Get Outta Town: Snowy, Winter Adventures in Galena

Located less than three hours from Chicago in the northwestern corner of Illinois, on the banks of the Mississippi River, Galena is best known for its beautifully-preserved 19th-century buildings—the downtown Galena Historic District is listed on the National Register of Historic Places—and its stroll-worthy Main Street, which boasts delightful specialty shops, fine and casual restaurants and even a winery.

Don’t think that this delightful town closes up shop for the winter. As soon as snow arrives, you’ll find families snowshoeing, skiing, hiking, cross country skiing and sledding the surrounding hills and forests, while downtown Galena offers a myriad of fun winter events all season long.

Shop the best Main Street in the Midwest

Galena’s bustling Main Street is one of the best in the Midwest. Year-round, it’s packed with a fun selection of clothing, gift and gourmet boutiques, art galleries, antique shops, candy stores and more, but during the holiday season it’s especially delightful thanks to festive decor.

Dreamcatcher (204 S. Main St.) features one-of-a-kind gifts and crafts created by local artists; Poopsies (402 S. Main St.) is the home of all the fun tchotchkes you didn’t know you needed. No visit to Galena would be complete without a stop for a bit of housemade fudge and peanut brittle at Galena Kandy Kitchen (100 N. Main St.).

Hit up charming holiday events galore

During the holiday season, Galena hosts holiday walks, train exhibits, festivals, visits with Santa and Mrs. Claus, tree lightings and more. You might even spy the Grinch in the living windows that line Main Street during the holiday season. There’s are fun, family-friendly events happening regularly, so check the official event calendar before you visit. 

Catch a guided tour of President Grant’s Home

Galena was the home to nine Civil War generals, including Ulysses S. Grant. Upon his triumphant return to Galena in 1865, he was gifted a beautiful brick home. Visit the Grant Home, where the tour guides do a great job of bringing the history down to a child’s level. Your children will get to check out a child’s bedroom from the mid-1800’s — see if they can find the potty! (Hint: Look under the bed!) 

Ski (or snowboard!) the slopes of Chestnut Mountain

Galena’s Chestnut Mountain Resort is located on a picturesque wooded palisade overlooking the mighty Mississippi River. Offering nineteen trails, 220 rolling acres, bunny hills and a 475-foot vertical drop, there’s a slope for both the novice and expert skier.

Even the littlest ones can count on skiing down these slopes as the resort offers private lessons for young skiers ages 4-6 that help them master basic moves and build confidence. Kids ages 7 & up can participate in 2-hour Beginner Hill Basic Lessons.

Trolley Tour

Galena Trolley Tours offers comfy guided tours through the historic area and up and down winding roads from the warmth of a retro trolley.

Skate, sled, snowshoe and ski

At Eagle Ridge Resort, outdoor winter adventures are made easier than ever. Your family can indulge in ice skating, sledding, cross country skiing and snowshoeing, and the onsite Fever River Outfitters has everything you need to enjoy the outdoors this winter, so don’t worry about packing the sleds and skates.

Gear up and head out to their 1.5-acre natural ice pond, perhaps the most idyllic skating backdrop in the Midwest, explore over 7 miles of cross country skiing and snowshoeing trails, sled down the signature 18th hole, or snowshoe on trails that lead through the snowy woods, where you’ll likely spot a soaring eagle. The Nordic Center is open from 9 a.m.-4 p.m. and admission is $5/person, for adults and children. Reservations are recommended and call ahead to check the conditions. After indulging in wintery fun, warm up in the clubhouse or by the center’s crackling bonfire. 

While there are tons of quaint bed and breakfasts in Galena, families love Eagle Ridge Resort for its 63 holes of championship golf, indulgent 6,000-square-foot Stonedrift Spa, indoor swimming pool, award-winning restaurants and outdoor activities galore. The resort is set on a wintery paradise of over 6,800 acres of picture-perfect rolling hills.

Fried Green Tomatoes (213 N. Main St.) is perhaps the most sought-after restaurant in Galena thanks to its locally-sourced, seasonal menu and award-winning wine list. It's cozy, historic setting was once Ulysses S. Grant’s father’s Main St. leather shop. Vinny Vanucchi’s (201 S. Main St.) is another popular option, featuring everybody’s from-scratch Italian favorites.