Galena, Illinois
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One Helluva Half Mile

Spend a day (or two!) shopping Galena’s historic Main Street

By Margaret Doyle

People in line for a ghost tour in Galena, IL

Chicago might have a “magnificent mile” but Galena proudly lays claim to one Helluva Half Mile. You won’t find any cookie-cutter, brand name stores here. Instead, Galena’s Main Street is all about the unique, local mom ‘n’ pop independent shops you can’t find anywhere else. In fact, Galena has been recognized as one of America’s Greatest Main Streets by Travel + Leisure magazine.

Helluva history

One of the first things you notice as you stroll along this curved Main Street are the beautifully preserved red brick buildings that date back to Galena’s days as a booming 1800s lead mining town. Steeped in history, 75% of the town is listed on the National Register of Historic Places. Today, the Federal-style buildings house more than 125 quaint boutiques, art galleries, restaurants and bars. The picturesque hills surrounding the town are dotted with opulent former mansions built by wealthy steamboat captains and mine owners that have been turned into luxurious bed and breakfasts.

People in line for a ghost tour in Galena, IL

Ride with Galena Trolley Tours and you’ll learn the fascinating stories behind these elegant Victorian mansions, plus see historic sites that include the Grant Home, the former residence of President Ulysses S. Grant that was gifted to him by the people of Galena as thanks for his service during the Civil War.

Pedestrians and cars on Main Street-aka, the Helluva Half Mile-in Galena, IL

Main Street shopping

Main Street is an exciting place to shop for one-of-a-kind gifts or to buy something special just for you. Bring home a unique piece of Galena from Pinder Pottery, where you can watch the artist spin clay into beautiful stoneware teapots, bowls and plates. Outside the Lines Art Gallery represents a variety of area artists, who create everything from beautiful watercolor paintings depicting town and country landscapes to ceramic sculptures and jewelry. Pick up a bottle of wine from the award-winning Galena Cellars Vineyard & Winery, which has a tasting room in a restored brick 1840s granary in town.

Pedestrians and cars on Main Street-aka, the Helluva Half Mile-in Galena, IL

Poopsie’s is a playland for adults and kids alike. You’ll find fun games and books, as well as funky home accent pieces. Clothing stores, such as Ethyl’s and Honest John’s Emporium, offer chic women’s clothing that will take you from shopping in the day to a romantic dinner at night. Accessorize your outfit with an exotic Indonesian bracelet or handmade Celtic necklace from Beyond the Horizon.

If you’re looking to feather your nest, Main Street features some great home decor stores. Isabella’s Ltd. sells repurposed and up-cycled furniture that has been beautifully painted and reupholstered. Galena Metal Artworks crafts cool cast iron tables and lamps, as well as outdoor sculptures. All That’s Vintage specializes in 1950s pieces that will add a retro flair to your abode.

Pedestrians and cars on Main Street-aka, the Helluva Half Mile-in Galena, IL

Of course you have to order the fried green tomatoes, served breaded and topped with cheese and marinara sauce.

Dining destinations

Get a real taste of Galena at one of its Main Street restaurants. 111 Main sources ingredients from local farms and purveyors to create dishes that are truly farm-to-fork. Exposed brick walls, warm woods and big black-and-white photos of farmers on the walls create a sophisticated, earthy ambiance. Fried Green Tomatoes, known for its rustic Italian dishes, is located in a former leather goods shop owned by the family of Ulysses S. Grant. Galena‚Äôs Helluva Half Mile includes shopping and fine dining Of course, you have to order the fried green tomatoes, served breaded and topped with cheese and marinara sauce. Relax in the supper club atmosphere of the Log Cabin Steakhouse, which has been run by the Rigopoulos family for more than 40 years. The menu features a selection of hand-cut steaks and seafood but the real crowd pleaser is the flaming saganaki, served with a fiery “Opa!” flourish. Fritz and Frites offers the unique pairing of German and French dishes (think sauerbraten and steak frites) in a charming, European-style bistro setting.

Don't miss the Wedding in a Window in Galena, Illinois

Main Street after dark

Main Street takes on a lively after-hours vibe when the sun goes down. Raise a pint and see local bands at Galena Brewing Company. Be sure to sample a beer flight that includes the brewery’s award-winning ales (like the Farmer’s Blonde Ale) and seasonal lagers. Cap off your evening with a dessert cocktail (the chocolate-raspberry Truffle Tini is sinful) at Miss Kitty’s Grape Escape, where you can listen to live music, ranging from bluegrass to rock.

Stay the night at Main Street’s historic DeSoto House Hotel, Illinois’ oldest operating hotel, which served as the campaign headquarters for Grant when he ran for president in 1868… and won! Other famous figures that have visited the DeSoto House include Abraham Lincoln, who spoke from the hotel balcony to a crowd gathered on the street below.

Night of the Luminaria

Perhaps the most magical time to visit Main Street is during Night of the Luminaria, held Dec. 10, when the entire town is illuminated by an amber candlelight glow from 5,000 luminaries that line the streets and sidewalks. Businesses stay open late for holiday shoppers and revelers. Earlier in the day, don’t miss the 3 p.m. Wedding in a Window, when a lucky prize-winning couple will actually get married in a storefront window on Main Street.

Don't miss the Wedding in a Window in Galena, Illinois