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The Best of the Best in Galena

Our Favorite Things to do in Downtown Galena for 2023

Jail Hill Inn, the premier Bed and Breakfast in Galena, is situated at the edge of downtown Galena, which just so happens to be the second most visited tourist destination in Illinois, behind only Chicago. For a town of such a small population, that’s an impressive feat! But one visit to downtown Galena, and we think you’ll immediately see why it’s become – and stayed – such a popular getaway destination. 

Main Street in downtown Galena is only about 1/2 mile long, so it might surprise you that there are quite a few things to do in downtown Galena. But with some truly unique and fantastic shopping, plenty of great Galena restaurants, wine-tasting rooms, and a series of fun events throughout the year, Galena really does put on a show for all who visit. That’s just as true in the winter as in summer, too! 

Whether you have only one trip planned to enjoy the very best things to do in downtown Galena this year or you plan to make repeat trips to this charming, historic destination, the best place to stay in downtown Galena is the Jail Hill Inn. Our Bed and Breakfast in Galena is the area’s only luxury property of its kind. We’re the sole lodging property outside of Chicago to have earned four-diamond status with AAA, and we’re also a Select Registry member. We have been named the #1 and #2 Bed and Breakfast in the country by TripAdvisor.

With only six guest rooms on offer, we also offer an incomparable getaway experience for couples looking for a memorable getaway. Book your room at our Galena Bed and Breakfast today!

The trolley tour is a great way to enjoy the historic attractions in downtown Galena

The Best Things to do in Downtown Galena in 2023

With so many great things to do in downtown Galena, you really can choose your adventure for the day. History lovers will love to do things like take a trolley tour or visit the most popular historic attractions; shoppers will delight in wandering up and down Main Street hopping from one shop to the next; and wine lovers will enjoy visiting tasting rooms in downtown Galena and visiting wineries around town, too.

There really is something here for everyone, and that, aside from the naturally beautiful backdrop of this historic town, keeps downtown Galena ranking as one of the best small towns in Illinois worth visiting. The best part about this is that all this and more is at your fingertips when you stay with us at our top-rated Bed and Breakfast in Galena. Main Street and the best of downtown Galena are just steps from our front door – but at the same time, it feels far enough removed that when you retreat to the cozy luxury of our guest rooms, you’ll be far away from the hustle and bustle of restaurants and shops.

Below, we’ve listed a few of our favorite ways to spend time in downtown Galena and highlighted our favorite attractions in each category.

History Lovers

History lovers absolutely adore downtown Galena. Much of the entire town is on the National Registry of Historic Places, and their 18th-century facades are fun to admire as you stroll throughout town. Here are a few of our favorite things for history lovers to do in downtown Galena.

  1. Get to know a bit of Galena’s history via a walking tour through downtown Galena. Plan in approximately one hour for this tour.
  2. If you don’t want to walk, ride the trolley! Galena’s Trolley Tour is a hop-on/hop-off tour that navigates around Galena’s most popular historic attractions.
  3. Visit the U.S. Grant Home, the former residence of Galena’s most famous resident, former president U.S. Grant. The house was thoroughly restored in 1955 and still contains many original furnishings.
  4. Another great historic attraction in downtown Galena is the Belvedere Mansion, built in 1857 and considered the finest home of its kind in the Galena area. The house and its stunning gardens are open to the public from May – November and beautifully showcase what life was like for one of Galena’s wealthiest residents.
  5. The Dowling House is one of Galena’s oldest homes, constructed around 1826-27. The house was built of Limestone and was, at one point, the only trading post in the city.
  6. If you’re interested in Galena’s haunted history, try a ghost tour with Amelia’s Ghost Tours or The Haunted Galena Tour Company.

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 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

Wineries, Breweries, & Spirits

Downtown Galena is also fortunate enough to be home to some excellent wineries, a brewery, and a distillery, not to mention a great collection of bars. Below are some great options for a casual drink while in Galena. 

  1. Galena Cellars is the most popular winery in the area, and they have a tasting room in downtown Galena. 
  2. Massbach Ridge Winery also has a wonderful tasting room in downtown Galena. 
  3. For some bubbly-themed fun, don’t miss Champagne on Main
  4. If you prefer a pint of beer, we can’t recommend the Galena Brewing Company enough. 
  5. For delicious cocktails, it’s worth the (very) short drive out of downtown Galena to Blaum Bros. Distilling, where you can tour their distillery, sample their spirits, and enjoy some delicious hand-crafted cocktails. 
two women enjoying drinks on the patio at Jail Hill Inn, the best place to stay in Downtown Galena

The Best Place to Stay in Downtown Galena

Though there are plenty of lodging options near downtown Galena, one place stands out above the rest as the best place to stay in downtown Galena, and that is our luxury Bed and Breakfast in Galena. Whatever brings you to this historic town, we think the relaxed elegance of our Inn and the unparalleled hospitality you’ll enjoy once you’re here will keep you coming back for multiple getaways. 

Our Bed and Breakfast prides itself on attention to detail. You’ll see and feel that difference from the moment you first arrive. Once you’ve been checked in and shown to your room, you’ll find a bottle of chilled champagne and custom chocolates waiting for you. Shortly after that, you’ll be treated to our daily wine and appetizer hour – a treat that continues every afternoon of your stay! 

As you get settled into your suite, take the time to get acquainted with its features, ranging from customizable Bluetooth sound systems to luxury jetted tubs and/or steam showers. You’ll soon see that these accommodations are anything but ordinary, and it’s all just part of what makes us one of the best places to stay in downtown Galena!  

We’ll treat you to a freshly prepared breakfast with our signature dishes in the morning. The menu changes daily and with the seasons, but it always includes a delicious fruit-based start, followed by a pastry, a delicious main course, and freshly roasted coffee and juices. 

For uncompromising luxury, the next time you visit downtown Galena, make sure to book your stay at the best of the best in downtown Galena, our Bed and Breakfast in Galena! 

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