20 Charming Towns for Your Bucket List

Hit the roads less traveled

When planning a road trip, most travelers search out popular destinations. It’s usually cities they’ve read about or towns and attractions that have been recommended by friends or family or on social media. But there are an unlimited number of small towns in America that are worth visiting even if you didn’t know they existed. These 20 unheard-of towns across the U.S. may not be on your bucket list but they absolutely deserve a spot.

St. Simons Island, Georgia

History buffs and beach lovers alike will love this small island town off the Georgia coast. There, you can play a round of golf, fish, visit historical sites, and climb to the top of the St. Simons lighthouse for amazing views.

Bisbee, Arizona © Rex Vogel, all rights reserved

Bisbee, Arizona

Back in the day, Bisbee was a major silver and copper mining hub, but now it’s a quaint small town home to artists and dreamers. With houses on cliffs’ edges and a mine cavern that you can still explore, it’s picturesque.

Jim Beam American Stillhouse, Bardstown, Kentucky © Rex Vogel, all rights reserved

Bardstown, Kentucky

If you like whiskey, Bardstown is a can’t-miss stop. The bourbon capital of the world, Bardstown is to several distilleries including Jim Beam and Maker’s Mark. Be sure to tour My Old Kentucky Home State Park.

Wolfeboro, New Hampshire © Rex Vogel, all rights reserved

Wolfeboro, New Hampshire

This town’s motto is “The Oldest Summer Resort in America” and its prime location on Lake Winnipesaukee proves why. People from all over New Hampshire and Boston vacation here during warm summer months.

Corning, New York © Rex Vogel, all rights reserved

Corning, New York

Wineries and breweries: check. Panoramic views of a gorgeous lake: check. Restaurants filled with top-notch food: check. The Corning Museum of Art is celebrating 50 years and welcoming visitors in a unique way. This southern Finger Lakes community offers something for everyone.

Woods Hole, Massachusetts © Rex Vogel, all rights reserved

Woods Hole, Massachusetts

This tiny, bustling Cape Cod town was once a pass-through destination for Martha’s Vineyard ferry travelers. Now it holds its own thanks to a charming waterfront filled with restaurants and shopping.

Marietta, Ohio © Rex Vogel, all rights reserved

Marietta, Ohio

This town was settled in the 1700s and named in honor of Marie Antoinette. Today, it’s a historic riverboat town that’s ideal for families who seek out vacations full of outdoor adventures.

Cedar Key, Florida © Rex Vogel, all rights reserved

Cedar Key, Florida

This secluded beach community is less about the hustle and bustle and more about small town living. Proof: The restaurant- and buffet-filled streets of the mile-long historic district are filled with bicycles instead of cars.

Fredericksburg, Texas © Rex Vogel, all rights reserved

Fredericksburg, Texas

In the heart of the Texas Hill Country, Fredericksburg maintains a small-town feel while having lots of things to see and do. With its unique German heritage, thriving wineries, and shopping, it’s the perfect getaway. The historic buildings along Main Street are home to over 100 shops. Influenced by the town’s heritage, German and German-inspired food options abound.

Breaux Bridge, Louisiana © Rex Vogel, all rights reserved

Breaux Bridge, Louisiana

Bon Temps et Bon Amis, Breaux Bridge, Louisiana is the place to be.  For toe-tappin’, lip smackin’, ol’ fashioned fun, this little town has something for everyone! Nestled on the banks of the Bayou Teche, Breaux Bridge is a unique community filled with “Joie…

Shipshewana, Indiana © Rex Vogel, all rights reserved

Shipshewana, Indiana

This cute town boasts an Amish community and the largest flea market in the country featuring a whopping 900 booths that cover 100 acres of land. You can munch on treats like sweet corn, while the kids feed animals at the petting zoo.

