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The Best of the Best in Galena

Galena is One of the Best Small Towns in Illinois

Best Small Towns in Illinois

It’s that time of year when we’re all ready for a relaxing getaway: summer vacation has begun, and the sun is shining. Thankfully, Galena is one of the best small towns in Illinois to do just that. The charming downtown main street is lined with quaint, locally-owned shops, cafes, and restaurants. You’ll see history in every brick and cobblestone, transporting you away from the hustle and bustle of everyday life.

Of course, your lodging choice becomes the most crucial factor for a getaway focused on romance and relaxation. Galena happens to be home to one of the most luxurious bed and breakfasts in our region: Jail Hill Inn. In fact, for the past four years in a row, we’ve been in the top ten of best bed and breakfasts in the US on TripAdvisor—holding the number one spot in 2019 and the number three in 2020. Every single one of our 550+ reviews is rated five stars, and not many lodging properties can make that claim.

Galena is one of the best small towns in Illinois due to renovated properties like Jail Hill. The old Jo Daviess County Jail sat abandoned for generations, and thanks to Matthew Carroll—Galena native, Innkeeper, and Owner—this beautiful building has a second chance. Meticulously renovated and designed, the Inn has six spacious suites, all with luxurious Kohler bathrooms, king beds, cozy seating areas, and callbacks to the original architectural details of the ancient jailhouse.

Join us in one of the best small towns in Illinois and book your next getaway today!

Best Small Towns in Illinois

Galena is one of the Best Small Towns in Illinois

There are so many great things to do in Galena, the majority of which are within just a quick five-minute walk from our Illinois bed and breakfast.

Check out these things to do in Galena—one of the best small towns in Illinois:

  • Shopping on Main Street: You’ll want to head to the charming downtown stores more than once during your stay. For your first stroll, window shop to take in all your options. There’s something for everyone: women’s apparel, gifts, jewelry, wine, candy, and popcorn shops. Be sure to pop into Galena Canning Company for a staggering collection of hot sauce, pickles, canned goods, and more.
  • Galena River Trail: The best small towns in Illinois are walkable, and you’ll find the Galena River Trail is the perfect way to start your day. The well-maintained and wide path is peaceful and quiet, except for the charming birds chirping as you take in the scenery.
  • Best Galena Restaurants: Dining out is an essential part of any getaway, and we have some fantastic restaurants in downtown Galena. Head to Bread and Vine for a Parisian-style pastry or sandwich, perfect for a late lunch or early dinner. Fried Green Tomatoes serves Italian fare with fresh ingredients and hospitality. Be sure to check out Frits & Frites, another longtime favorite for locals and visitors alike.
  • Wine and Beer Tasting: Relaxation is often paired with a fine glass of wine or a refreshing pint of beer, and Galena is one of the best small towns in Illinois for an adult beverage. You’ll find the three-floored Galena Cellars for a lovely wine tasting experience and Galena Brewing Company for locally brewed ales.
  • Take a Distillery Tour: About a ten-minute drive from downtown, Blaum Bros. Distilling Company is an excellent place for a tour, spirits tasting, or a fancy cocktail in their leather couch-adorned lounge. They are opening an outpost in downtown Galena, coming soon!

Best Small Towns in Illinois

The Ideal Lodging Choice for your Next Getaway

For those genuinely searching for the best small town in Illinois to explore, Galena is the ideal choice. Not only are we located an easy and scenic two-hour drive from Chicago, but once you’re here, everything is within walking distance from our luxury Bed and Breakfast. There’s ample free parking and an EV charging station—and it’s just a quick three-minute walk to all the fantastic activities downtown.

At the Inn, we take care of breakfast with a gourmet three-course meal with fruit, baked, and savory entree course. You’ll enjoy dishes like a caramelized poached pear, freshly baked fruit danishes, and flavorful quiche with twisted bacon (a house specialty.) It’s the best way to start the day before exploring one of the best small towns in Illinois! Book your stay today! 

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