Recently voted one of Ohio Magazine’s Best Hometowns, Ashland is proof that small-town charm never goes out of style. Whether you’re looking for a new place to call home or simply a wonderful destination for an autumn family day trip, Ashland welcomes you with open arms.
While there’s plenty to do for solo travelers and couples, this itinerary was created especially for families with younger kids who enjoy creativity, outdoor fun, and a touch of nostalgia.
Stroll Down Main Street to Meet Peggy’s Pumpkin People
Start your adventure in Downtown Ashland, where the sidewalks are transformed each fall with Peggy’s Pumpkin People. This annual tradition fills Main Street with whimsical pumpkin-headed characters. You might spot a construction worker resting on a bench, a musician strumming a guitar, or a pumpkin family enjoying the crisp autumn air. Each figure adds a touch of playful magic to the heart of the city.
Pumpkin People Inspiration
Wondering where these cheerful figures came from? The idea began when Dr. Steve and Peggy Yoder took a family trip to Gatlinburg, Tennessee, and fell in love with the animated pumpkin displays they saw downtown. Wanting to bring that same sense of joy to their hometown, Peggy reached out to the City of Ashland as soon as she returned to see how she could bring some of the mountain magic to Ashland. She even offered to donate the figures herself. With the support of the city, ten pumpkin people made their debut in 2024, and even more joined the fun in 2025. Today, they continue to spread smiles and autumn cheer along Main Street.
Take your time exploring the displays, snapping photos, and visiting a few downtown shops and cafés while you’re there.
Nostalgic Fun at the Ashland-Wooster Drive-In and Relaxing at Brookside Park
This Ashland favorite has been serving up nostalgia and good food for generations. Some of my favorite childhood memories are of sharing a frosty root beer float here with my mom and dad. Now I get to continue the tradition with my grandbabies, which makes it even sweeter.
Just a short drive from downtown, the Ashland-Wooster Drive-In Restaurant is the perfect stop for a classic treat. Order a root beer float and a basket of hand-cut fries, then pull into one of the numbered parking spots where a friendly carhop will take your order. If you’re in a hurry, the drive-thru is always an option. However you order, make sure to try the homemade root beer.
📍 Ashland-Wooster Drive-In Restaurant, 1134 East Main Street (open late February to mid-November)
After lunch, head to Brookside Park, where you can enjoy your meal beside the pond and covered bridge while ducks glide by. The park’s shaded picnic tables and spacious playground, with a Tot Lot for the littles, make it a favorite spot for families. Bring along a book to trade at the Little Free Library near the main playground by the restrooms.
📍 Brookside Park, 209 Parkside Dr.
Creative Time at Tin Can Chandelier and Coffee for the Grownups
When it’s time for a creative break, stop by Goldberry Roasting Company for a locally roasted latte or iced drink. It’s a cozy place to rest for a bit before walking next door to Tin Can Chandelier, a bright art studio and makerspace that invites visitors to explore their creativity.
📍 Goldberry Roasting Company, 1262 Franklin Ave.
There’s no need to register for a class. Choose from a wide selection of walk-in projects, including paint-your-own pottery, canvas painting, and wood sign designs. Spend some time creating your masterpiece, and keep in mind that finished ceramic pieces take about ten days for kiln firing and pickup, so plan accordingly.
📍 Tin Can Chandelier, 1258 Franklin Ave.
A Sweet Ending at Grandpa’s Cheese Barn
Wrap up your Ashland adventure with a visit to one of Ohio’s most beloved roadside destinations, Grandpa’s Cheese Barn and Sweeties Chocolates. This family-run business has been an Ashland landmark for decades and is a must for anyone visiting town.
Browse the shelves filled with local cheeses, sample homemade fudge, or treat yourself to a scoop of ice cream in the indoor café. It’s the perfect place to find a souvenir, a snack for the road, or a little something sweet to end the day.
📍 Grandpa’s Cheese Barn, 668 U.S. 250
Whether you come for the pumpkin people, the playgrounds, or the homemade root beer, Ashland offers the kind of simple, joy-filled experiences that make the best family memories. It’s a hometown that invites you to slow down, savor the moment, and rediscover how much fun a small-town day trip can be.
