Road Trip Escapes with Small Town Charm

Road trips are a great way to discover new, close-to-home destinations that you and your family can explore. Here are a few of our favorite charming small towns across the U.S. While they may be off the beaten path, these sleepy villages and historic hamlets are worth including along your road-trip route.

East Coast Road Trippers

Skaneateles, New York—Located in the finger lake region in upstate New York, about 200 miles from New York City, this lakefront village features cute shops and restaurants, as well as boating on Lake Skaneateles and hiking on the nearby Charlie Major Nature Trail. With its first settlers veterans of the Revolutionary War, Skaneateles also offers a bit of American history to explore.

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Shelburne, Vermont—Set on the shores of Lake Champlain, this pastoral town looks straight out of a Norman Rockwell painting. Think clapboard farmhouses, cow-filled pastures, old red barns and orchards filled with apple trees. While summer trips may include cheese making or cow milking, Shelburne Orchards offers apple picking and apple cider in the fall months.

Midwestern Adventure

Bardstown, Kentucky—Forget about wine tasting. Bourbon lovers can sample their favorite brown beverage in this home to several fine bourbon makers. While some remain closed due to COVID-19, several others have taken steps to reopen. For example, paired tastings and one-of-a-kind sampling are currently available at the Bardstown Bourbon Company. Or take a tour and enjoy a tasting at one of Heaven Hill Distillery's three tasting rooms. Besides bourbon tasting tours, Bardstown has a rich Colonial history and a variety of antique shops to explore. 

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Charlevoix, Michigan—This lakefront town in Northern Michigan is the old stomping ground of Ernest Hemingway, who spent time in nearby Horton Bay. Visitors can stop at roadside stands for fresh-picked cherries, visit a local lavender farm or wander the shops and restaurants in downtown Charlevoix.

West Coasting It

Leavenworth, Washington—Not ready to get on a plane to Germany for Oktoberfest? This picturesque Bavarian-style village may be the next best thing. Nestled in the Cascade mountain range, the scenic town features Tudor Revival architecture, beer and wine tasting rooms and even a quirky museum of nutcrackers. Nearby Alpine Lakes Wilderness is the perfect place to social distance with plenty of hiking and biking trails.

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Cottage Grove, Oregon—Seven covered bridges connect this charming country village, located just 20 minutes south of Eugene and near Oregon’s wine country. Here, you can hike trails winding along cascading rivers and past several waterfalls. Or simply pack a picnic and hang out in the local pasture to take in the beauty of this naturally beautiful landscape.

Want to learn more about these charming destinations and other small-town escapes? We can help you plan the perfect road trip!

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