Sometimes, you need more than therapy. You need a maple latte and a hayride with close friends in small-town America. The golden hour of autumn has finally arrived here, and if you’re not wishing for a Stars Hollow experience, you’re simply not dreaming big enough.
Fall is one of my favorite times to travel, and the cozy towns that dot America’s countryside make it easy to experience in full. You won’t have to travel far to find your own local ghost tour or downtown bookstore. Grab a chunky sweater, turn on Taylor Swift’s evermore album, and prepare to make this autumn a core memory.
There are a few nerdy things you should know about Middleburg, Virginia. It’s the nation’s “horse and hunt” capital, and was an important location during the Civil War. But I’m way more intrigued by the fact that Jackie Kennedy chose Middleburg as her ideal vacation spot. She actually designed and built an estate right outside the city limits. If it’s good enough for Jackie, it’s good enough for me.
In Middleburg, you’ll be just steps away from lush gardens and rolling Virginia countryside. The charming downtown features stone buildings, historic inns and taverns, and a walkable shopping experience that takes you back in time. While you’ll see fall colors from the streets, you can also venture to Shenandoah National Park (45 minutes away) for an impressive display of forest and color.
Some of my favorite places in Middleburg include Cuppa Giddy Up (a coffee shop in an old cellar), the Salamander Resort (if you’re feeling fancy), and Middleburg Books. For the authentic Middleburg experience, visit the Virginia Fall Races. I also love driving the nearby country roads, and discovering historical markers and local markets in Upperville and Aldie.
Poll your Colorado friends and see how many of them actually know about Lake City. It’s considered one of the most rural locations in the lower 48, making it one of the best small-town spots for autumn colors and zero crowds. Sitting just below 9,000 feet in elevation, fall comes early here with bright aspen trees lit up against the Colorado sky. Enjoy breakfast and local music at Euphoria, then go leaf peeping on the scenic Alpine Loop (four-wheel drive required). The Hinsdale County Museum offers ghost tours on Fridays and plenty of spooky stories from miners and prospectors who have made their mark over the years.
Just twenty minutes outside of Asheville, this small town offers a slower pace than you’ll find in the nearby city. You can still visit the famous Biltmore Estate and River Arts District, but you’ll end your day with local pub music and dark sky stargazing. When you’re in Black Mountain, you’ll be steps away from both waterfall hikes and the local pumpkin patch. Hike up to an overlook for autumn colors and then fuel up at Louise’s Kitchen.
The recent filming location of two Hallmark movies, East Aurora is putting itself on the map as one of the coziest small towns for fall. It’s especially known for The Roycroft, a historic arts and philosophy center. The Roycroft’s founder, Elbert Hubbard, was heavily influenced by the ideas of Henry David Thoreau, and this influence is what makes East Aurora so unique today.
The transcendentalist influence means East Aurora is fairly untouched by commercialism and box stores. The town prefers to shop small and support local business owners, usually their friends. As you explore, you’ll overhear conversations between friends and catch gossip about recent business changes. Enjoy autumn colors at Knox Farm State Park, visit Taste for coffee and treats, and explore the famous Vidler’s for souvenirs. No visit to East Aurora is complete without a trip to the historic Roycroft (idyllic with a fall background) or a stop at Millard Fillmore’s home.
Yes, it’s the same Chincoteague featured in Misty of Chincoteague, the popular book by Marguerite Henry. Found off the coast of Virginia, visiting Chincoteague requires a road trip through the Chesapeake Bay region, which is an autumn delight in itself. Once you reach the island, you’ll find yourself in a wildlife refuge that’s home to a charming coastline and wild ponies.
Visit the Assateague Lighthouse, enjoy Sundial Books, and eat some local seafood with a view at the Ropewalk Restaurant. When I visited, I stayed at Miss Molly’s Inn, which brought all the charm of ocean life and historic Virginia together. Of course, no trip to Chincoteague is complete without sighting the wild ponies.
If you want to catch the brilliant colors in Whitefish, Montana, you’ll need to plan an early fall trip. The leaf peeping is best between late September and early October, and since aspen trees are the most prominent, many of them turn color at the same time. Whitefish, Montana, is located just 35 minutes outside of Glacier National Park, so it’s the perfect in-between spot to enjoy the landscape without the crowds. Bike the nearby trails, go on a fishing tour, visit Whitefish Lake, and explore the charming downtown that feels like a Western movie set.
While you’re there, hit the highlights of Glacier National Park during peak leaf-peeping season. Enjoy the Going-to-the-Sun Road, see the colorful Lake McDonald, and hike the iconic Avalanche Trail.
Also known as the Switzerland of America, there’s so much to love about small-town Ouray. Although it’s a popular tourist destination, Ouray still feels quaint and untouched by the modern world. Downtown, you’ll find local chocolate shops, bookstores, and museums all dedicated to keeping the charm alive. Not too far away is Box Canyon Falls, a quick hike that takes you into a deep canyon with rushing water.
When you’re ready to see fall colors, drive the Million Dollar Highway to Silverton. This highway was built in the late 1800s to transport mining supplies across the San Juan Mountains. It’s characterized by steep drop-offs and jaw-dropping landscapes that can’t be fully captured unless you’re there in person. You’ll see sweeping meadows, high alpine forests, and deep mountain ravines. Keep in mind, this mountain highway isn’t for the faint of heart and should be driven with caution. If the roads are snowy, take a four-wheel drive vehicle or don’t go.
I recently completed an Oregon Coast road trip, and Newport, Oregon was one of the highlights. You won’t find it on many tourist guides, which is a shame because this small town has so much ambiance to offer. During the fall months, you’ll experience morning sea mist mixed with the vibrant autumn colors of Oregon’s rainforest. Bundle up in a fisherman’s sweater and check out the Yaquina Head Lighthouse, go tidepool searching at Agate Beach, and visit the award-winning South Beach Fish Market. There’s also the breathtakingThor’s Well, and the coastal highway for rainforest views on one side and ocean views on the other.
This American small town is home to ancient fossil beds, the Oregon Trail, Blue Heart Springs, and Shoshone Falls (called the Niagara Falls of the West). And it deserves a spot on your fall bucket list. You won’t find much of a downtown scene in Hagerman (it’s truly small-town America), but there’s easy access to picturesque fall landscapes in all directions. You’ll find Hagerman just an hour and a half from Boise or three hours from Salt Lake City. If you’re up for a road trip, visit Craters of the Moon National Monument.
Found in West Virginia, Harper’s Ferry is where the Shenandoah and Potomac rivers meet. From overlooks in the park, you can see Virginia, West Virginia, and Maryland all at the same time. Not only does it mark the beginning of the Blue Ridge Mountains, but Harper’s Ferry is a charming town that’s also packed full of Civil War history.
If you’re lucky, you’ll catch a history reenactment. But if not, you can get your own history tour by visiting John Brown’s Fort, the Lockwood House, and St. Peter’s Roman Catholic Church. Walk between stone buildings and admire the autumn colors from the Harper’s Ferry footbridge. If you want to hike, there are plenty of famous trails to choose from, including the Appalachian Trail.
*This article contains affiliate links, so I may receive a commission if you make a purchase. I only partner with brands and businesses that I love and use personally.
Share
Little comforts for your busy life