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Old Town neighborhood guide

Where to eat, shop and other things to do in Chicago’s Old Town neighborhood.

Video by Brian Rich with James Foster

There’s plenty of “new” in Old Town, but when I visit the neighborhood I’m drawn to the “old.” During my visit I wanted to focus on some of the oldest establishments that have bucked trends and survived changing times, continuing to do business in much the same way for generations.

Old Town is known for its beautiful architecture, quaint streets and independently-owned shops. The neighborhood is so old that many streets here predate the Chicago grid system and are diagonal. Well known landmark, St. Michael Catholic Church, is here. Its bells have been welcoming visitors since 1852. The Second City makes its home in Old Town and continues to be the launching point of stars.

Besides some of the well known spots in the neighborhood, I want to highlight a few hidden gems. One of those is the Midwest Buddhist Temple. From the temple’s perch, you can see the towering bell spire of St. Michael’s. Also, one of Chicago’s most prolific artist’s life works is hidden in the neighborhood. Edgar Miller may be someone you’ve never heard of, in large part because his art lives on in private residences.

Video by Brian Rich with James Foster

Old Town is a very walkable neighborhood with beautiful old homes and a variety of restaurants and businesses that will please the choosiest of consumers. That’s why I think it’s the perfect neighborhood to take out-of-town visitors and for going out with friends or on a date. There’s plenty of old-school traditional choices, quirky boutiques and modern establishments to impress anyone!

History of Old Town

It all started as a cabbage patch

In the 1800s, German immigrant farmers moved to the meadows around North Avenue. The former marshland was used to grow vegetables, including cabbage. The area garnered the nickname “Cabbage Patch.”

In Shirley Baugher’s book “Hidden History of Old Town,” she notes German immigrants were drawn to Chicago because of the “city’s vigorous and supportive Catholic Church” and moved to farm the dried-up marshland of Old Town because “the lure of free or cheap land was irresistible.”

The Chicago Diocese authorized the founding of the St. Michael Parrish in 1852. After a successful German brewery owner, Michael Diversey, donated property to the church, that same year a small church was built that welcomed 42 families.

In 1869, a magnificent church with a 200-foot steeple was built – only to be tragically burned down by the Chicago fire that destroyed much of the city. However, the red sandstone brick walls of the church withstood the fire, and St. Michael parishioners rebuilt in 1872.

The Great Chicago Fire in 1871 destroyed much of Old Town, but houses were rebuilt – lots of them. With the new housing stock came demographic changes, according to Baugher. Eastern Europeans, Irish, French and Italians moved to the neighborhood. In addition, Japanese, Assyrians and Filipinos had also moved in. Many African Americans who worked for wealthy families in the Gold Coast also made homes in Old Town.

With the turn of the century, the Cabbage Patch eventually gave way to the name “North Town.” At the time, the neighborhood sat near the edge of the northern border of the city.

The 1900s were also a time when Chicago was very important in the film and movie industry. Chicago production house, Essanay Films, was known for movies featuring Charlie Chaplin. Many of the hired actors for the company, including Gloria Swanson, lived in the Crilly Court apartments in Old Town.

In 1924, Crilly Court was also headquarters for the Society for Human Rights, the first-ever American gay rights organization founded by German immigrant Henry Gerber. Gerber published the newsletter, “Friendship and Freedom.” This newsletter was the country’s first documented publication advocating for civil rights for the gay community. The Henry Gerber home became a Chicago landmark in 2001 and a national historic landmark in 2015.

The 1920s and 1930s brought many artists to the neighborhood. It was a time of boundless creativity brought on by bohemians, revolutionaries, progressives and writers.

At the center of this artist colony was Chicago artist Edgar Miller. An artist who worked in every medium, he incorporated his carvings, sculpture, tile work and stained glass into fully realized studios (the Carl Street Studios) and apartments. (More on Miller later.)

In the late 1940s, North Town residents organized annual art fairs called “Old Town Holiday.” The name Old Town stuck after that and so did the art fair.

