If you’re looking to hightail it out of Chicago to catch the fall colors, nothing beats a trip to charming Galena, where gorgeous rolling hills and scenic roads surround a quaint, history-filled small town. Though Galena is a wonderful city to visit year-round, it dresses up in its autumnal best and bustles with festive fall fun. Read on to hear just a few of the things you’ll see and do on your getaway from the big city.

galena-bench-sceneryphoto: Galena in the Fall

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.

galena-president-grants-homephoto: President Grant’s Home

Catch a guided tour of President Grant’s Home, a state historic site.
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. The tour guides do a great job of bringing history down to a child’s level, and 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!)

galena-main-street-shopsphoto: Main Street Shops

Shop the best Main Street in the Midwest.
Galena’s bustling Main Street is packed with a fun selection of clothing, gift and gourmet boutiques, art galleries, antique shops, candy stores and more. Atomic Toy (211 S. Main St.) features a wide selection of retro-style toys your kids will love; 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 in for a bit of housemade fudge and peanut brittle at Galena Kandy Kitchen (100 S. Main St.).

galena-black-smithphoto: Galena Blacksmith Shop

See a blacksmith in action.
The Galena Blacksmith Shop (on the corner of Commerce and Franklin streets) is a 100+ year old shop filled with all the tools of the blacksmithing trade. Watch as the blacksmith forges metal at the fire May-October (Fri.-Mon.; 10 am.-4 p.m.)

galena-slidephoto: Alpine Slide

Zoom down an alpine slide.
Why ski when you can slide? If your kid feels the need for speed, the Alpine Slide on Chestnut Mountain (8700 W. Chestnut Mountain Rd.) offers 2,050 ft. of tailored track down to the banks of the Mississippi. Small human-powered cars can take the track fast or slow, depending on your tolerance for speed. All children less than 48” tall and under the age of 7 must ride with an adult. Catch a ski lift back up to the top of the mountain, where on a clear day you can see three states.

galena-desoto-housephoto: DeSoto House

Set off on a trolley tour.
Tri-State Trolley offers comfy, guided tours through the historic area and up and down winding roads.

shenandoah-riding-centerphoto: Shenandoah Riding Center

Enjoy a horseback ride through the countryside.
For a truly unforgettable experience, set off on horseback through meadows and woodlands abundant with wildlife. Shenandoah Riding Center (200 N. Brodrecht Rd.) offers trail rides for both beginner and experienced riders alike. Trail riders must be 8 or older and 65-300 lbs. Little ones can take part in a lead ride, a slow, safe ride with an experienced instructor gently leading the horse at all times.

galena-fall-fair-shoppersphoto: Galena Country Fair

Stroll through Grant Park. Home to the Galena Country Fair (Oct. 8-9), Grant Park (625 Park Ave.) offers walking paths under a canopies of trees and views of historic homes from across the Galena River.

Take a spooky ghost tour. If you’ve got tweens or teens in your group, take a Galena Ghost Tour. Knowledgeable guides will lead you to Galena’s most haunted sites and cemeteries. Prepare to be spooked!

eagle-ridge-resort-2photo: Eagle Ridge Resort


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 6,800 acres of picture-perfect rolling hills and features over 23 miles of hiking and biking trails.

galena-fried-green-tomatoesphoto: Fried Green Tomatoes

Fried Green Tomatoes (213 N. Main St.) is perhaps the most sought-after restaurant in Galena thanks to its locally-sourced, seasonal menu, award-winning wine menu, and cozy, historic setting in what was once Ulysses S. Grant’s father’s Main St. leather shop. Vinny Vanucchi’s (201 S. Main St.) features everybody’s from-scratch Italian favorites — try to snag a table on the lovely terrace. For breakfast, head to the Golden Hen (129 S. Main St.) for down-home-cooking diner-style.

galena-hot-air-balloonphoto: Galena Hot Air Ballon

Don’t Miss
Galena has so many fun, family-focused festivals. Try to plan your visit to coincide with a festival. The Great Galena Balloon Race and Oktoberfest are especially fun for kids and both are great excuses to plan another trip to Galena again next year!

The Thunder Bay Falls (248-268 Thunder Bay Rd.) are splendid, stroller- accessible waterfalls worth a visit.

Have you visited Galena with the family? We’d love to hear about it in the Comments below!

— Amy Bizzarri