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The Best of the Best in Galena

Downtown Galena IL is the Perfect Place to go Shopping

Galena, Illinois, is the kind of place where you can slow down and enjoy the simple pleasures of a historic small town with a lively personality. Start your day by wandering along Main Street, where beautifully preserved 19th-century buildings house unique boutiques, antique shops, and locally owned specialty stores. Galena, IL shopping is one of our favorite ways to soak up the many charms of this special place. Whether you’re hunting for home decor, handcrafted jewelry, antiques, or gourmet treats, shops in Galena, IL, are positively a delight.

Of course, shopping is just one of the many things to do in downtown Galena. After a morning of browsing the best Galena, IL shops, stop in at one of the town’s cozy cafés for a pick-me-up before heading to one of the area’s wineries to sample locally made reds, whites, and rosés. If craft beer is more your style, Galena also has excellent breweries where you can sip a flight of seasonal ales. Beyond shopping, there’s no shortage of ways to enjoy Galena’s scenic surroundings.

History lovers can explore the Ulysses S. Grant Home State Historic Site or tour the Belvedere Mansion for a glimpse into the town’s past. Outdoor enthusiasts can hit the trails at Casper Bluff Land & Water Reserve for sweeping views of the Mississippi River or try a guided kayak trip on the water. If you’re visiting in the winter, Chestnut Mountain Resort offers skiing and snowboarding with some of the best views in the region. No matter the season, a leisurely drive through the rolling hills of Jo Daviess County is always a good idea, with plenty of charming farmsteads, wineries, and scenic overlooks along the way.

After a full day of exploring the best of downtown Galena, settle in for a comfortable stay at Jail Hill Inn, Galena’s top-rated bed and breakfast. Housed in a beautifully restored 19th-century building, this award-winning inn offers spacious, luxurious suites near downtown Galena. Guests can unwind with complimentary wine and cheese in the afternoon and wake up to a gourmet breakfast before another day of discovering Galena. With its prime location, thoughtful hospitality, and elegant accommodations, Jail Hill Inn is the perfect home base for a memorable getaway in one of Illinois’ most charming towns.
Book your room at the Jail Hill Inn, Galena’s #1 Bed and Breakfast, today!

Specialty gifts - a store you'll find in downtown Galena shopping

Head Downtown: The Best Shopping in Galena, IL

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 Galena shops, you’ll find a wonderful collection of antiques at places like the Galena Antique Mall, not to mention plenty of other collectibles, perfect gifts for those you may be shopping for, and plenty of locally-made and gourmet goodies.

Some of our favorite spots to hit up for the best Galena, IL shopping (some of which are even featured at our Bed and Breakfast in Galena) include the following:

  1. Galena River Wine & Cheese – they help to supply our wine and appetizer trays with daily charcuterie.
  2. Galena Spoons Co. – they crafted the magnificent trays our custom wine and appetizers are served on.
  3. Big Bills Sandwich Shop & Coffee Bar – they supply the daily coffee roast we serve at our Bed and Breakfast in Galena.
  4. Vignettes of Galena – Many of the beautiful home decor items at our Bed and Breakfast in Galena were purchased here.
  5. Simply Elegant Home
  6. The Towne Rebel
  7. River Bend Gallery – some of the beautiful photography of owner/photographer Jeffrey Mikol is featured at our Inn.
  8. Galena Canning Company
  9. Galena Garlic Company
  10. Spice & Tea Merchants
  11. Great American Popcorn Co. – they serve a tempting array of popcorn, which we sometimes feature at our Bed and Breakfast in Galena.
  12. Stam Chocolates – they supply us with custom-made chocolates that await every guest at our Bed and Breakfast in Galena.
  13. At Home in Galena
  14. Galena Apothecary – we purchase some of the fragrances found at our Bed and Breakfast in Galena here.
  15. Galena Candle and Bath Company

Galena, IL shopping is a special experience. The town has a lot to offer, and better yet, it’s easy to get to. To get from cities like Milwaukee, Des Moises, Minneapolis, St. Paul, and Chicago to Galena, all you need is a car and a tank of gas. Even though it’s so close to these major cities, driving into Galena will have you feeling like you’ve stepped back in time to another world. It won’t take you long to see why Galena consistently ranks as a top Midwest getaway destination, either.

Just like the Magnificent Mile, Downtown Galena’s Main Street is filled with all the best shopping, dining, and entertainment. It’s just steps from our Bed and Breakfast, too. In total, there are more than 125 Galena, IL shops and restaurants. Browse these beautiful and historic storefronts, and you’ll find local treasures ranging from candy and ice cream shops, spas, and boutiques to great restaurants, bars, and wine-tasting rooms. You won’t find bland chain stores here.  Instead, you’ll find a hard-working, independent spirit that is undeniably charming.

Just as the storefronts are charming, the restaurants are delicious. It might come as a surprise in such a small town, but Galena restaurants are diverse and inspiring. From the classic French fare at Fritz and Frites and the extensive wine list at Fried Green Tomatoes to casual Italian at Vinny Vanucchi’s, there’s something to please every palate.

We aren’t far from Dubuque, Iowa either, which is home to a wonderful array of restaurants like Brazen Open Kitchen and Bar (the chef and owner is a local Galena resident) and Timmerman’s Supper Club, offering you a delightful midwest Supper Club experience. These restaurants, like the rest of the businesses in downtown Galena and across the country, and going to need your support more than ever as we work towards economic recovery.

Exterior of the best Galena Bed and Breakfast near Downtown Galena

Stay at the Best Galena Bed and Breakfast

While you’re supporting Downtown Galena, we hope you’ll take the time to support us by staying at the Jail Hill Inn as well. One of the most important parts of any great getaway is the lodging you choose. You won’t find anything better than our Galena Bed and Breakfast. At Jail Hill Inn, we pay attention to even the smallest of details and enjoy every second of our time with each of our guests.

We offer 6 luxuriously appointed guest suites, each encompassing a space of 800 square feet that will far exceed your expectations. We’ve added luxury touches to everything we do at Jail Hill Inn, which includes our standard and value-added amenities.

This includes things like plush and custom-designed Frette Spa Robes, Aveda personal care products, custom bath salts, Frette towels, Kohler bubble massage tubs, steam showers, customizable Bluetooth sound systems in each suite, a delicious wine and appetizer hour each afternoon, fresh desserts every night, and so much more.

Our Galena Bed and Breakfast has received more than 400 reviews on TripAdvisor, and every single one of them has been a 5-star review.  Add to this 98% of our 150+ Google Reviews.  We don’t often like to toot our own horn, but we do love it when our guests do this for us.  These 550+ guests can’t be wrong, but perhaps it’s time you see it for yourself?

Our Galena Bed and Breakfast, and the town of Galena itself, is an unforgettable destination.  We hope to see your smiling faces supporting all of the wonderful small businesses that call this charming one-tank getaway-town home.  When the time is right, book your room at the Jail Hill  Inn for the getaway of a lifetime.

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Give your loved one a very special gift of a stay at Jail Hill Inn .  We offer gift certificates in many amounts.