Fall Getaway to Galena, Illinois | Midwest Living

Fall Getaway to Galena, Illinois

When leaves turn to gold in a town built on lead, Galena alchemy is formed. See our guide of things to do (and of course eat) in Galena this fall.

Galena, Illinois

Photo Courtesy of Visitgalena.org.

Galena was named after a precious lead mineral abundant beneath the town's surface. Four decades since the last mine shut down, a movie set-perfect Main Street makes this northwest Illinois town a golden getaway. After mining the shops, escape to the country for hiking, biking and the leafy riches of fall.

Church in Galena


Hit the Streets 

Main Street spans 140 mostly 19th-century buildings housing 100-plus shops, restaurants and independent inns.

Main Street in Galena, Illinois

Main Street in Galena. Photo Courtesy of Visitgalena.org.

To experience max charm, go to jail. Galena native Matthew Carroll re-opened the old county slammer as Jail Hill Inn in 2016. This year, TripAdvisor named it the best inn or bed-and-breakfast in the country. Find former prisoner names carved into the windowsill in suite 301.

Jail Hill Inn

Jail Hill Inn. Photo Courtesy of Jail Hill Inn.

A splurge stay includes a generous happy hour and a three-course breakfast that may be the tastiest meal in town. Somehow it remains mostly a one-man show, with Matthew handling daily reservations, check-ins and the bulk of the kitchen work.

For another historic stay, check out DeSoto House Hotel. Abraham Lincoln once gave a speech from the balcony, and it served as presidential campaign headquarters for local hero Ulysses S. Grant. At the Ulysses S. Grant Home nearby, guided tours run Wednesday through Sunday. Ninety percent of the furnishings are original.

You can easily spend a day following Main Street eye candy into shops. Sample nearly 100 flavored oils and vinegars at Galena Garlic Company. Peruse fun cooking gadgets and books at The Grateful Gourmet Company. Or stockpile absurdly hot sauces from the arsenal at Galena Canning Company.

Along the way, pop into one of Galena’s dining mainstays: Fritz and Frites combines German and French flavors in a cafe setting. Book a dinner date at Fried Green Tomatoes for wild mushroom ravioli and other Italian fare. Durty Gurt’s is as quirky and casual as it sounds, serving up loaded burgers, rum buckets and boozy shakes. If fright-seeing is more your style, Amelia’s Galena Ghost Tours and several other businesses lead haunted walks and rides into pubs, outside cemeteries and to other public spaces after dark.

Fried Green Tomatoes. Photo Courtesy of Visitgalena.org.

Galena, IL

Galena is lllinois’ second-most visited city for tourism. What does that mean for a town of 3,500? There are more ghost tour companies than grocery stores, and guest beds reportedly outnumber locals. Photo Courtesy of Visitgalena.org.

Raise a Glass

Savor a cocktail at Blaum Bros. Distilling Company. Or you can line up a flight—bourbon, rye, gin and HellFyre (vodka infused with peppercorns, habanero and jalapeño). Throw them back in a mod tasting room of exposed beams, wooden barrels and plush leather couches. Brothers Mike and Matt Blaum opened this delicious spot on the edge of town in 2013.

Blaum Bros. Distilling Company

Blaum Bros. Distilling Company. Photo Courtesy of Illinois Office of Tourism.

About 6 miles from downtown, don’t expect farm animals or grain in the large barns at Galena Cellars Vineyard and Winery. They’ve been repurposed for winemaking and storage (50 varieties). After touring the grounds, sample the goods at a tasting in the old country farmhouse—with live music Saturdays through September.

Galena Cellars Vineyard and Winery

Galena Cellars Vineyard and Winery. Photo by Bob Stefko.

Chicago-born Rosario Bruno taps his Italian roots for his wines at Fergedaboudit Vineyard and Winery. Staples include Cabernet Franc, Marechal Foch and Leon Millot (which uses an Illinois grape for a Chianti-style wine).

Get Out of Town 

Galena sits on the southern edge of the driftless region, where the rivers and rocky bluffs dodged the flattening force of glaciers long ago. Check out the fall colors by foot or on a pedal-assist bicycle.

Mississippi Palisades

Lookout Point View at Mississippi Palisades. Photo by Bob Stefko.

Perched above Lake Galena, Eagle Ridge Resort and Spa is a central hub for The Galena Territory, a scenic development of vacation homes. Guests can access Thunder Bay Falls spilling out of the lake. Arrive early to beat wedding photographers to the popular rocky, misty backdrop.

Galena on the Fly Hot-Air Balloon Tours

Departing from Eagle Ridge Resort and Spa, Galena on the Fly hot-air balloon tours soar up to 3,000 feet above the rolling landscape of water, fields and trees. Photo Courtesy of Illinois Office of Tourism.

For thigh-burning hikes, plan a 30-minute drive southwest to Mississippi Palisades State Park. You can string together more than 5 miles of short trails. Expect some steady uphill climbs, such as Sentinel Trail, to reach rock faces where you might spot eagles. In nearby Savanna, grab a bite at Poopy’s, a roadside restaurant with three bars that draws the biker crowd. Or check out Frank Fritz Finds, an antique store run by the American Pickers co-host.

Sentinel Trail at Mississippi Palisades

Sentinel Trail at Mississippi Palisades. Photo by Bob Stefko.

In 1900, an archaeologist documented 51 Native American mounds at what’s now Casper Bluff Land and Water Reserve, 5 miles outside Galena. Today you can look for some of them while hiking the 85-acre preserve, which is popular with bird-watchers and offers grand Mississippi River vistas.

Cyclists can cover 8 miles on the Galena River Trail. Rent a battery-powered e-bike from Fever River Outfitters to make it a sweat-free affair. Some rental packages include access to Chestnut Mountain Resort (alpine slide included) or Galena Cellars, with a shuttle ride back to avoid any buzzed biking.

E-Bike Ride Through The Countryside

E-Bike Ride Through The Countryside. Photo Courtesy of Visitgalena.org.

Fall Dates

Rather than throw clay on a wheel, potter Paul Eshelman carves plaster models with woodworking tools to craft ramen bowls, mugs and other ceramic vessels. Step into his workspace (in Elizabeth) and several others in the area during the self-guided Twenty Dirty Hands Pottery Tour. The event, October 18–20, 2019, draws visitors into towns and scenic nooks beyond Galena.

Potter Paul Eshelman

The waft of funnel cakes and hand-cut fries leads to Batik bags, small metal sculptures and rare folk art creations. Pictured is Potter Paul Eshelman. Photo Courtesy of Eshelman Pottery.

At the Galena Country Fair, the waft of funnel cakes and hand-cut fries leads to Batik bags, small metal sculptures and rare folk art creations in Grant Park. More than 150 vendors of fine art and food will gather Columbus Day weekend, October 12–13, 2019, for the 40th annual celebration.

Flames blast into the sky to illuminate costumed performers and elaborate street floats at the annual Halloween Parade and Festival. After 40 years, the Main Street event has become one of the city’s biggest, so book your lodging far in advance of the October 26, 2019, festivities.


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