Unique Activities in Galena, IL For Couples
Planning the ultimate couples getaway starts with finding the perfect destination – and what we often look for is a destination packed with things like charm, connection and just the right amount of indulgence. Galena checks every box. Not only are there plenty of unique things to do in Galena, IL for couples, but this charming, historic town is home to one of the top-rated Bed and Breakfasts in the entire country: Jail Hill Inn. Tucked into the northwest corner of the state, this small town delivers big on character and experiences.
Galena’s appeal lies in its blend of historic charm and modern-day fun. From exploring scenic hiking trails and touring historic sites to discovering tucked-away wineries and dining at cozy, chef-driven restaurants, there are endless things to do in Galena, IL for couples looking to make the most of their time together. The town’s appeal lies in its beautifully preserved 19th-century architecture, which creates a picture-perfect backdrop for your couple’s getaway. Add in a few unexpected twists—ghost tours, hot air balloon rides, or a charming afternoon with friendly goats—and you’ve got the perfect recipe for one of the most memorable romantic getaways in Illinois.
To truly elevate your weekend getaway in Illinois for couples, consider making Jail Hill Inn your home base. Perched above downtown Galena, this award-winning Galena Bed and Breakfast blends history, luxury, and personalized hospitality like no other. Each suite offers over 800 square feet of comfort, complete with spa-like bathrooms, fireplaces, king-sized beds, and thoughtful extras like champagne and local chocolates. After a gourmet three-course breakfast, you’ll be perfectly fueled to explore the many Galena attractions and Galena activities nearby—or simply stay in and enjoy a quiet afternoon together. Our Galena Bed and Breakfast is much more than a place to stay—it’s an experience all its own. Book your stay today!
Best Things to Do in Galena, IL For Couples
If you’re dreaming up a romantic escape somewhere in the Midwest, move Galena, Illinois to the top of your list. This historic town has long been a favorite for couples looking for a weekend getaway in Illinois, and it’s easy to see why. Wander through Galena’s beautifully preserved downtown, where 19th-century buildings house everything from local art galleries to cozy cafes and boutiques, or take breathtaking views of the Mississippi River Valley from local parks and trails.
The town of Galena hosts plenty of signature events throughout the year, with something for everyone: art lovers, history lovers, wine lovers, and gourmands. For couples who like to mix in a little adventure, there’s no shortage of options, including hiking, biking, ziplining, horseback riding, and more. There are plenty of off-the-beaten-path adventures and hidden treasures in Galena, too, that will help you dial into the authentic nature of this town and what makes it so enduring.
From hands-on workshops to leisurely experiences, there’s a wide range of things to do in Galena, IL for couples. Check out our curated list below, and get ready for the best couple’s getaway of the year!
- Let’s start with one of the most popular things to do in Galena, IL for couples: Shopping. Who doesn’t love browsing through boutiques packed with unique-to-Galena finds? Downtown Galena is filled with them. And if treasure hunting is more your style, there are plenty of places to go antiquing in Galena, too!
- The wine industry in Galena has been burgeoning for years, and we’re happy to say that Galena has quickly grown into an exciting wine-forward destination. Wine tasting is one of the most delicious things to do in Galena, IL for couples. We love sending guests out for a sun and music-filled afternoon at Galena Cellars Vineyard, but if you’re looking for a more accessible wine-tasting experience, there are tasting rooms in downtown Galena, too.
- Speaking of delicious things, plan for some fantastic meals during your couple’s getaways! Galena restaurants will surprise you – especially Innkeeper favorites like Fritz and Frites, Fried Green Tomatoes, and Little Tokyo. In nearby Dubuque, we also recommend Brazen Open Kitchen and Bar and Timmerman’s Supper Club.
- Are you looking for unique things to do in Galena, IL for couples? How about Goat Yoga? Or maybe Goat Treks? These goat-y experiences are all the rage in Galena, and every guest who’s taken our advice to participate has positively raved about the fun they had!
