Food and Wine Weekend Getaway in Galena

  • Distance from Chicago: 164 miles
  • Best time: June to October; December
  • Best for: Girl's GetawayRomanticFood and Wine

Saved from the glaciers that flattened most of the Midwest, Galena boasts hills big enough for decent downhill skiing and an autumn beauty that draws fans far and wide. Bursting with charm, this small town of just 3,400 people grew in the 1820s and '30s as a lead-mining hub before an economic downturn limited new construction. It wasn't until nearly a century later that historians and artists recognized its topographical and architectural significance. Now, more than 85 percent of its nineteenth-century buildings are listed on the National Register of Historic Places, and visitors adore its small-town hospitality and romantic character. – By Elisa Drake


Galena Cheat Sheet

View a printable list of all sights, restaurants, entertainment, and hotels from this itinerary. View

1Transition from workweek craziness with a soothing treatment at Stonedrift Spa at Eagle Ridge Resort and Spa. You could go for the Mystic Sage Stone Therapy that incorporates organic herbs and warm stones to help you de-stress or choose the ancient Bamboo Thai massage. If you're not already staying at one of the inn's rooms or renting one of its luxury residences, you'll pay an extra $20 day fee for the spa, but you won't mind a bit after settling into the relaxing steam room.

2Now that you're fully weekend-ready, head over to Galena's favorite Italian spot, Fried Green Tomatoes. Situated in the storied nineteenth-century Dowling building, its exposed brick and stone walls and linen tablecloths create a homey, but upscale, feel. Be sure to start with the eponymous veggies, then try the lobster ravioli, espresso-encrusted filet, or pork osso buco.

3Wind down for the night gazing over the Mississippi River with a glass of vino from the Stone Cliff Winery in nearby Dubuque, Iowa, where owners Nan and Bob Smith offer free live entertainment.


1Surround yourself with locals and a rotating gallery of local art at the low-key Otto's Place Café and Lounge. The airy, sunny space with its wood floors and mission-style furnishings is surprisingly conversation-conducive, and the menu is surprisingly inexpensive. For a sweet start to your day, go for the house-made coffee cake. For something more hearty, try the biscuits and gravy or spinach, mushroom, and sundried tomato omelet.

2Now, just sit back and take in the sights and informational commentary on a Galena Trolley Tour. You could take the two-and-a-half-hour tour or pack in an overview of this historic area on the one-hour tour.

3Your trolley tour only showed the Belvedere Mansion exterior, so head back and take the half-hour walk through this ornate 1857 Italianate twenty-two-room home built for steamboat magnate and ambassador to Belgium, J. Russell Jones. The vast and varied collection of Victorian antiques includes the famous green drapes from Gone With the Wind.

4Back on Main Street, the Galena Brewing Company pours its own local brews, like a dark stout and the award-winning nut brown ale. Taste one for a midday break, along with the tapas menu featuring suggested beer pairings, such as an amber ale with the apple bacon cheddar crostini. There are also soups, salads, and sandwiches, served with homemade beer bread.

5Brush up on Civil War-era history at the Ulysses S. Grant Home, both a National Historic Landmark and on the National Register of Historic Places. The former home of the eighteenth president was built in 1860 in an Italianate bracketed style and is replete with furnishings his family once used.

6Set off on a balloon ride with Galena on the Fly for a memorable sunset. Be sure to pack your cameras because the vista from aboard this one-hour flight will make you forget any fear of heights you had. Afterward, celebrate with a champagne toast—a tradition dating to the very first hot-air balloon rides in France.

7When you've come back down to earth, head over to Perry Street Brasserie, an intimate French-inspired forty-seat restaurant. Husband-and-wife team Steve and Renee Dowe treat their staff like family, and it shows in the meticulous service. But it's the food that gets top billing, from the tempting bread to the signature chocolate cup for dessert. In between, monthly-changing entrees include spot-on beef tenderloin and yellowfin ahi tun with Thai garlic chili sauce.


1A leisurely breakfast is in order, and the Courtyard Restaurant at the DeSoto House Hotel fits the bill. Choose from among the carving station, made-to-order omelets and waffles, biscuits and sausage, pastries and fruit, French toast, and more at the buffet in the four-story atrium of this hotel that once served as Ulysses S. Grant's campaign headquarters.

2Hark back to bygone days at the Old Blacksmith Shop. Check out the original tools used by Willard Richardson, who crafted his wares here from 1929 to 1979 and watch the modern-day blacksmiths who often work in the space.

3While we don't condone drinking and driving, you'll be perfectly fine with a few tastes and some bottles to go from the family-owned Galena Cellars Vineyard and Winery. There are more than twenty-five varietals available, plus locally produced cheese and sausage.

Where to Stay

Overlooking the Mississippi River, the idyllic Goldmoor Inn (rooms from $315/night; 2-night minimum on weekends) bed and breakfast has all the trimmings of romance: cozy nooks for cuddling, a fireplace surrounded by comfy couches and chairs, and well-appointed guestrooms with raised hot tubs.

When you're looking for simpler accommodations, check into Chestnut Mountain Resort (rooms from $89/night). In the winter, this 120-room hotel about eight miles southeast of downtown Galena draws crowds for its downhill ski runs, but in summer there are five miles of hiking trails, an alpine slide, and mini and disc golf courses.

When to Go

Any season makes sense for a trip to Galena. In winter, the town's charm takes on a holiday spirit with twinkling lights, horse-drawn carriage rides, and Main Street windows decked out for the season. Roaring fireplaces create intimate scenes, while the downhill runs of Chestnut Mountain Resort heat things up too.

Spring and summer bring out the beautiful greens of the rolling hills and the rainbow of colors that dot the many carefully tended gardens. It's often the busiest time of the year for visitors, and therefore, typically the most expensive, because Galena makes the perfect place for a casual stroll arm-in-arm down Main Street. Come fall, it's the lingering warm days, with off-peak prices and the vibrant hues of changing leaves that bring out the throngs.

How to Get There

By Car: With limited public transportation from Chicago, it's best simply to drive. The three-hour trip is an easy one on I-90 West. Be sure to have your I-Pass or some money ready for tolls. Take the exit toward 39 South/Route 20 to Rockford (not the Business Route 20). Continue on 20 West to take you right into Galena.

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