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Dana & Jesse

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Things To Do

The Grape Escape

The Grape Escape

242 North Main Street, Galena, IL 61036

A great spot for drinks and live music!

Fergedaboudit Vineyard & Winery

Fergedaboudit Vineyard & Winery

4595 West Speer Road, Hanover, IL 61041

Our go-to spot for anniversary celebrations—beautiful views, great wine, and delicious cheese boards!

Blaum Bros. Distilling Co.

Blaum Bros. Distilling Co.

9380 US Highway 20 West, Galena, IL 61036

Another must-visit for adult beverage lovers.

Shenandoah Riding Center

Shenandoah Riding Center

200 North Brodrecht Road, Galena, IL 61036

Great spot for a trail ride the whole family will love.

Gobbie's Sports Pub & Eatery

Gobbie's Sports Pub & Eatery

219 North Main Street, Galena, IL 61036

A perfect Saturday daytime hangout spot—great pizza, local beer on tap, and an awesome outdoor patio to sit back and relax.

Galena Taphouse

Galena Taphouse

215 Diagonal Street, Galena, IL 61036

Galena Tap House is one of our favorite spots for its cozy, intimate vibe and expertly crafted cocktails — perfect for relaxed nights out.

The Galena Brewing Company

The Galena Brewing Company

227 North Main Street, Galena, IL 61036

Galena Brewing Company truly does it all — delicious beer, tasty food, and our favorite spot for live music. We love the fun, upbeat atmosphere—it’s always buzzing with energy, especially on karaoke nights. If we’re lucky, you might even catch Jesse on the mic!

Poopsie's

Poopsie's

402 South Main Street, Galena, IL 61036

Poopsie’s is a fun, quirky little shop in downtown Galena with the best mix of gifts, games, art, and random things you didn’t know you needed. It’s one of those spots that’s just fun to wander through and always good for a laugh or a cute find.

Otto's Place

Otto's Place

100 Bouthillier Street, Galena, IL 61036

A great spot for a slow morning—good coffee, great breakfast, and a cozy vibe.

Charlie's Place Eatery

Charlie's Place Eatery

200 North Main Street, Galena, IL 61036

One of our favorite local spots we love for a good breakfast and an easy start to the day—nothing fancy, just friendly people and solid food that hits the spot.

North Golf Course and Pro Shop

North Golf Course and Pro Shop

400 Eagle Ridge Drive, Galena, IL 61036

One of the best spots to golf in Galena—beautiful views, peaceful fairways, and a great place to squeeze in 9 holes while you're in town for the weekend. 😏

For all the days along the way
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