There’s something about fall that makes you want to slow down and take in the crisp autumn air. All of the sudden, there’s nothing we want more than small town charm and cozy days spent wandering local shops, stopping by cafes, and taking the scenic route.
Lucky for us, the Midwest is full of these hidden treasures. So, if you’re craving a weekend of small town charm and peak autumn vibes, these are the places to put on your fall travel list.
Putnam County, IN
45 Minutes from Indy
Fall in Putnam County is the perfect time to slow down and explore all the hidden gems Greencastle has to offer. Spend a leisurely Saturday morning grabbing a coffee and pasty at Breadworks, strolling through charming local shops like Britt’s Blooming Boutique, discovering handmade goods and one-of-a-kind finds from talented local artisans at Creative Castle.
When you’re ready for a break, grab a delicious brunch, a craft cocktail, or a cozy drink at one of the many inviting spots downtown. We recommend checking out the Whisk. With everything conveniently located within an easy walk of the Inn at DePauw, you can spend the day wandering from shop to shop, enjoying local art, great food, and the welcoming small town charm that makes Putnam County such a special fall destination.
Harrodsburg, KY
3.5 Hours from Indy
Spend a fall weekend with friends exploring Harrodsburg, where the peaceful waters of Herrington Lake meet the rolling fairways of Bright Leaf Golf Course. Take in the colorful foliage while fishing, golfing, or hiking. Be sure to visit Shaker Village, a 3,000-acre historic attraction filled with scenic trails, museum exhibits, farm animals, seasonal events, an on-site inn, and restaurant, which makes it easy to stay, eat, and explore all in one place.
Round out your visit with a taste of local charm, from cozy cafés serving Southern comfort food to lively bars like the Vault pouring craft cocktails, local beer, and Kentucky whiskey. With beautiful fall scenery, outdoor adventures, seasonal festivities, and plenty of good food and drink, Harrodsburg makes for an easy and memorable autumn getaway.
Portsmouth, OH
4 Hours from Indy
Escape to Portsmouth, Ohio, for a cozy fall trip filled with charming shops, local restaurants, historic streets, and colorful riverside views. Spend your getaway exploring the picturesque landscapes of Scioto County, from winding hiking trails and Shawnee State Park to family-friendly attractions and seasonal fun at Noble Family Farms.
Make your visit even more festive by timing your trip with Portsmouth’s Oktoberfest, where you can celebrate the season with German-inspired food, beer, live music, and plenty of fall fun. Whether you’re exploring the outdoors during the day or raising a glass with the locals in the evening, Portsmouth offers a relaxed mix of adventure, community, and classic autumn vibes.
Vincennes, IN
2.5 Hours from Indy
Take a trip back in time with a visit to Vincennes, where colorful leaves set the scene for exploring the state’s oldest city. Wander along historic Main Street, browse locally-owned boutiques, grab a slice at Bill Bobe’s, and explore landmarks like Fort Knox II and Grouseland, where preserved architecture and fascinating exhibits bring Vincennes’ role in American history to life.
With its centuries of history, Vincennes is a unique fall getaway for anyone who loves a mix of culture, food, and small town charm.
You don’t have to travel far to find the magic of fall. From discovering local makers to hiking through colorful landscapes, these small towns offer plenty of ways to make the most of the season. So grab your favorite sweater, take the scenic route, and make a weekend of it.
About Sippin’ Sangria
Caroline and Lexa are a traveling duo who have visited several local, U.S., and international destinations together. Through these adventures, they’ve learned the ins and outs of traveling with friends and love connecting with other female travelers. When they’re not booking their next flight, Lexa and Caroline plan trips – honeymoons, girlfriend getaways, weekend trips, etc. Find them at www.sippinsangria.com.
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