The 10 Most Charming Cities in the U.S.

Summer is in full swing! Take advantage of the sunshine and plan a trip to one of the top ten most charming cities in the U.S.

Wondering what makes a city charming?

After compiling a list of 998 mid-sized cities, we researched the walkability of each city, and then ranked them by the number of antique shops, restaurants, and hotels. We also gathered the date each city was founded because history definitely adds to the charm factor.

The following ten cities have a walk score of 80 or higher, meaning you can easily park your car and spend the rest of your day perusing the many antique shops on foot. To ensure an authentic experience, we also suggest taking in some of the local highlights.

Charlottesville, VA

Located in the foothills of the Blue Ridge Mountains, this college town offers fine dining, vineyards, and history, all in a picturesque setting. Whether exploring the outdoors along the Skyline Drive or touring Thomas Jefferson’s old stomping grounds, every visitor is sure to be charmed by this city.

What to do:

Hudson, NY

Known amongst art lovers for the Hudson River School, this area saw highs and lows through multiple industrial booms but luckily for traveller, it is yet again on the rise. Just a two hour train ride from New York City, creative and culinary influences are blending with the rich, historical culture.

What to do:

Montrose, CO

Downtown Montrose is filled with galleries, eclectic shops, restaurants, and more. The Public Art Experience brings sculptures on loan to display around town. Keep your eye out as you walk down Main Street. Locals love to take in the nature that surrounds this creative community from Black Canyon National Park to the east and the Uncompahgre Plateau to the west.

What to do: 

  • Peruse the galleries on Main Street
  • Rafting or kayaking in the Gunnison Gorge
  • Family owned Trattoria Di Sofia Italian restaurant

Astoria, OR

Situated near the mouth of the Columbia River on the Pacific, Astoria is a port city distinguished for being the first permanent U.S. settlement on the west coast. Astoria has a gritty exterior but an artistic heart with fisherman poets, loggers who double as baristas, and several galleries to peruse.

What to do: 

Sonora, CA

Sonora lies in the heart of California’s Gold Country near the Sierra Nevada Foothills. This town is a history buff’s delight with historic homes, antique shops, and old fashioned gardens lining Main Street. Outdoorsmen will also enjoy all of the recreational activities available, including hiking, swimming, and golfing.

What to do: 

  • Walk down Main Street
  • Hike the Dragoon Gulch Trail
  • Shop the antique stores

Walla Walla, WA

For small town friendliness combined with incredible eateries and fine wines, visit Walla Walla. The Walla Walla Valley is known as one of the most fertile areas in the country. Be sure to explore the wineries and tasting rooms as well as the funky shops that line Main Street.

What to do: 

  • Visit the seasonal markets
  • Attend an outdoor concert
  • Stroll Main Street

Athens, OH

Home to Ohio University, Athens is a quirky little town located in southern Ohio. Stroll down Court Street, eat at the old school diner, and take in the Ohio University campus. Branch off of the main drag a block to enjoy the fine dining at Zoe.  

What to do: 

Jackson, WY

Jackson is one of the fastest growing small towns in America and it’s easy to see why. Within reach of both Grand Teton National Park and Yellowstone National Park, the town is surrounded by beautiful mountain scenery. The town square has developed into a large shopping and eating district, so start your exploration there.

What to do: 

  • Ride the aerial tram
  • Explore outdoor activities from hiking, biking and rock-climbing to fly-fishing
  • Visit the antique shops

Helena, MT

Founded during the Montana Gold Rush, Helena is the capital city of Montana. Early wealth led to elaborate Victorian architecture to keep and eye out for when perusing this capital city. Hiking, biking, fishing, and thrift shopping are some of the local’s favorite activities.

What to do: 

  • Take a dip in the Broadwater Hot Springs
  • Grab cajun at Cafe Zydeco

Bennington, VT

Bennington is a small town lauded for its textiles, pottery, and ironwork. Visit the historic sites and covered bridges to really take in the small town charm. The mountainous landscape and Revolutionary War history are sure to delight.

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