A vintage Old Town Triangle street map | Courtesy: The Old Town Triangle Association
A vintage Old Town Triangle street map | Courtesy: The Old Town Triangle Association

Old Town was also frequently referred to as the “Old Town Triangle” thanks to a civil defense map drawn up during World War II that was in the shape of a triangle. That triangle was formed by Clark, North, and Ogden streets. While Ogden Street was closed to traffic between North Ave. and Armitage Ave in 1967, use of the “Old Town Triangle” name continued. For example, there’s the Old Town Triangle Association neighborhood group that hosts the annual Old Town Art Fair and the area itself is designated as the Old Town Triangle Historic District.

Through the years, the population of Old Town has changed quite a bit. After WW2, many established families moved to the suburbs which opened up housing for new residents, including new minority groups. For example, beginning in the 1950s Puerto Ricans became one of the largest minority groups in the neighborhood. (As a result of urban renewal, many wound up moving to the suburbs and to other parts of the city, including Humboldt Park.)

The 1960s brought the counter-culture movement to Old Town. It was the nexus for hippie culture and was also welcoming to gays and lesbians and considered Chicago’s “gayborhood” at the time.

Old Town School of Folk Music

During this time there was a resurgence of folk music as well. Along with the gay and lesbian bars, eclectic shops and music clubs were abundant.

Old Town School of Folk was established in December 1957. Its original location was at 333 North Ave. in Old Town. Pete Seeger and Mahalia Jackson were some of the many artists who performed at the Old Town School in its early years. In the 1960s, the school helped launch the careers of Roger McGuinn of the Byrds, Bob Gibson, John Prine, Bonnie Koloc, and the late Steve Goodman who all studied at the school.

Old Town School co-founders Frank Hamilton (left) and Win Stracke (right) perform on opening night, December 1, 1957. | Kiko Konagamitsu/ Courtesy of the Old Town School Resource Center
Old Town School co-founders Frank Hamilton (left) and Win Stracke (right) perform on opening night, December 1, 1957. | Kiko Konagamitsu/ Courtesy of the Old Town School Resource Center

In 1968, the school moved to 909 West Armitage in Lincoln Park. In addition to this location, the school has a 43,000 square foot flagship location in former Hild Library, in Lincoln Square at 4544 N. Lincoln Ave.

For a more in-depth look at the history of Old Town and its designated Old Town Triangle Historic District, check out Shirley Baugher’s “ Hidden History of Old Town.”

Also, the Old Town Triangle Association is a wonderful resource, has a collection of historical photos and has an art center with workshops and classes. The association is also the organizer of the Old Town Art Fair.

And as always, the Chicago History Museum -which is on the eastern edge of Old Town-has programs, events, resources and walking tours.

Things to do in Old Town

As mentioned in the history of Old Town, St Michael Catholic Church is a must-see. Designed by architect August Walbaum, it won’t be hard to find as the 290-foot spire is easily spotted from various points in the neighborhood.

Inside are five beautiful, ornate alters painted in the Baroque style. One of them, “Our Mother of Perpetual Help” survived the Great Chicago Fire. The stained glass windows were installed in 1902 to celebrate the church’s Golden Jubliee. There’s also a wooden “Last Supper” carving that dates back to Chicago’s World Fair in 1893. If you attend mass on Sunday at 11 a.m., you can hear the 1925 Kilgen pipe organ.

The Midwest Buddhist Temple was founded in 1944. Many Japanese Americans relocated to Chicago after being placed in relocation and interment camps during World War II. Many chose to relocate to the Midwest and East coasts, as they still faced a lot of resistance and racism on the West coast.

Reverend Gyodo Kono relocated to Chicago after being released from an internment camp in Arkansas. He saw a need for a Shin Buddhist temple and a gathering space for the growing Japanese-American community. The Temple of Enlightenment was dedicated in November 1971. A garden was added in 2014. The temple welcomes all, has tours and classes from meditation to cooking.

Old Town’s artistic genius: Edgar Miller

Edgar Miller may be one of Chicago’s most prolific artists you’ve never heard of. At the height of the Chicago Art Renaissance, he worked in over 30 mediums. He was a painter, master woodcarver, sculptor and one of the nation’s foremost stained-glass designers.

During his lifetime much of his genius was overlooked because his work was difficult to categorize and was incorporated into the homes he created. In the 1920s, he would use mixed and found materials to “Edgarize” homes – filling them with his creations of stained glass windows, murals, tile mosaics, wood carvings and frescoes.

