Weekend Getaway Guide to Galena Illinois for History, Adventure and Culinary Delights

Theresa Demaria Avatar
Things to do in Galena Illinois - view of Main Street downtown with tall brick buildings lining both sides of the street, cars driving away and several pedestrians on the sidewalk.

The writer was hosted.

Intrigued by the past, enamored with the outdoors, and captivated by exquisite cuisine, Galena, Illinois, offers a remarkable tapestry of year-round experiences. An easy day trip from Chicago, I discovered during my visit that this charming town along the Mississippi River is a place where the past comes to life, the scenery takes your breath away, and the cuisine leaves you craving for more.

Here are the top things to do in Galena, Illinois, that I experienced during my visit.

History and Architecture

Downtown Galena’s Main Street

Just minutes from the Galena River Trail, I started my weekend getaway with a leisurely stroll down Historic Main Street to visit a cafe, antique stores, boutique gift shops, and the exquisite River Bend Gallery. 

Lined with well-preserved 19th-century buildings, this picturesque street is a delightful way to soak in the Midwest town’s rich history and architectural beauty.

Things to do in Galena Illinois - Ulysses S. Grant House. A two-story red brick building with green shutters, a green grass lawn, US flag flying on a flagpole and a white picket fence.
Ulysses S. Grant House, Galena, IL Photo credit: Istock

Ulysses S. Grant Home Tour

Stepping back in time, I embarked on a tour of the Ulysses S. Grant Home, a National Historic Landmark. This beautifully preserved residence provided a glimpse into the life of the 18th U.S. President. Walking through the rooms where Grant once lived was a fascinating historical journey.

Scenic Tours

Amelia’s Galena Ghost Tours 

Led by knowledgeable guides, these paranormal ghost tours offer captivating journeys through Galena’s historic streets, sharing tales of hauntings, ghostly encounters, and local legends.

We explored the city’s eerie side, visiting historic sites and hearing spooky stories that add a supernatural dimension to our visit to Galena. These tours provide a unique blend of history and mystery, making them a favorite attraction for those intrigued by the paranormal.

Things to do in Galena Illinois - Retro style trolley with green top and red bottom drives down a street next to a green lawn and trees.
Retro Style Trolley Photo credit: Istock

Galena Trolley Tours

One of the highlights of my visit was the Galena Trolley Tour. This informative guided tour allowed me to explore the Galena area’s rich history while enjoying breathtaking views of the rolling hills.

It was the perfect way to learn Galena’s history as we passed the area’s many top attractions, including the Washburne State Historic Site, the Galena Canning Company and The Dowling House at Belvedere Mansion, Galena’s oldest house.

Outdoor Activities

Things to do in Galena Illinois - Skiers ski down a mountain slope while chair lifts take others to the top.
Skiers enjoying the mountain. Photo credit: Istock

Skiing in Galena

During my visit, I couldn’t resist the allure of Chestnut Mountain Resort. In the winter, it offers skiing and snowboarding on 19 different trails. In the warmer months, the resort transforms into an adventure playground with activities like the Alpine Slide, self-guided Segway tours, and exhilarating zip-lining.

Things to do in Galena Illinois - Grand Park. A Civil War era cannon faces a green lawn with red brick downtown buildings and trees in the background.
Grant Park, Galena IL. Photo credit: Istock

U.S. Grant Park

This park is a serene oasis that pays tribute to Ulysses S. Grant. Amidst its tranquil surroundings lies a life-sized bronze statue of the 18th U.S. President, creating a moment of historical reflection. As you stroll through this beautiful park, you’ll feel a profound connection to the past and a sense of tranquility that makes it a must-visit destination in Galena.

Thunder Bay Falls

While my cool weather visit did not allow for a visit to Thunder Bay Falls, I hope a future trip to Galena will allow time for me to explore the area. Kayak rentals are available.


Whether you are a weekend or scratch golfer, there’s a Galena area golf course to fit your style. There are 5 courses in Galena and 12 more within a 20-mile radius. Stay at Eagle Ridge Resort, home to four award-winning golf courses.

Where to Eat and Drink in Galena

Things to do in Galena Illinois - Two bunches of green grapes hang from a grapevine with blurred background of green grass and wooden stakes.
White wine grapes. Photo credit: Istock

Galena Brewing Company

As a fan of craft beer, I couldn’t resist taking a tour of Galena Brewing Company. The brewery’s craft beers, each with its unique flavor profile inspired by local ingredients, were a treat for my taste buds. It was a delightful way to savor the local flavors.

Galena Cellars Vineyard Winery

One of the highlights of my trip was visiting Galena Cellars Vineyard & Winery. This winery offers a wine-tasting room and vineyard tours. I had the chance to sample the award-winning wines while taking in panoramic views of the stunning countryside.

Fried Green Tomatoes

For a romantic evening out, I dined at Fried Green Tomatoes. This restaurant offers Italian-inspired steak and seafood dishes that left me craving more. The combination of exquisite cuisine and a charming ambiance made for an unforgettable dining experience.

Log Cabin Steakhouse

A classic in Galena, the Log Cabin Steakhouse exceeded my expectations. I indulged in mouthwatering steak and seafood options in a rustic setting. It was a culinary journey that showcased Galena’s gastronomic excellence.

History and Culture in Galena

Galena History Museum

Immersing myself in Galena’s rich history was a must, and the US/Galena History Museum provided the perfect opportunity. From the city’s bustling 19th-century river town origins to its Civil War legacy, the museum offered a deep dive into the region’s past.

Where to Stay in Galena

Things to do in Galena Illinois - The Bed and Breakfast at Jail Hill Inn. Square red brick, 3-story building in Italianate style with a wrought iron fence in front and trees behind, at dusk with exterior and interior lights turned on.
The Bed and Breakfast at Jail Hill Inn, Photo credit: Jail Hill Inn

The Jail Hill Inn Bed and Breakfast offers exceptional service, warm hospitality, luxurious accommodations with modern amenities, gourmet breakfasts featuring fresh, locally sourced ingredients, a prime location near Galena’s Main Street, and historical charm in a meticulously restored 19th-century building.

Editor in Chief- Forest & Bluff Magazine Senior Style Director/Fashion Editor all four publications of JWC Media. Produce and art direct 20+ shoots per month in the Chicagoland region. Experienced freelance Fashion Stylist with a demonstrated history of working in the entertainment industry. Strong arts and design professional skilled in Trend Analysis, Photography, Luxury Goods, Advertising, and Trend Forecasting.
Read full bio

Leave a Reply

Your email address will not be published. Required fields are marked *