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Experience the Best of Downtown Galena This Fall

Experience the Best of Fall in Illinois!

A beautiful fall view of Downtown Galena from Grant Park

Galena is one of the most beautiful small towns in the country - and even though we don't think it needs much improvement, it really wears its glorious fall colors well! If you're looking for a charming and romantic place to unplug and spend some time with your sweetheart this fall,  Galena is it!

There are plenty of things to do in Galena, but shopping, tasting, and exploring your way through charming Galena are definitely at the top of the list. There are more than 125 individually owned shops in this short 1/2-mile stretch of Galena, not to mention several restaurants, wine tasting rooms, bakeries, coffee shops, and more. 

A stroll through Galena is also an incredible journey through time. The town is filled with historic 19th-century buildings, most of which are on the National Register of Historic Places. When you've exhausted the streets of 

 Galena, you'll find even more great things to do in Galena's outskirts - including wine tasting, hiking, boating, biking, skiing in the winter, and so much more. 

This fall, let the friendly people of Galena charm you, and let the Select Registry Bed and Breakfasts in Galena treat you to the pampered getaway you deserve. There are three great Galena Bed and Breakfasts here, all of which offer a unique experience with upscale accommodations and exquisite hospitality. Even if you come as a stranger, you'll leave a part of the Select Registry family. Book one of these incredible Galena Bed and Breakfasts today! 

Beautiful architecture in downtown Galena

A Day in Beautiful Galena

One of the best things about Galena is how easy it is to get here - not to mention how easy it is to relax once you're here. Galena is considered a "one-tank" trip from some of the Midwest's biggest cities, like Chicago, yet it feels like you're a million miles away.

Whether you're into shopping, browsing local art, or wine (or other) tastings, Galena is a great place to spend a day or two. So many incredible shops and businesses are packed into this charming and historic 1/2-mile stretch of road - it's really impressive! Galena is also absolutely gorgeous. 

Downtown Galena hugs the banks of the Galena River, and though you can walk from one end to the other in just a few minutes, we think you'll be blown away by how much this sweet little town has to offer visitors. Here are some top things to do & places to visit in Galena this fall.

  1. Shop 'til you drop!  It's one of the most popular things to do in Galena - where you never know what hidden treasures you might find!
  2. Don't miss the magnificent art galleries in Galena. There are some fantastic local artists here, including Geoffrey at River Bend Gallery, Outside the Lines Gallery, Skidmore Gallery, and the Carl Johnson Gallery.  
  3. Visit one or more of Galena's fantastic bakeries or coffee shops.  Popular choices include Bread and Vine, the Galena Bakehouse, and Big Bills Sandwich Bar & Coffee Shop.
  4. Do a little wine tasting in Galena at Galena Cellars or Massbach Ridge Winery
  5. There are some other great tastings you don't want to miss in Galena, too, including Galena River Wine and Cheese and the Great American Popcorn Company
  6. Speaking of yummy things, Galena also has some great restaurants. Popular local favorites include Fried Green Tomatoes, Fritz and Frites, Bread and Vine, and Little Tokyo
  7. Get oriented to Galena's fascinating history on the Galena Trolley Tours.
  8. Don't miss the chance to walk across the Galena Pedestrian Bridge over the Galena River. It will take you to Grant Park, where you'll find one of the best views of Galena. 
Harvest grapes at local Galena wineries and Vineyards - one of the best things to do in Galena outside of exploring downtown Galena

More Things to do in Galena This Fall

Galena is truly a magnificent getaway destination and a great place to relax with your sweetheart.  There also happens to be plenty of wonderful and fun things to do in Galena, IL.  Guests have been known to visit this town time and time again because it's beautiful and because there are so many things to do in Galena to keep you busy and having fun. 

While enjoying the best of downtown Galena this fall, we hope you join us in exploring all the other fun things to do in Galena, too. Below are just a few of our favorite things to do in Galena, especially when the magical beauty of fall unfolds. 