Edgar Miller Legacy is a non-profit organization that works to preserve the often over looked artist’s legacy. He designed and executed hundreds of interior and exterior spaces, installations, sculptures and murals. Most of his work now exists in privately-owned residences like the Carl Street Studios in Old Town.

Through the Legacy foundation, you can book a tour to visit the studios and see other work by Edgar Miller. These tours are extremely limited and offered only a few times a year. It’s important to book in advance through the organization’s website.

The Old Town Art Fair

The Old Town Art Fair is a juried fine art fair that includes a Garden Walk, music stages and other family-friendly activities. Held in June, it’s the biggest event of the year in Old Town and features more than 250 nationally acclaimed artists and more than 30,000 people attend yearly. The Old Town Art Fair has been organized by the Old Town Triangle Association for more than 70 years.

The Old Town Art Fair has been drawing big crowds for more 70 years. This photo is from 1959. | Sun-Times Archives
The Old Town Art Fair has been drawing big crowds for more 70 years. This photo is from 1959. | Sun-Times Archives

The Old Town Art Fair also includes a Garden Walk. Around 50 private residences in the historic Old Town Triangle open their backyards and gardens for the public to view and enjoy.

The very same weekend the Old Town Art Fair is happening, there’s another art fair underway in the neighborhood!

The other, younger art fair in Old Town is called the Wells Street Art Festival. It has 225 juried artists, along with stages for live music. This festival runs later into the evening and is run by the Old Town Merchants and Residents Association.

Of the two, the Wells Street Art Festival is a bit rowdier and is held on Wells Street which is lined with restaurants and bars.

The Second City and other fun stuff

In 1959, Bernie Sahlins, Paul Sills and Howard Alk opened The Second City on 1942 N. Wells St. In 1967, the theater moved to 1616 N Wells St., which remains its current address.

A Second City Main Stage Production: “Fool Me Twice, Deja vu” with Chelsea Devantez Daniel Strauss Jamison Webb & Rashawn Nadine Scott | Todd Rosenberg Photography / Sun-Times Archives
A Second City Main Stage Production: “Fool Me Twice, Deja vu” with Chelsea Devantez Daniel Strauss Jamison Webb & Rashawn Nadine Scott | Todd Rosenberg Photography / Sun-Times Archives

The world’s premiere improv and comedy school seems to have an endless roster of successful alum who have gone on to star in Saturday Night Live and conquer the Hollywood box office. Gilda Radner, John Belushi, Dan Aykroyd, Martin Short, Eugene Levy, Bill Murray, Tina Fey, Amy Pohler, Steven Colbert and Steve Carrell are just a few of the alums who have gone on to become superstars.

Check out the website to plan your visit, see a show or sign up for classes. The Second City has multiple stages and shows to choose from.

Zanies Comedy Club is celebrating its 40th anniversary this year. It’s a comedy club that books national comedians like Jay Leno, Kevin Hart and Jerry Seinfeld – and has stand-up comedy 7 nights a week. There are no open mic nights and a two-drink minimum. Zanies is Chicago’s longest running stand-up comedy club. It’s worth every penny.

Zanies in Old Town | Tyler LaRiviere/Sun-Times
Zanies in Old Town | Tyler LaRiviere/Sun-Times

A Red Orchid Theater seats 70 audience members and was founded by actors Guy Van Swearingen, Larry Grimm and Michael Shannon (The Shape of Water, Boardwalk Empire) in 1993. It’s an intimate space and a keystone of the Chicago’s theater scene. It’s somewhat of a hidden gem in the Old Town neighborhood, with a narrow storefront on Wells Street.

A Red Orchid Theater is an independent theater committed to presenting new and rarely seen works with high quality production standards. The theater was a 2016 recipient of the MacArthur Award.

Place to eat and drink

One of my favorite things about Old Town restaurants is that many are multi-generational. There’s definitely a newer element of nightlife on Wells Street with clubby bars and modern sleek spaces, but my picks tend to be the “old school” joints in the neighborhood.

