Get Ready to Hit the Road! Our Top 10 Small Town Road Trip Destinations for 2022

If you love road trips and think the best part about them are the pit stops, then you’re in luck. We’ve compiled this list of the top 10 small town road trip destinations to help you find your next favorite place to stop on your travels. Whether it’s looking at beautiful landscapes, checking out local landmarks or tasting amazing food, these towns will not disappoint! They offer something for everyone in this Top 10 Small Town Road Trip Destinations in the U.S. list, so grab your friends and family, pack your bags and get ready to hit the road!

10) St. Helena, California

St. Helena, California is a quaint town with a population of just over 5,000 people. It’s famous for its world-class vineyards and wine-making companies like Opus One and Beringer Vineyards that are based out of St. Helena. Locals flock to the many tasting rooms in town, or they head on over to the Old Sugar Mill Distillery where you can sample spirits made from locally grown fruits like apricots and plums.

9) Valparaiso, Indiana

Valparaiso, Indiana is a small town that many have never heard of. Located in Northwest Indiana and about 50 miles from Chicago, Valparaiso has a population of about 30,000 people. But what it lacks in size it makes up for with its charm. Visitors can find French architecture and art galleries throughout the city. One stop that is not to be missed is the Art Center College of Design where visitors can observe students working on their craft.

8) Healdsburg, California

Healdsburg is a small town nestled in Northern California. The downtown area is filled with art galleries, coffee shops, clothing boutiques, and wine tasting rooms – so there’s plenty of things to do if you’re looking for a break from exploring.

7) Waynesville, North Carolina

Waynesville is a small town nestled in Western North Carolina. The town boasts one of the best waterfalls in the state and is also home to two national parks: Great Smoky Mountains National Park and Andrew Johnson National Historic Site. One of Waynesville’s most notable features are its rich Southern traditions, which can be found in everything from its food (which includes delicious chocolate pies) to its arts and crafts.

6) Luray, Virginia

Luray is a small town located in Virginia’s Shenandoah Valley. The town has a population of roughly 3,000 and is situated near Skyline Drive and Shenandoah National Park. Luray offers visitors a variety of outdoor activities including hiking, camping, fishing, boating, and horseback riding.

5) Highlands Ranch, Colorado

Highlands Ranch is a suburb of Denver, Colorado and is home to over 30,000 residents. Highlands Ranch was originally founded in 1981 when it broke off from Douglas County and became its own municipality. The town has been ranked among Forbes’ America‘s Best Places To Live and Money’s Best Places To Live. One of its most popular attractions is its 18-hole golf course designed by Tom Fazio.

4) Newport, Rhode Island

Newport, Rhode Island is a small town that is just the right size. It’s old-fashioned enough to feel like a step back in time but modernized enough that you don’t have to worry about missing out on all of life’s luxuries. From gorgeous mansions in the historic district and coastal views from any vantage point, Newport offers visitors an escape from hectic city life.

3) Winter Park, Colorado

Winter Park, Colorado is one of our top 10 small town destinations in America because it’s perfect for winter sports enthusiasts. Located at 9,000 feet elevation and with an average snowfall of 300 inches per year, Winter Park has some of the best skiing in North America. In addition to great skiing opportunities, Winter Park also offers plenty of other outdoor activities throughout the year such as hiking, mountain biking, dog sledding and horseback riding.

2) Roslyn Harbor, New York

Roslyn Harbor is a charming seaside town on the North Shore of Long Island. With its scenic views, historical architecture, and small-town vibe, Roslyn Harbor is an ideal destination for those seeking peace and relaxation. Visitors can enjoy beaches on both sides of the harbor with one half sandy and calm and the other rocky with strong surf.

1) Kennebunkport Village, Maine

Named America’s Prettiest Seaside Town by Reader’s Digest in 2014, Kennebunkport Village has a long and storied history. Originally called Goose Rocks Beach (named for the abundance of geese that roosted nearby), it was renamed for the Kennebunk River and Portland Street, which connects Boston to Portland, Maine. The town is home to some of America’s most prestigious families, with Bush family members residing there year-round.


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