no giant department stores there, but you will find Granny's Toy shop, the Tye shop, the Smugglers Gift shop, Wiggery, and other interesting shops.
Piper’s Alley was opened in November of 1965 by Rudolph Schwartz and Jack Solomon, owners of the five buildings making up the 15 shops that once made up Piper’s Bakery and stables.
A giant Tiffany lamp hung outside the entrance to the maze of unusual retail shops. The businesses (during different periods of time) in Piper's Alley had names like the Bratskellar, Bustopher Jones Boutique, the Peace Pipe, "In" Sanity party goods store, the Glass Unicorne, Jack B. Nimble Candle Shop; Off the Hook decorator items, the Hair Shoppe, Aardvark Cinematheque movie theatre, the Caravan handcrafts store, Personal Posters instant immortality - photos to poster in 15 minutes, Charlie's General Store, Volume 1 Book Shop, the Jewelry Shop, Arts international Gallery, the Flypped Disc record store, the Sweet Tooth old fashioned candy, La Piazza Restaurant, Peace Pipe, Design India, Poor Richards, Male M1 Men's Shop, the Hungry Eye, Two Brothers, and Ye Olde Farm House restaurant. That Steak Joynt was said to be haunted as customers and staff members reported bizarre, supernatural experiences there for years. Customers walked down a brick alley lined with antique lamps.
|Charlies General Store|
|La Piazza in Pipers Alley, 1967|
|La Strada Restaurant in Piper's Alley, 1965|
|Chances R Interior|
The Pickle Barrel restaurant offered a small barrel of pickles and a bowl of popcorn at every table and a balloon artist wandering around the restaurant. The Fireplace Inn restaurant and bar featuring charcoal broiled ribs, steaks, seafood.
There was the Paul Bunyan restaurant, bakery (home of the 12" cookie) and Buzz Saw Bar, the Golden Dragon Cantonese restaurant, the Stage Coach Restaurant and Snack Shop, The Pup Room - Red Hots and Hamburgers restaurant, Beef & Bourbon restaurant, La Strada restaurant, Old Town Rib Shack, and least we forget Lum's Restaurant which was on the southwest corner of North Avenue and Wells Street.
It was home to the famed Second City Theater, Uno's Bizzare Bazzar head shop, The Fudge Pot, the Town Shop, Madge women's clothing store, Parlor Jewelry, a penny candy shop, the Wick-ed Shoppe - a candle store, and the Man at Ease - men's clothing store, Old Town Gate, the Old Town Auction House, the Oriental Gift Shop, Toptown clothing, Old Town Shop, The What Not Shop, and the Old Town Aquarium.
|The Fig Leaf and Paper Dress Store.|
The original Crate and Barrel store was on Wells Street where they displayed the glasses and dishware in wooden barrels and crates filled with straw.
The House of Horror was a spooky, creepy place for a kid to see. I had nightmares.
|House of Horrors was close to Lum's, across the street from the Emporium.|
Ripley’s Believe It or Not Museum at 1500 N. Wells Street opened with a party on the evening of November 21, 1968. Reportedly, more than 500 people showed up. Visitors were greeted with an optical illusion in the lobby. A giant floating faucet seemingly suspended in mid-air, the faucet spilled out a thick and endless flow of water into a pebbly pond. It was a simple illusion. A tall, transparent pipe held the faucet in place at the nozzle, blasting water upwards that immediately gushed back down the sides covering the pipe.
|Photo not from the Chicago Ripley's Believe it or Not!|
The Earl of Old Town Cafe & Pub at 1615 N. Wells Street was the fabled club that came to epitomize the Chicago folk scene and honed such home-grown talent as Steve Goodman, John Prine and Bonnie Koloc opened in 1962. Owner Earl Pionke didn't introduce music, however, until 1966. Several years later, Pionke opened a larger club, the Earl of Old Town on Harlem in Norridge. It closed four years later when the folk boom petered out. In late 1983 Pionke switched to a blues format and changed the name of the club to Blues at the Earl. And there was the Old Town School of Folk Music. Mother Blues, the Purple Cow, the Crystal Pistol, Quiet Knight and the Plugged Nickel were other very popular music venues.
LIVE - Miles Davis Quintet at the Plugged Nickel Club, Old Town, Chicago, Illinois.
December 22, 1965
1st Set [1:20]
2nd Set [1:08]
Steve Goodman Live at the Earl of Old Town, Chicago, Illinois. (date unknown)
Lincoln Park PiratesOld Town also catered to the under 21 crowd with dance clubs; Judy's Juniors, Like Young and My Sister's Place.
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The Piper's Alley March 1, 1971 Fire.
On Wednesday, August 26, a fire ignited inside of a grease chute above the kitchen in Adobo Grill on Wells Street in Old Town. The fire spread to the building housing The Second City, a comedy club and school of improvisation, destroying offices and memorabilia from alumni. Months after the accident, the community is still cleaning up the mess.
Firemen said all the shops on the first floor suffered smoke and water damage. The buildings were estimated to be worth $1½ to $2 million dollars.
On top of repairing fire damage, Second City is enduring construction in part of an expansion. Building onto what used to be the movie theaters in Piper's Alley, they have gutted all that and put in new stages. The expansion of Second City will be huge.
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Compiled by Neil Gale, Ph.D.