Fairhope, Alabama © Rex Vogel, all rights reserved

Fairhope, Alabama

Shangri-La may be a fantasy, but you can find a real-life utopia on the eastern shore of Mobile Bay. The city of Fairhope (population, 16,000), founded in 1894 by a society based on cooperative community ownership, was named for its members’ belief that their enterprise had a “fair hope” of success. Ever since, it has beckoned artists and writers. Galleries and studios pepper downtown streets along the waterfront, alongside more than 80 antique shops, small boutiques, and locally owned restaurants. Visit once and you will be back.

Helen, Georgia © Rex Vogel, all rights reserved

Helen Georgia

Helen is a replica Bavarian Alpine town the family will enjoy visiting. A faltering logging town, Helen resurrected itself in 1969 by requiring all of the buildings to be designed in the style of a south German mountain village. It features a downtown with specialty shops offering everything from toys, to pottery, to fudge, and delicious German delicacies like Spätzle and Bratwürst.

Gruene, Texas © Rex Vogel, all rights reserved

Gruene, Texas

Gruene (pronounced like the color green) is designated a historic town by the state of Texas—part of that history is musical. The oldest dance hall in the state (still in its original 1800s-era building) is most famous for its country concerts, but swing, rockabilly, jazz, gospel, and folk musicians take the stage, too. The likes of Willie Nelson, George Strait, Jerry Jeff Walker, and Lyle Lovett have all graced the stage at Gruene Hall.

Ben & Jerry’s © Rex Vogel, all rights reserved

Waterbury, Vermont

Look around town with its brick commercial architecture and sampling of handsome early homes. Most travelers, however, are either passing through or looking for “that ice cream place.” Just to the north of Waterbury along Route 100 Scenic Byway lie a major destination for food-lovers—Ben & Jerry’s, Cold Hollow Cider Mill, Lake Champlain Chocolates, the Cabot Cheese Annex—and Waterbury Center, with its stunning views of the Worcester Range.

La Grange, Texas © Rex Vogel, all rights reserved

La Grange, Texas

You’ll discover a fanciful cache of history and culture in this Central Texas community, a town steeped in German and Czech culture. Much of the town history is encased in dignified old architecture laid in the late 1800s. Many of the original buildings have been renovated and serve as creative outlets. The Texas Quilt Museum is located in two historic 1890s buildings.

Moab, Utah © Rex Vogel, all rights reserved

Moab, Utah

Moab is a small city in eastern Utah famed for its natural beauty and fun escapes for adventure lovers. Moab is a quick drive from two national parks (Arches and Canyonlands) and home to the most popular state park in Utah (Dead Horse State Park). The La Sal Mountain Scenic Loop Road features spectacular scenery ranging from the forested heights of the La Sal Mountains to expansive views of red rock landscape. 

Urbanna Oyster Festival, Virginia © Rex Vogel, all rights reserved

Urbanna, Virginia

A beautiful Colonial port town, Urbanna offers surprises around every corner. Turn off the main road or cruise up the Rappahannock River from the Chesapeake Bay to the charming and friendly historic Colonial port town of Urbanna. Home of Virginia’s Official Oyster Festival, more boats than folks and laid back innkeepers, shopkeepers, and townspeople.

Midway, Kentucky © Rex Vogel, all rights reserved

Midway, Kentucky

Located midway between Frankfort and Lexington, Historic Midway was the first town in Kentucky founded by a railroad (1832). During the railroad’s heyday, the 1930s and 40s, up to 30 trains a day rumbled through the middle of town. The passenger trains dwindled until the old depot was closed in 1963. Now, Historic Midway once again thrives and enjoys its reputation as one of Kentucky’s favorite spots for antiques, crafts, gifts, restaurants, and clothing.

Murphys, California © Rex Vogel, all rights reserved

Murphys, California

The town of Murphys is overflowing with wine courtesy of 25+ tasting rooms dotting Main Street. The microclimates in the Sierra Foothills AVA allow for all kinds of grape varieties but the most common varietals include zinfandel, cabernet sauvignon, and chardonnay. There are also a numerous nearby vineyards that offer on-site wine tasting. 

Worth Pondering…

Once a year go somewhere you have never been before.

—Dalai Lama