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The Best of the Best in Galena

The Best Things to See & Do in Galena This Summer

There’s a reason Galena is the second most visited tourist destination in Illinois, behind only the major metropolis of Chicago. Galena is about three hours west of Chicago and offers a completely different experience – one that couples and solo travelers have been seeking for years. There’s a surprising array of things to do in Galena, IL, of course, but what draws in most visitors is the historic, small-town charm and the slower pace, all of which work in concert to set the stage for a relaxing getaway. 

Getaways here aren’t all about the things you can do in Galena, though. They’re also about relaxation and connection. For the ultimate getaway destination, we encourage you to stay with us at our top-rated Bed and Breakfast in Galena. We’ve been rated as the #1 Bed and Breakfast in the country, which means you can expect to find a luxurious experience here that simply can’t be matched by any other lodging in town. We’re also the only AAA four-diamond property outside of Chicago.

Our Inn is perched on a hill overlooking downtown Galena and the beautiful rolling hills of Galena Country. We’re close enough to Main Street for you to enjoy all the shopping, dining, and other things to do in Galena, IL, but far enough away for you to escape the crowds when you want to. From fantastic shopping and exceptional historic attractions to delicious wine tasting and beautiful hikes through the countryside, this little town has everything you want in a getaway destination.

We’d love to help you enjoy all the best things that Galena has to offer visitors – but first, let us treat you to the getaway of a lifetime. With more than 600 all five-star reviews, you can expect a getaway filled with exceptional, detail-oriented hospitality. It’s what sets our Bed and breakfast apart from the rest. Book your Galena getaway today! 

The historic trolley is one of the best things to do in Galena, Illinois for history lovers!

The Best Things to Do in Galena, Illinois

Upon check-in, guests – particularly those new to Galena – often ask us what there is to do in town. The answer to that, of course, depends on what it is you like to do during getaways! We’re lucky in that Galena is positively packed with a fantastic range of things to do. It’s this diversity of things to do in Galena, Illinois, actually, that makes it such a natural tourist destination – and it’s one of the things we love most about living here, apart from the friendly, small-town charm, of course. 

Whether you love tasting new releases of wine, beer, or spirits or would prefer to work off your breakfast calories by doing something active during the day, you’ll find no shortage of great things to do in Galena, IL. It really does offer something for everyone and has been awarded for being one of the best small towns in America. We wouldn’t blame you if you spent your entire weekend letting us pamper you with indulgent breakfasts, massages, and the many luxuries of our guest rooms. But when you decide to venture out for the day, below is a list of some of the fantastic things waiting for you in Galena.  

  1. If you do nothing else in Galena than browse the shops along Main Street in downtown Galena, it will have been time well spent. Perusing the unique shops downtown is one of the most popular things to do in Galena, Illinois. Main Street is filled with 100+ unique shops – no chain stores here!
  2. A vast majority of downtown Galena’s buildings are on the National Register of Historic Places, so don’t miss the chance to learn more about Galena’s history. A Great way to do this is by taking one of the Galena Trolley Tours
  3. Speaking of history, don’t miss the chance to tour the U.S. Grant Home, The Dowling House, or the Belvedere Mansion – and all the other exquisite historic attractions in Galena
  4. Are you in the mood for a little wine tasting? It’s increasingly becoming one of the most popular things to do in Galena, IL, and you have plenty of options at your fingertips. In town, you can go tasting at Galena Cellars WineryMassbach Ridge WineryJamie’s Wine StudioThe Grape Escape, and Champagne on Main. Others in the area include Rocky Waters Winery and Fergedaboutit Winery.
  5. The wine here is great, but you should also sample local brews at Galena Brewing Company and the spirits at Blaum Bros Distilling
  6. If you want to get outside and enjoy a breath of fresh air, there are plenty of outdoorsy things to do in Galena, too! From biking the Galena River Trail to paddling on the Galena River itself, our town is anything but boring!
  7. For something truly unusual but fantastic, take a goat walk with Hoof It Galena. It’s a two-for-one experience, combining a little animal therapy with an invigorating day in nature!
  8. There are some beautiful parks to visit in the area, too, including Mississippi Palisades State ParkApple Canyon River State ParkHorseshoe Mound Preserve, and one of the other incredible Jo Daviess County Conservation properties.
  9. Grab some picnic supplies and enjoy a beautiful afternoon at Thunder Bay Falls – a spillway waterfall that comes off Lake Galena. It’s easy to access and visible just off the main road. 
  10. During the winter, Chestnut Mountain Resort is a great place to enjoy some skiing. But during the summer, it offers a whole variety of new things to do, including a zipline, an alpine slide, and a gorgeous boat ride along the Mississippi River. 
  11. There are plenty of fun events to attend in Galena throughout the year. Some of our guests come back every year for them! Popular events include the Great Galena Balloon Race, Corkless in Galena, the Independence Day Celebration, Oktoberfest, the annual Halloween Parade, Holiday Fire in the Sky, Night of the Luminaria & Living Windows, and so much more. 
  12. There are a surprising number of golf courses nearby—ten to be exact! Top golf courses near Galena include Eagle Ridge Resort & Spa, the Galena Golf ClubWoodbine Bend Golf Course, and the Lacoma Golf Course.
Friends enjoying a glass of wine at our Bed and Breakfast - one of the top things to do in Galena, Illinois!

Stay at the Best Bed and Breakfast in Galena, IL

Whether you pick just one thing from this list or spend your vacation checking off this entire list of things to do in Galena, Illinois, we have little doubt that you’ll enjoy a memorable getaway in this charmingly historic town. That is especially true when you choose our Bed and Breakfast in Galena as your home base. Jail Hill Inn is an experience unto itself, with amenities and hospitality unmatched by other Galena lodging properties. 

Guests who stay at our Bed and Breakfast in Galena often turn into loyal guests, coming back time and time again and often earning themselves Repeat Offender status and free night stays. Though our guests enjoy plenty of luxuries and high-value amenities, like a daily breakfast, an afternoon wine and appetizer tray, luxury linens and robes, and so much more – what guests really come to us for is our detail and service-oriented hospitality. 

When you stay with us, you become a part of our family—and perhaps more importantly, a part of our history. We’re proud to be stewards of this historically preserved building and to share our little slice of Galena’s history with all the guests who cross our threshold. We’ll happily share our favorite things to do in Galena, IL, with you, and we’d love to hear about yours, too. If you want to join the Jail Hill Inn family and experience one of the Midwest’s most luxurious and coveted properties, it’s time to book your room at our #1 rated Bed and Breakfast in Galena!

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