Love historic charm, rolling hills, and peaceful getaways? Then let me introduce you to Galena. Tucked into northwest Illinois near the Mississippi River, Galena feels like a step back in time—in the best way. The 19th-century architecture, charming shops, and welcoming atmosphere make it one of my favorite places to unwind. Whether I’m wandering the historic streets, learning about Ulysses S. Grant, or just taking in the scenery, this little town always leaves me smiling.

Best Time to Visit

I’ve been to Galena in every season, and honestly, each one has its perks. April through October is probably your best bet if you want to enjoy warm weather for shopping, hiking, or sipping wine on a patio. Summer’s lively, and fall? Absolutely stunning. The rolling hills light up with colorful foliage, and the harvest festivals make the whole town feel festive. Winter is quieter but still magical—think twinkling lights, cozy inns, and hot cocoa by the fireplace.

How to Get There

  • By Car: I usually drive in on U.S. Route 20—Galena is about 3 hours from Chicago and only 30 minutes from Dubuque, Iowa. It’s a scenic trip, especially as you get into the hills.
  • By Air: If you’re flying, Dubuque Regional Airport (DBQ) is the closest option and super convenient. If you’re coming from farther away, Chicago O'Hare (ORD) is the nearest major airport—just expect a longer drive (about 3.5 hours).
  • By Bus: Bus service is limited, and in my experience, having your own car makes it easier to explore the shops, trails, and wineries nearby.

Where to Stay

  • Jail Hill Inn – I stayed here for a birthday weekend once, and it was unforgettable. This former jail-turned-luxury B&B is one of the most unique places I’ve ever stayed. The rooms are stunning, and the gourmet breakfast? Worth waking up early for.
  • Irish Cottage Inn & Suites – For something cozy with a bit of character, I always recommend this spot. The pub downstairs has great comfort food, and you can even book a spa treatment after a day of exploring.
  • DeSoto House Hotel – If you love history, this is your place. President Lincoln once spoke here! It’s right in the middle of downtown, which makes it easy to walk to shops, restaurants, and historic sites. The old-world charm is real—but the rooms have all the modern touches you’ll want.

Top Attractions in Galena, Illinois

Ulysses S. Grant Home

Ulysses S. Grant Home

Ulysses S. Grant Home - Explore a preserved historic home and admire Civil War-era artifacts.                                    

Galena - Jo Daviess County Historical Society

Galena - Jo Daviess County Historical Society

Galena - Jo Daviess County Historical Society - Discover fascinating local history and engaging exhibits.                                    

Chestnut Mountain Resort

Chestnut Mountain Resort

Chestnut Mountain Resort - Enjoy exciting skiing, scenic views, and year-round outdoor adventures.                                    

The Elihu B. Washburne House

Courtesy of Berenike - Fotolia.com

The Elihu B. Washburne House - Visit a historic landmark and explore 19th-century political history.                                     

Old Market House

Courtesy of Ongala - Fotolia.com

Old Market House - Walk through a restored 1845 building and discover local heritage.                                     

P.T. Murphy Magic Theater

P.T. Murphy Magic Theater

P.T. Murphy Magic Theater - Experience an intimate, exciting magic show filled with surprises.                                    

Casper Bluff Land and Water Reserve

Courtesy of jdcf.org

Casper Bluff Land and Water Reserve - Walk along scenic trails and admire ancient Native American mounds.                                    

Linmar Gardens

Linmar Gardens

Linmar Gardens - Stroll through lush gardens and enjoy peaceful, artistic surroundings.                                    

West Street Sculpture Park

West Street Sculpture Park

West Street Sculpture Park - Explore unusual outdoor sculptures and admire creative artwork.                                    

Must-see if you are a first-time visitor:

  • Galena Historic District – This is the heart of Galena. I love taking a leisurely stroll down Main Street, where you’ll find charming 19th-century buildings housing boutiques, art galleries, and cozy cafés. It’s the perfect place to get a feel for the town's historic charm.
  • Blaum Bros. Distilling Co. – If you like whiskey, this is a must-see! I took the tour here and loved learning about the distillation process. The tasting room is a great spot to relax, and their locally crafted spirits are excellent.
  • Galena Cellars Winery – This place is just minutes from downtown, and it’s the ideal spot to unwind. I always enjoy a wine tasting here with a view of the vineyards. It’s a peaceful spot to sip some local wine and take in the scenery.

Where to Eat

  • Fried Green Tomatoes – This is my go-to for upscale American cuisine in Galena. The food is top-notch, and the restaurant itself is in a beautiful historic building. You can’t go wrong with their wine bar and Southern-inspired dishes.
  • Otto’s Place – If you’re in the mood for a cozy breakfast or brunch, this is the spot. Their creative coffee drinks and comfort food always hit the spot, and I love how relaxed the vibe is.
  • Log Cabin Steakhouse – Whenever I’m craving a hearty steak or seafood, this is the place to be. It’s a local favorite, and the cabin-style setting adds a rustic touch to the dining experience.

If you are interested in local events:

  • Galena Country Fair (October) – This is one of my favorite events. It takes place during the peak of fall foliage, and I love browsing the arts and crafts booths, listening to live music, and enjoying the food vendors. It’s a great way to immerse yourself in the local culture.
  • Night of the Luminaria (December) – The holiday lights here are truly magical. I’ve been a few times, and there’s something about seeing over 5,000 luminaries lining the streets and riverbanks that makes the night feel extra special.
  • Galena Balloon Race (June) – I had the chance to see the balloons take off one year, and it was an unforgettable experience. Whether you’re watching from the ground or riding in one of the balloons, this event is a must-see.

If you are looking for unique day trips within 30 Minutes of Galena, Illinois:

  • Dubuque, Iowa (30 min) – This nearby city has some great attractions, like the National Mississippi River Museum and the historic Fenelon Place Elevator. I love walking the Riverwalk along the Mississippi too.
  • Elizabeth, IL (15–20 min) – Elizabeth is a quiet little town with plenty of charm. I recommend checking out the Apple River Fort State Historic Site and the local antique shops.
  • Hanover Bluff Nature Preserve (25 min) – If you’re in the mood for a peaceful hike, this preserve has some great trails with panoramic views of the Mississippi River. I always find it so calming to walk here.
  • Chestnut Mountain Resort (20–25 min) – Whether it’s skiing in the winter or outdoor fun in the summer, I always enjoy a trip to Chestnut Mountain. The views are spectacular, and it’s a great spot for adventure.
  • Apple River Canyon State Park (30 min) – This is one of my favorite spots for some quiet nature time. You can fish, hike, or just enjoy the serenity of the canyons and bluffs.

Frequently Asked Questions:

Map:


In Summary...

(and if you want to revisit my photo journey)