Kamehachi means “eight turtles” in Japanese. The number 8 and turtles are two auspicious symbols in Japan. It’s worked for Chicago’s “first sushi restaurant” for more than 40 years. The restaurant has moved a few times in its history but has always remained in Old Town. Opened in 1967 by Marion Konichi, it still remains all in the family. She now runs it with her daughter Sharon Perazzoli.

Ji Suk Yi with Marion Konichi (center) and her daughter, Sharon Perazzoli of Kamehachi Restaurant in Old Town | Brian Rich/ For the Sun-Times
Ji Suk Yi with Marion Konichi (center) and her daughter, Sharon Perazzoli of Kamehachi Restaurant in Old Town | Brian Rich/ For the Sun-Times

Orso’s and Topo Gigio are two of Old Town’s favorite old-school Italian restaurants.

Orso’s also has been around for more than 40 years, and the ambiance is romantic, bling and breathtaking. You’ll find multiple crystal chandeliers, a baby grand piano, charming bar and walls lined with celebrity and family photos. The back patio is shaded by a grape vine that has grown over the years along with the family business.

Topo Gigio is celebrating 30 years of business in the Old Town neighborhood. The sidewalk patio is usually packed, and the servers know their regulars by name. It’s a great people-watching spot, and the service is great.

A new restaurant in the neighborhood that’s my new favorite is Two Lights Seafood and Oyster. The decor is modern, fresh and bright. You can get your oysters raw or hot and spicy – Nashville hot style. There’s green curry lobster stew, crudo, poke tacos and a simple fish sandwich. It’s casual enough to hang out at the roomy bar solo or for date night. The husband and wife team behind The Tortoise Club in the Loop know how to do casual and classy all in one.

Lasagna and jalapeño gnocchi at Orso’s in Old Town | Ji Suk Yi/ Sun-Times
Lasagna and jalapeño gnocchi at Orso’s in Old Town | Ji Suk Yi/ Sun-Times

Twin Anchors makes its home in a building that dates back to 1881. According to owner Mary Kay Tuzi the building has been some sort of tavern since the 1890s. Twin Anchors came about shortly before the end of prohibition in 1931, the brain child of Captain Herb Eldean (a harbor master who could access liquor from Canada) and Bob Walters. Walters’ wife was known to make ribs on Sundays for customers and those ribs are still the best sellers at Twin Anchors today.

Tuzi’s father, an insurance salesmen, purchased Twin Anchors in 1978 and moved his wife and children (sons- ages 19 and 18; daughters- ages 16 and 9) to Old Town from the suburb of Glen Ellyn. “Everyone thought that we were crazy but I was excited. I never thought I’d be doing it forty years later,” said Tuzi.

Tuzi and her siblings run the restaurant and are celebrating 40 years this year. She remembers that the neighborhood was working class and rough at times. Now it’s mostly families and affluent. It’s also a place where the famous have dined (Frank Sinatra, Conan O’Brien, Payton and Eli Manning) and movies have been filmed (Return to Me, The Dark Knight).

Whether it’s celebrities, tourists or former residents taking a walk down memory lane, Twin Anchors is a neighborhood place. It’s busy, friendly, charming and delicious. The Tuzi family is the third family to have owned the restaurant and they pour their heart and soul into the quality of food, service and preserving its history.

Grilled jumbo shrimp at Twin Anchors in Old Town. | Ji Suk Yi/ Sun-Times
Grilled jumbo shrimp at Twin Anchors in Old Town. | Ji Suk Yi/ Sun-Times

Tuzi started a tradition of gifting servers who reached 25 years with the company a gold anchor diamond necklace pendant. One server, Betty, has been there for 39 years. Servers Tina, Debbie, Surass and Arnie have all put in over 25 years of service.

“It’s about longevity. Twin Anchors is about family… with the customers, the employees. That’s what makes it so special,” said Tuzi.

Old Town Ale House is a “must do” when in Old Town. It’s cash only, and there’s just one TV. Instead, come to admire the artwork of owner Bruce Cameron Elliot all over the walls. Open since 1958 and in its current location since 1971, this dive bar has been a favorite of locals and luminaries alike.

Featured on Anthony Bourdain’s Parts Unknown in 2016, a favorite of Sun-Times legends Roger Ebert and Mike Royko, it’s also been the preferred watering hole of choice to Second City comedians and Red Orchid theater actors. The juke box plays mostly jazz (no pop, rock, hiphop or rap) in order to keep the ambiance about conversation and less about partying.

