319 Meeker St. Galena, IL 61036



Four Day Itinerary to Galena

Start your day with a sumptuous 3-course gourmet breakfast at Jail Hill Inn. From there, head down to Galena’s Historic Main Street is just 1 block away. As you head south on Main Street, take in the scope of Galena’s extraordinary range of shops, historic architecture, and friendly small-town charm. Galena’s Main Street, nicknamed the “Helluva Half Mile,” is filled with over 100 different shops and boutiques. Shopping and Dining along Main Street on Galena's Helluva Half MileSome of our guests’ favorite stores to visit include The Towne Rebel, The Galena Canning Company, Galena Candle and Bath, Vignettes, Simply Elegant, Elle & Becks, Isabella’s, Poopsies, River Bend Gallery, and Images of Nature Gallery.

At some point while browsing shops, you’ll be ready for a small bite to eat. Stop in for a light-lunch and great coffee at Big Bill’s Café. After lunch, take a trolley tour. This one-hour tour is a great way to learn all about the historic significance of Galena, as well as see many of the most important sites in town. When you’re done, grab a cocktail or glass of wine at Galena River Wine & Cheese, Jamie’s Wine Studio, or the Green Street Tavern. Be sure to also enjoy Jail Hill’s Wine and Appetizer hour, which starts at 5pm everyday in our lobby. It’s the perfect way to unwind after a day of shopping and sightseeing. Cap off your evening with a delicious dinner at Fried Green Tomatoes.

When you’re ready to leave the Inn for the day, head down the street and cross the Meeker Street Footbridge. It will take you directly to the Galena River Trail, where you can enjoy an easy, beautiful day hiking or biking. It’s a great way to work off your breakfast! The Galena River Trail follows the meandering Galena River, and extends for over 10 miles from downtown. Along the way, the trail passes Hiking and Biking along the Galena River Trail in Galena, IllinoisGalena’s historic Grant Park, the Train Depot, and plenty of beautiful wooded areas, farmlands, and bluffs. For an interesting side trip from the Galena River Trail, walk up Bouthillier Street and tour president U.S. Grant’s home, which is now owned by the State of Illinois.

After a day of hiking and exploring, come back to the Inn to relax on our third floor back deck, or main level patio. You can even schedule an in-room massage by one of our approved massage therapists; the perfect antidote to those tired muscles!  

After you’ve enjoyed a little bit of downtime, head to the Blaum Brother’s Distillery for their 3pm distillery tour. Here, you’ll learn about their craft bourbon, vodka, gin and whiskey, each made with ingredients sourced from this region. After the tour, come back to the Inn to enjoy our daily wine and appetizer hour, before heading out for a romantic dinner at Fritz & Frites

Fuel up for your day with Jail Hill Inn’s incredible 3-course breakfast; you’re going to need it! Next, head to Fever River Outfitters in Downtown Galena. Here, you have the choice between renting bicycles, canoes or kayaks, and even stand-up paddle-boards. From there, you’re free to spend the morning enjoying a leisure bike ride or Paddle down the Galena River in Galena, Illinoispaddle. If you’re here during the winter, this is the perfect day to check out Chestnut Mountain Resort. You can rent skis or snowboards, and enjoy picturesque views of the Mississippi River the entire time you’re hitting the slopes. If its your first time skiing, they also offer ski lessons from their highly trained instructors.

After your adventurous morning, grab a late lunch downtown at Durty Gurts. From there, work your way back to the Inn, stopping along the way at our Old Blacksmith Shop. It is an authentic 1897 blacksmith shop, complete with working forges and filled with tools and equipment over its 100 year history. Tours are available if you’re interested. Once you’re back at the Inn, enjoy our daily wine and cheese appetizer hour, and relax for the remainder of the evening, stepping out only for dinner at Log Cabin Steakhouse.

After your gourmet breakfast at the Inn, hop in your car and head out to explore some of the small towns in the surrounding countryside.  Ten miles east of Galena is Elizabeth, IL. Elizabeth is a great town for the antique lover, and is home to two popular antique stores: Common Cents and the Elizabeth Grand Antique Store.  Two additional historic sites in Elizabeth include The Blackhawk Fort and the Chicago Great Western Railroad Museum, both home to excellent exhibits worth Exploring the Greater Galena Areachecking out.

Grab a late lunch and fantastic cup of coffee at E-Town Cafe in Elizabeth before heading north for more adventure.  Your next stop will be in Schapville, IL. Here, check out “A Bushel and a Peck” country store, which houses a great collection of antique, vintage, reclaimed, and  re-purposed home furnishing and decor. From there, continue on to the quaint town of Scales Mound, IL. Ninety percent of the town is on the National Register of Historic Places.

If you need a nature break, enjoy some great hiking northeast of here near the Wisconsin border, at the Apple River Canyon State Park. This area is captivating, with it’s limestone bluffs, deep ravines, springs, streams, and wildlife.

You’ve seen so much during your time in Galena. Come back to the Inn one final time, and enjoy relaxing during our afternoon wine and appetizer hour. This is a great night to grab some takeout or order in at the Inn! Cannovas Pizza and Procentos Pizzeria are both great options.

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