- There’s another lesser-known activity to enjoy in Galena—and it involves taking to the skies! Hop in a hot air balloon at sunrise and take flight over the stunning, rolling hills of Galena Country below. It’s a great place to pop the question or just to marvel at the beauty of the world around us. By the way, if you like hot air ballooning, don’t miss the Great Galena Balloon Race this June – it’s one of the biggest Galena events of the year!
- How about some adrenaline-packed adventures? If you’re looking for thrilling things to do in Galena, IL for couples, turn to our friends at Long Hollow Canopy Tours. They offer a range of experiences, including Canopy Tours on six zip lines and an Aerial Challenge Course with 32 unique elements.
- For something a little less adventurous but equally beautiful, head out for a walk or bike ride on the Galena River Trail. There are also plenty of local nature preserves, such as Horseshoe Mound Preserve, Casper Bluff Land and Water Preserve, and the Valley of Eden Bird Sanctuary.
- Don’t miss your chance to fully unwind and embrace the downtime. A signature massage in the comfort of our Bed and Breakfast is one of the all-time best things to do in Galena, IL for couples. Our brand-new massage room is on the ground floor of the Inn and is perfect for solo or couple’s massages.
- Want something off the beaten path? There are plenty of unusual things to do in Galena IL for couples, too. How about ghost tours of Galena’s haunted past? Join the Haunted Galena Tour Company or Amelia’s Ghost Tours and explore the spookier side of Galena after dark.
- There are also some fun local hidden garden tours worth taking, one of which offers a glimpse at Galena’s historic past. Explore the historic Belvedere Mansion, but don’t miss its magnificent gardens. Afterward, head on over to Linmar Gardens for their tour.
This list doesn’t even scratch the surface of the many unique things to do in Galena, IL for couples. Magic shows, kayaking adventures, trolley tours, Presidential history—and so much more—are waiting for you!
A Couple’s Getaway Worth Talking About
There are plenty of couple’s getaway destinations in the Midwest, but none with the same level of charm or hospitality as Galena. That’s especially true when you choose our top-rated Galena Bed and Breakfast as your elevated home away from home. Our B&B offers something truly special—an experience that feels both effortless and extraordinary. We’ve thought of everything so you can focus on what matters most: enjoying uninterrupted time with your favorite person.
What makes our Galena Bed and Breakfast unique? It stands out—not just because it’s perched on a quiet hill overlooking downtown Galena—but because it tells a story. This striking four-story brick building once served as the county jail. Today, it’s home to six spacious guest suites that strike a perfect balance between historic charm and modern luxury. Inside, you’ll find oversized king beds, spa-worthy bathrooms, mood lighting, and curated extras like chilled champagne and curated local chocolates waiting for you when you arrive.
Each suite is over 800 square feet, giving you the room to stretch out, relax, and settle into your Galena getaway. Want to set the vibe? Fire up your in-room Bluetooth speakers, flip on the gas fireplace, and sink into premium linens that feel tailor-made for lazy mornings. And with high-end amenities like Aveda bath products and oversized walk-in showers, you’ll feel pampered from start to finish.
Mornings begin with a house-made, three-course breakfast that changes daily. Each breakfast is packed with seasonal ingredients, including those from our very own gardens, with fresh flavors and creative twists on classics. After breakfast, you’ll be set to explore the best things to do in Galena, IL for couples. From wine tasting and scenic drives to hiking trails and hot air balloon rides, there’s no shortage of unforgettable Galena activities.
Regardless of what you do during the day, don’t miss our afternoon wine and appetizer service—local cheese and charcuterie, warm cookies straight from the oven, and a curated wine list that you’ll choose in advance. It’s the kind of indulgence that makes staying in feel like the best plan of all. If you’re ready to elevate your weekend getaway in Illinois for couples, consider emailing us to arrange custom add-ons, from fresh flowers to celebration cakes and other thoughtful surprises. See why we’re not just one of the top-rated Galena attractions—but one of the best couples retreats in the Midwest. Book your stay today!
