What’s Happening in Galena – Shops, Restaurants and Events!

by Nikki Lindholm

Imagine a town where 85% of the buildings are listed on the National Register of Historic Places,  the shopping and restaurants reside on a Main Street nicknamed ‘Helluva Half Mile,” there is a beautiful backdrop of hilly terrain and a calm winding river and you have yourself Galena, Illinois!

Galena has a rich, presidential history that predates the Civil War which can be easily seen and felt throughout the town. Ulysses S. Grant and his family moved to Galena in 1860. After he returned from the Civil War and was encouraged to run for president, he ran his presidential campaign from rooms in the DeSoto House, a hotel with a notable history of its own, even once named the “largest hotel in the West.” Today you can visit both the DeSoto House and the home that Grant and his family lived in upon his return as a war General.

Galena is a memorable town due to its beauty, history, and unique location that residents love living here, and tourists close and far continue to visit making Galena a favorite town for many midwesterners. The agents in our Galena office shared their favorite places to dine, shop, and explore in Galena.


Breakfast & Coffee

Start your day with a flakey croissant pastry and a cup of joe from Galena Bakehouse. You won’t regret it, their pastries are “hand laminated in-house using the finest European butter and chocolate. ” They also offer gluten-free options for breakfast and lunch. Their empanadas are a must-order! Eating at Bread and Vine Bakery is a mood. It’s fresh, fun, and vibrant, which makes it a perfect spot to grab a delicious bite. Make sure you take a pastry or five with you as they are equally as good! Family-owned and operated Trolley Depot Coffee Shop is a local favorite! The coffee shop’s name pays homage to the city’s infamous trolleys which happen to be located behind the store. Stop in for coffee or tea and stay for breakfast or lunch! If you’re like other Galenians and love their coffee, join their Coffee Club, a subscription box of Trolley Depot coffee and goodies!

Big Bills has it all from coffee to sandwiches, soups, pastries, and even Italian Ice. And they don’t mess around with their coffee devotion, evident by their “Death before Decaf” apparel!

“A little German, a little French, a little bistro!” Fritz and Frites have a little bit of everything when it comes to traditional savory dishes including Escargot and Wienerschnitzel!

Fried Green Tomatoes blends historic, local charm with great eats. The building which houses Fried Green Tomatos is dated back to the mid-1800s and even has ties to Ulysses S. Grant! Owner, Fred Bonnet, was careful not to destroy the history of the building, ” The history of the building Mr. Downling builds it part of the experience for our guests.”

Cannova’s Pizzeria is your quintessial family-owned pizzeria. Cannova’s specializes in all your favorites from pizzas to pasta. Their appetizers also deserve a mention, especially their charcuterie platter.

It’s not often you find a restaurant that has been operational for almost 100 years, even in Galena! Log Cabin Steak House has been continuously operating since 1927 and it’s one of Galena’s oldest dining establishments. It should come as no surprise that the food offered at such an established restaurant consists of mouthwatering steak and beef options as well as decadent seafood.

Stop by Jamies Wine and Bourbon Bar to sample and buy wine from small family-owned wineries near and far from the Midwest.



The moment you step into Isabella’s Ltd. Home Interiors and Gifts you know you have found your go-to home interiors store. Not only is the shop decorated to perfection, but the mix of traditional items with a modern twist can help elevate any home.

What’s better than finding a new book? Finding a new book at Galena Book & Paper.  In addition to classic favorites and the best sellers of the day Galena Book & Paper has beautiful stationery and cards in addition to interesting lithographs that would look amazing in a library or study. It’s a joy to peruse around this shop as well as to see the antique knickknacks showcased throughout the store.

Bella Rosa imports fine Italian apparel, silks, blends, and accessories.

A store where you can shop for clothes, accessories, and coffee but also buy gelato is a store model we need to see more of!   Elle and Beck’s has stylish clothes and shoes and can also satisfy your sweet tooth. It’s a win-win.

Community Events

Now in its 28th year, the Cemetery Walk at Greenwood Cemetary is a beloved event for those who love historic performances. Local performers portray the rugged lives of early settlers and share their stories. Galena has a rich and diverse history which enriches the stories of prosperity and challenges for those in the last 1800s.

Galena’s Country Fair is held in the early days of fall on Columbus Day Weekend. What started as a small event with only a few booths in Grant Park grew over the years to include 100 vendors, live entertainment, raffles, auctions and more. It’s the perfect fall event!

Start your Oktoberfest festivities with a bang, literally! Galena’s Oktoberfest begins with a cannon blast at noon to announce the fest has started. Of course, there will be the main Oktoberfest staples such as German-style food and beer as well as polka music, beer stein endurance tests, and authentic apparel. Also, it’s a day for the dogs, especially Wiener Dogs. There is a Wiener Dog Parade, a best-dressed contest, and last, a high-stakes race!

Every December, Galena comes alive during Luminaria, an event held right before the holidays where 5,000 candlelit luminaries line the streets, steps, sidewalks, and store windows of Main Street. It’s a beautiful way to experience glowing Galena during its picturesque winter season.

To learn more about the Galena area and what it has to offer like community events and favorite shops – check out our Galena community page. View homes for sale, find an agent, and learn more about the town bursting at the seams with history!

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