Old Town Ale House in Old Town. | Tyler LaRiviere/Sun-Times
Old Town Ale House in Old Town. | Tyler LaRiviere/Sun-Times

La Fournette is one of my favorite bakeries in the city. I discovered it after eating the bakery’s bread at a restaurant. I couldn’t stop eating the baguette and inquired where it was from. Voila! My love affair with la Fournette began. The bakery is run by a former instructor at Chicago’s Pastry French School, Pierre Zimmerman. He’s recreating the roots he had in his family’s bakery in Alsace, running the bakery with his wife and kids in Old Town.

The Fudge Pot has been satisfying chocolate cravings since 1963. Dave Dattalo is the second generation owner of the sweets shop. Dattalo’s father worked at Mars Candy Company in the 1930s and learned everything about candy and later opened his own shop. Soon the family business will pass on to a third generation of family ownership as Dattalo looks to retire. My recommendation is to buy the Old Town Classic four-pound assortment of the stores’s most popular chocolates. Too much? Ok, I’d recommend the almond bark and the sea-salted caramels.

Where to shop

Old Town Aquarium in Old Town. | Tyler LaRiviere/Sun-Times
Old Town Aquarium in Old Town. | Tyler LaRiviere/Sun-Times

GreenHeart Shop is the perfect place to buy a gift if for the conscious consumer. It’s a fair trade, non-profit boutique where every item comes with a story – whether it’s fair trade, eco-conscious or has a social mission. GreenHeart sells everything from home goods to jewelry to items for the baby.

Judy Maxwell Home is named after Barbra Streisand’s character in “What’s Up, Doc?” If you’re looking for that eclectic, quirky gift for that person in your life who’s impossible to buy for, this is the shop for you! It’s part home goods gift shop and fun museum. The owner is none other than actress Joan Cusack. I think the store reflects the quirky characters she often plays.

Old Town Oil has premium olive oils and vinegars that will take your cooking to another level. It’s also great as a gift for the cook in the family or as a host gift. It’s an interactive experience; you’re encouraged to sample and try the products sourced from small batch suppliers.

The Spice House is another boutique that’s a must for chefs and home cooks. It has a vast collection of spices and herbs that can take your cooking around the world. One of my favorite shops to find gifts, The Spice House has Chicago neighborhood gift boxes, full of spices that reflect the ethnic flavors found in Chicago.

House of Glunz is Chicago’s oldest wine and liquor store. Opened in 1888 by Louis Glunz II, it is still family owned-and-operated. The shop survived the Prohibition era by selling medicinal spirits and sacramental wine. You can pop in for a bottle of affordable wine under $20 or inquire about specialty wines or spirits older than 100 years. The pub next door reopened in 2013 and also serves food.

Ji Suk Yi with Christopher Donovan of House of Glunz, Chicago’s oldest liquor store | Brian Rich/For the Sun-Times
Ji Suk Yi with Christopher Donovan of House of Glunz, Chicago’s oldest liquor store | Brian Rich/For the Sun-Times

One more thing

When I visit Old Town, it feels like NYC’s Greenwich Village. The neighborhood streets are dreamy and romantic. The history is palpable along the tree-lined streets dotted with old Victorian-era homes and multi-generational restaurants and businesses. You can still get glimpses of the Chicago Art Renaissance that helped create the foundation for this beautiful neighborhood. The bohemian and eclectic still lives on in the old-school spots and are awaiting to be discovered again.

It’s a neighborhood full of nostalgia and future possibilities. It’s great to watch a revue at The Second City and think about all of the famous artists that started there and marvel at students as they pursue those same dreams. It’s fulfilling to dine at restaurants where American dreams have been realized – stalwarts of the neighborhood despite changing times. The care and commitment to stay, day in and day out, for multi-generations in a business goes beyond just making a living but speaks to something more – a family legacy and love for your neighbors.

I hope you’ll go to Old Town and take the time to rediscover what makes it stand the test of time, what’s new and some of its hidden gems. See you next time on The Grid!

Rubye Lane also contributed to this report.

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