Downtown Galena is a wonderful place to spend a bit of time this summer!  The charming, historic Main Street is lined with incredible shops, restaurants, historic attractions, and more.  Our shop and restaurant owners have been working hard over the last year, too, to make the experience a safe and enjoyable one in the face of the COVID-19 pandemic.  That includes part of downtown Galena being closed down to cars to make room for outside dining, too!

Jail Hill Inn is just steps away from Main Street in downtown Galena, which means when you stay here, you’re at the heart of the action. You can shop ’til you drop, enjoy a delicious dinner for two, access the popular Galena River Trail, or even sample a bit of local wine and beer without hopping in your car!  It’s one of the many great things about staying at our Galena Bed and Breakfast.

Not only that, but you’ll find our sumptuous accommodations far exceed your expectations, with a gourmet breakfast and delicious wine and appetizer tray served fresh to you each and every day. This summer, come explore the fun and multi-faceted town of Galena with us!  We’re only a short drive away from major midwest cities like Chicago, and offer you an escape to an entirely different world.  What are you waiting for?  Book your room at our sensational Galena Bed and Breakfast today!

Enjoy the Best of Downtown Galena

There’s so much fun to be had in downtown Galena that it’s hard to capture it in a single blog post.  In part, exploring the different shops, restaurants, tasting rooms, and historic attractions in downtown Galena is what makes it an exciting place to visit time after time.  Whatever it is you do, we’re sure you’re going to enjoy the historic architecture and small-town charm. It’s what makes Galena, Galena after all!

We’ve compiled a list of some of our favorite features of downtown Galena, in hopes of giving you a clear picture of everything that awaits you in this charming getaway town.

Galena Restaurants

Given Galena’s small size, it might come as a surprise to you that there are some great dining options in downtown Galena.  Our small town is big on flavor, though.  Here are a few of our favorite Galena restaurants!

1. Fritz and Frites is the #1 rated Galena restaurant, and they are a charming little bistro that serves up a delicious combination of French and German specialties.
2. Fried Green Tomatoes, which is well known for its incredible steaks and its extensive wine list.
3. The Log Cabin Steakhouse is the oldest and longest-running restaurant in Galena.
4. Grab lunch at Big Bills Sandwich Shop and Coffee Bar.  They roast the coffee we serve at Jail Hill Inn, but they also offer some truly amazing sandwiches served on their freshly baked bread.
5. Though Brazen Open Kitchen and Bar isn’t technically in Galena (it’s in neighboring Dubuque), the chef and owner is a Galena native, and we like to support his business, too.
6. Frank O’Dowd’s Irish Pub & Grill is a happening place, and one of the best places to go to if you want live music and entertainment while you dine.
7. Head to Little Tokyo’s and enjoy authentic Japanese ambiance and a delicious range of high-quality sushi and sashimi.
8. If you’re in the mood for a burger, then you’ll want to head to Durty Gurts.
9. Imported deli items and good Italian food are what Vinny Vanucchi’s has in store for you.
10. The Market House Restaurant is one of the many hidden gems of Galena. This Galena restaurant is quaint, cozy, and the service is outstanding.

Shopping in Downtown Galena

There are more than 100 shops on this little stretch of Main Street, which was voted one of “America’s Best Main Streets” by Fodor’s Travel.  Among our favorite shops, you’ll find a wonderful collection of antiques and collectibles, perfect gifts for those you may be shopping for, and plenty of locally-made and gourmet goodies, including, of course, some local wine. Some of our favorite businesses (some of which are even featured at our Galena Bed and Breakfast!) include the following:

1. Galena River Wine & Cheese
2. Galena Spoons Co.
3. Galena Cellars or Massbach Ridge Winery, or Blaum Bros. Distilling.
4. Big Bills Sandwich Shop & Coffee Bar
5. Vignettes of Galena
6. Simply Elegant Home
7. The Towne Rebel
8. River Bend Gallery
9. Thomas Mangelsen Images of Nature Gallery
10. Galena Canning Company
11. Galena Garlic Company
12. Spice & Tea Merchants
13. Great American Popcorn Co.
14. Stam Chocolates
15. At Home in Galena
16. Galena Apothecary
17. Galena Candle and Bath Company

Historic Attractions

Most of Main Street in downtown Galena is itself a historic attraction. More than 85% of the buildings are on the National Register of Historic Places!  The fact that the towns 19th century architecture has been so well preserved is definitely one of the best things about this incredible place.  Get to know a bit of Galena’s history on a walking tour through downtown Galena, operated by the Galena History Museum.

You can also get to know a bit of downtown Galena’s history on a trolley tour of the town with Galena Trolley Depot.  There are a few tours to choose from, but by far the most popular is the hop-on/hop-off tour that navigates its way around Galena’s most popular historic attractions. For something really fun (and a bit different), take one of the haunted ghost tours of downtown Galena.

Relax and Unwind at our Galena Bed and Breakfast

We know that when it comes to choosing where to stay on vacation, location matters.  Our Galena Bed and Breakfast is situated perfectly to allow you to enjoy the best of downtown Galena. Our historic Bed and Breakfast is situated less than a block off Main Street and overlooks downtown Galena. Our location puts you within easy access to all of the best shopping, restaurants, and nightlife of downtown Galena.

While the location is important, it’s only part of the story here at our luxurious Galena Bed and Breakfast.  Jail Hill Inn is the only Inn in the country to be named in the top 10 of Inns 3 years in a row. We were the #1 B&B in the country in 2019, #3 in 2020, and now in 2021, we’re the #7 B&B. Being ranked so highly nationally is, of course, reflective of the experience you’ll enjoy at Jail Hill Inn.  We’ve thought of everything, and strive to make sure you are well taken care of from the start of your getaway through to the end.

Our guest suites are spacious and well-appointed, with luxury amenities you’d expect from a 5-star hotel chain. Each morning, we treat you to a delicious made-from-scratch breakfast that doesn’t disappoint.  You can either enjoy breakfast in the comfort and privacy of your suite, or you can join us for a more lively celebration in the dining room.  In the afternoon, relax and unwind from your adventures in downtown Galena with our impeccable wine and appetizer tray.  We custom-make appetizers in-house every day and have partnered with other local businesses like Galena Cellars and Galena River Wine and Cheese, to bring you a delicious and curated tray of goodies to enjoy.

Truly, we can’t wait to welcome you to downtown Galena and sharing the best of this incredible town with you.  Book your room at the #1 rated Galena Bed and Breakfast today!