LGBTQIA+ Getaway in Galena, Illinois

To kick off your first day in Galena, start with some “pick-me-ups” at Galena Bakehouse, a grab-and-go, gay-owned bakery on Main Street. Order a made-from-scratch egg white empanada or a slice of the quiche of the day along with a freshly-brewed cup of coffee or a seasonal latte. Eat as you stroll down Main Street, or in the spring and summer sit at one of the outdoor tables.

Described as “the helluva half mile,” and with more than 125 retail shops, your Main Street adventure begins at Poopsie's where the kid in you comes out to play. Shelves overflow with one-of-a-kind games, toys, and gifts that make you laugh out loud. The vibe is fun, and the finds are unexpected. 

Check out Galena Book and Paper and browse new and classic books, including a few LGBTQIA+ titles, note paper, cards and gifts for any occasion. Then, cross the street, and let the scents of Galena Apothecary pull you in—fresh, clean, and earthy. Find everything from lotions and candles to natural skincare, small-batch soaps, and handcrafted goods. 

Need to do a little clothes shopping? Just a block away, the queer-owned Neighborhood Trading Co. sells clothing, gifts, and accessories with a modern, creative edge. This LGBTQIA+ safe space is perfect for finding something one-of-a-kind.

If you’re into vintage, playful, and retro vibes, and all of the walking and shopping has your stomach growling for a meal, then lunch at Durty Gurt’s Burger Joynt is a must! While burgers are their specialty, there are plenty of other “handhelds” on the menu for you to choose from. Be sure to save room for dessert that awaits you on Main Street. The Great American Popcorn Co. is about a 2 block walk, which you might appreciate after a filling lunch. Home to over 50 flavors of popcorn made daily, try the garlic parmesan for a savory snack, or, if you’re looking for a sweet treat, take your pick of homemade fudge, candies, chocolates, ice cream, or some of each. 

Before you work your way back up Main Street, just across the street is Geoffrey’s River Bend Gallery and Gifts. The gallery showcases Geoffrey Mikol’s work, including matted prints and gifts using his images. It’s the closest thing to taking a piece of Galena home with you.

So, having explored some of Main Street, and with a full belly and your sweet tooth satisfied, it’s time to hop on a Galena Trolley for a narrated history tour of Galena. Purchase a ticket, a snack, and a bottle of water and get ready for an hour-long tour of the scenery and history of Galena. It’s a great overview of things to do and places to see that you may want to revisit. 

After the tour, head back to Main Street for a little refreshment. And what better place for that, than at Rootbeer Revelry. Find a spot at the “bar” for a flight of five different rootbeers for tasting. Or, if you’re feeling nostalgic, order a rootbeer float—the salted caramel and chocolate is a must try. It is straw-licking good.

Take one final stroll on Main Street before dinner to check out the Galena Spoon Co. Find everything you “wood” want or need for the kitchen. Choose from handcrafted wooden spoons and kitchen boards to gourmet fare while enjoying an in-store spoon-carving demonstration. Then, walk the one block to your dinner spot for the evening. Once a local pharmacy, Fried Green Tomatoes, a multi-level dining space, has some of the best seafood, steaks, and Italian dishes in Galena. Be sure to save room for dessert. Their tiramisu is classic. 

Cap off your evening with a visit to Miss Kitty’s Grape Escape, an LGBTQIA+ friendly bar where specialty martinis, wine, and craft beers are always on the menu. Enjoy live music every Thursday through Sunday along with your beverage of choice. 

The DeSoto House and Hotel in downtown Galena puts you right in the middle of all of the action. The oldest operating hotel in Illinois, it’s where Presidents Lincoln and Grant once stayed. It's also rumored to be haunted, adding a touch of mystery to your stay. 

If you’re more of a “breath in some fresh mountain air each morning,” kind of traveler, the Chestnut Mountain Resort sits high above the Mississippi River. It’s about a 15-20 minute drive into town, so plan to have a vehicle or use a rideshare service.

Get ready for a day of touring and exploring Galena’s historical past by first fueling up at Galena Roasters Coffee Shop, a small-batch specialty coffee roasting company. Choose from espresso drinks, brewed coffee, or a cold brew. Pair it with a breakfast sandwich, pastry, or try their one-of-a-find Booster Juice for an early morning energy jolt. 

After breakfast, make your way to the Galena & U.S. Grant Museum to explore exhibits on lead mining, steamboating, and the Civil War, all housed in a historic 1858 Italianate mansion. Examine artifacts, enjoy interactive displays, and marvel at a hologram of Ulysses S. Grant that seems to make history come alive as you learn about Galena’s storied past. While you’re there, purchase tickets to your next stop, the Old Blacksmith Shop to “watch the sparks fly.” See how tools and equipment from its 100-year history are still in use by working blacksmiths. Be sure to browse the gift shop for handcrafted items made on-site. And speaking of “old,” don’t miss the Dowling House. Built in 1826, it served as a trading post on the first floor, with living quarters above. Today, it operates as a historic house museum, with 30-minute guided tours from May to November. Get up close and personal with period artifacts and furnishings that give you a glimpse into early 19th-century living.