  1. Don't miss your chance to learn more about the history of beautiful Galena. Visit the town's most popular historic attractions, like the U.S. Grant Home, the Dowling House, and the Belvedere Mansion
  2. Speaking of history, you can experience it in a unique way if you take one of the town's ghost tours! It's one of the most exciting things to do in Galena each fall. 
  3. Don't miss your chance to visit the top GAlena wineries. Sipping and swirling your way through the countryside is one of the most popular things to do in Galena. Though you can find tasting rooms in downtown Galena, we also love heading out to the countryside. Places to visit include Galena Cellars, Massbach Ridge Winery, Rocky Waters Winery, and Fergedaboutit Winery.  Other don't-miss tastings include Blaum Bros Distilling and the Galena Brewing Co.
  4. Head to Chestnut Mountain Resort, which offers some of the best views of the Mississippi River. It's a great place to ski in the winter, but it provides breathtaking chair lift rides in fall.
  5. Enjoy even more beautiful views of the Mississippi River at Mississippi Palisades State Park. It's lovely in the fall and is also a spectacular destination for bird watching. 
  6. Bike or walk portions of the Galena River Trail. It's one of the most popular things to do in Galena, IL, and offers excellent views over the city. 
  7. There are plenty of places to enjoy hiking through the scenic rolling hills of the Galena area, including Horseshoe Mound Preserve, which offers a beautiful 3-state view on a clear day. 
  8. Get up close and personal with Galena's fall foliage with Long Hollow Canopy Tours. These ziplines are one of the most popular things to do in Galena in the fall. 

As great as these things are, it goes without saying that one of the best things to do in Galena this fall is to relax, unwind, and enjoy a bit of pampering at one of the Select Registry groups Galena Bed and Breakfasts. There is simply no better place to stay in Galena. Book your getaway this fall to experience the magic of Galena for yourself!

Best Places to Stay Near Galena

Jail Hill Inn

Jail Hill Inn is a boutique Galena Bed and Breakfast inn located one block from downtown historic Galena Illinois, prominently situated to overlook Galena and its stunning countryside. Choose from 6 different, 800-square-foot, luxury suites for your perfect getaway.

When you stay at Jail Hill Inn in Galena, you will enjoy a wonderful reception of wine and cheese on your arrival, and in your suite chocolates and chilled champagne awaits you. After a great night's rest, you will enjoy a 3-course, gourmet breakfast in our 1st-floor dining room.

We also have the unique distinction of being the only converted jail out of the 350 Select Registry properties. The 135-year-old, 4-story brick building that served as the county jail for nearly 100 years was completely renovated in 2015 with amenities that will thrill any traveler. With 45 windows (some 9 feet tall), 14-foot tall, curved brick ceilings, original 4th-floor beams, and unique vaulted ceilings, the history and architectural detail in the building are significant. 

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Goldmoor Inn and Resort

Located on a bluff with sweeping views of the Mississippi River, Galena’s historic Goldmoor Inn provides a romantic, and cozy four star luxury retreat with 13 uniquely decorated suites, three cottages and two log cabins.

Each of the 18 accommodations offers an in room whirlpool, private fireplace, private in-room gourmet breakfast and many other distinct amenities to pamper you during your stay.

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Best Places to Stay in Galena

aerial fall
tree changing color
guest room with fireplace
grand hall
Goldmoor Exterior at Dusk
winter Goldmoor
log cabin
guest room with fireplace
side door

Goldmoor Inn and Resort

Galena, IL

Jail Hill Inn- interior shot
Jail Hill Exterior 29
Jail Hill Inn- interior shot
Jail Hill Inn- cheese and wine
Jail Hill Room 6
Jail Hill Inn Exterior
delicious jaill hill in yogurt cup and french press coffee and tasty pastries
Jail Hill Inn- guestroom

Jail Hill Inn

Galena, IL

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