Galena Getaway

Enjoy a romantic getaway to Galena. Experience a charming historic town with shopping boutiques, cozy bed and breakfasts and a thrilling balloon festival.

in Regional Getaways
January 01, 2016

The picturesque houses of historic Galena in Illinois.

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Soar to new heights in a charming river town.

Nestled near the Mississippi River in northwest Illinois, the town of Galena makes for a scenic summer getaway. Head to Galena for to stay in a charming B&B, shop its charming boutiques or see colorful balloons take to the skies during events such as the Great Galena Balloon Race.

Get Caught Up in the Romance

Known as one of the most romantic small towns in the country, gorgeous Galena is the perfect place for couples to get away and reconnect. Start with a stroll along winding Main Street, where charming boutiques, art galleries and restaurants are housed in restored red brick buildings that date back to the Civil War. Pick up a beautiful handcrafted pottery piece or a watercolor landscape by a local artist.

Join Galena Trolley Tours to see historic sites that include elegant Victorian mansions and the Grant Home, former residence of President Ulysses S. Grant. Or take one of the spirited daily tours at Blaum Bros. Distilling Co., where you can sample small-batch vodka made with grains grown on area farms. Rent an electric bike from Nuts Outdoors and zoom along scenic country back roads to the award-winning Galena Cellars Vineyard & Winery. Take a vineyard tour and kick back with a glass of wine on the veranda, or take a shot at one of the area’s championship golf courses.

Get a real taste of Galena at one of its downtown restaurants. Log Cabin Steakhouse is known for its Porterhouse, New York Strip and Prime Rib — all huge and bursting with flavor (plus an extensive international wine selection). Fried Green Tomatoes is another favorite, known for its rustic Italian dishes. After dinner, dip into Galena’s nightlife scene. Cheer the colorful Irish dancers at Frank O’Dowd’s Irish Pub & Grill or listen to live music and sample a flight of craft beers at Galena Brewing Company. Cap off your evening with a cocktail (the coconut cream pie dessert martini is yummy) at Miss Kitty’s Grape Escape.

Tuck in for the night at one of Galena’s many cozy bed and breakfasts that dot the picturesque hillsides surrounding the town. Stay at the lavish Goldmoor Inn perched high on a bluff overlooking the Mississippi River or steal away to the uber-romantic Irish Hollow, where you can settle in to your own private English cottage in the woods. Stay in a historic Jail Hill Inn, a 135-year-old, four-story brick building that served as the county jail for nearly 100 years. Or you might want to opt for the all-in-one appeal of the sprawling Eagle Ridge Resort & Spa, home to four championship golf courses, restaurants and the upscale Stonedrift Spa.

Jail Hill Inn is set inside a 135-year-old building atop a hill overlooking the Galena countryside.

Dazzling Events

Great Galena Balloon Race

There's fun for all at this spectacular three-day event! More than 20 hot air balloons, races, a night glow extravaganza, car show, art show, live music and activities for the whole family. The Great Galena Balloon Race benefits JDRF and Camp Hertko Hollow. Since the event began in 2002, it has raised more than $250,000 for kids with diabetes.

Galena Wine Lovers’ Weekend

The largest indoor wine-tasting event in Illinois comes to the Galena Convention Center in March. Area wineries, resorts and restaurants host tastings, dinners and cooking demos as well. Sample the goods from local brewers and distillers, and make it the quintessential Galena getaway by staying in one of the area’s B&Bs and taking a history tour while you are in town.

Art on the Square

Art lovers converge on downtown Belleville for three days over the third weekend in May to attend one of the top-ranked art shows in the nation, Art on the Square. The juried show attracts 100 artists from around the world who work in all mediums. The festival includes an interactive area for kids to create art on the spot, while food vendors serve haute cuisine and fine wine.