For an inside look at the life of the 18th President of the United States, take a tour of the Ulysses S Grant Home. Built in 1860 and gifted to Grant in 1865, the house has many original family furnishings along with its mid-19th-century decor. Guided daily tours begin every 15 minutes. Then, on your way back to town for lunch, stop by  The Old Market House, built in 1846 and restored in 1955. Originally used by vendors and shoppers, it now houses the Galena Welcome Center.

After lunch, head over to P.T. Murphy Magic Theater to enjoy what visitors call “the best show in town.” Experience a 65-minute magic show in an intimate 24-seat setting, perfect if you like a little mystery during your stay in Galena. 

Galena is known for its wineries, so before dinner, doing a wine tasting is a must. At the Massbach Ridge Winery Tasting Room, choose four estate-grown wines to sample from their selection of whites and reds. Your wines arrive in a “wine tree,” ready for sipping. Enjoy them at the bar or settle into a comfy chair to take your time with each pour. 

After finding your favorite new wine, head up the street to the DeSoto House Hotel for dinner, along with a little more history and some added mystery at the  Generals’ Restaurant. Located on the lower level of the hotel, it honors the nine Civil War generals with its historic setting of brick walls and beamed ceilings. Expect to hear stories of the "Lady in Black," a ghostly figure that lingers by the fireplace, adding a touch of intrigue to your meal. 

Did someone mention a ghostly figure? The Lady in Black is merely a preview of the haunting history you’ll discover as you end your day on the Haunted Galena Ghost Tour. Take a spine-tingling stroll through Galena’s shadowy past guided by storytellers in period costumes. Explore historic streets while unraveling tales of restless spirits, local legends, and eerie encounters. With every step, the line between history and hauntings blurs, keeping you both on edge and eager for more.

Have you spent enough time inside stores, restaurants, theaters, and historic buildings and feel a longing for the great outdoors? If so, Mother Nature is calling for you to experience all that Galena has to offer in outdoor adventures. But first, you need to fuel up. Kaladi's Coffee Bar is the perfect stop before heading out for a hike or exploring Galena’s outdoor attractions. Grab your coffee to go, or take a moment to plan your day of adventure. 

Then, head to Hoof It Goat Treks for a true one-of-a-kind experience. The trek takes you on a 1.25-mile hike through forests and prairies, with goats happily tagging along ready for hand-fed treats and fun photo moments. Lasting about 45 minutes, it’s all-ages friendly and, when all is said and done, we’re sure you’ll agree, it’s the G.O.A.T (Greatest of All Treks.)

Saddle up, partner as you move on to your next excursion. At the Shenandoah Riding Center, located just a few miles from downtown Galena, enjoy guided trail rides, riding lessons, lead line rides,and wagon rides. It doesn’t matter if you're an experienced rider or new to horseback riding, the center has experiences for all ages and skill levels. 

Head back into town for a grab-and-go lunch at Big Bill's Sandwich Shop and Coffee Bar located in the historic Logan House building. Order a sandwich piled high with your choice of roast beef, turkey, corned beef, or chicken salad. Pair it with a side of chips, and a beverage, and then make your way to Horseshoe Mound Preserve for a picnic lunch. Relax in the central gathering area, and take in panoramic views of the city and distant landscapes across three states. After lunch, explore the hiking trails that lead to scenic overlooks like the Spiroff Overlook. Look for the viewing scopes and educational plaques along the way to better understand the area's natural and geological significance.

For a different side of Galena’s history and charm, Linmar Gardens is a 3.5-acre oasis atop a limestone bluff. Once a lead mine and stone quarry, explore its winding paths, water features, and a sunken garden built within the ruins of one of Illinois' oldest African-American churches. Guided tours are available giving you insight into the garden's history and design.

Wrap up your Galena three-day getaway with dinner and a show at Amelia’s Under the Lamplight Dinner Theater. Located on Historic Main Street, this supper club is a unique dining experience with live entertainment. Enjoy a three-course meal while professional entertainers perform comedic and musical acts, murder mysteries and magic shows. Check their event calendar to see what’s “showing” while you’re in town.

Galena is a 10 out of 10 when it comes to LGBTQ+ friendliness. Add to that its small-town charm, history, iconic Main Street, parks, and gardens, and you have all the makings of a destination worth moving to the top of your travel bucket list.

Dive deeper into the LGBTQIA+ experiences in Galena with OutCoast

Originally written by Fay Stevenson of OutCoast