10 Most Charming Towns in the US

Happy 4th of July! In honor of America’s birthday, I’ve pulled together a list of some of the most charming towns in the United States. The US is incredibly expansive and first-time visitors often hit the big cities and miss out on some of the most charming and friendly places the US has to offer. If you’re planning a trip, I highly recommend putting both big cities and small towns on your itinerary. While big cities are great to explore and check off many bucket list items, some of the best memories are made in the small towns.

Kennebunkport, Maine

Kennebunkport, Maine is a fantastic destination for a classic New England experience. This charming coastal town is full of scenic views, adorable shops, and all the lobster you could ever want. In general, Maine is filled with tiny towns offering an abundance of charm. If you have the time, spend a week driving along the coast. Bar Harbor, Portland, and Camden are just a few suggestions to put on your list. Whether you visit in the summer and can take advantage of the ocean or come for leaf peeping in the fall–you will definitely fall in love with Maine!

Nantucket & Martha’s Vineyard, Massachusetts

When I think of a quintessential summer getaway in the US, Nantucket will always come to mind. This tiny island may be a playground for the rich and famous, but it’s also casual, laid-back, and oh-so-charming. A similar option is Martha’s Vineyard, both islands are easy day trips from Cape Cod. Rent a Vespa and zip around the island, hang out at the beach, and stroll through the downtown for boutique shops and one-of-a-kind restaurants.

Charleston, South Carolina

Hands down, this has to be the most gorgeous city in the US! Here you will enjoy the loveliest walks as the city is lined with beautiful historic homes and lots and lots of southern charm! The city is also packed with great restaurants and excellent shopping and is in close proximity to wonderful beaches.

Naples, Florida

Southwest Florida has some of the best beaches in the US and is often one of the warmest places to visit in the middle of the winter. Naples is known for its darling downtown and high-end shopping and restaurants. Nearby cities like Bonita Springs, Sanibel, Captiva, and Fort Myers offer a more casual Florida vibe and an assortment of activities for a week at the beach.

 Sausalito, California

Sausalito is just under 10 miles from San Francisco and a quick jaunt over the golden gate bridge will land you in the perfect spot for a day trip. This is a unique and artsy town has a houseboat community that lines the harbor. Stroll through town and enjoy one of the many waterfront restaurants.

 Jackson, Wyoming

There are plenty of wild west towns to visit in the US, but this cowboy town will capture the authentic vibe you are looking for and is nearby both Yellowstone National Park and the Grand Tetons to check those off your list! If you visit in the winter you’ll be able to enjoy the Jackson Hole ski resort as well.

Haleiwa, Oahu

No trip to the island of Oahu is complete without a visit to the North Shore and a stop in Haleiwa. Famous for its surfers, laid back locals, and gnarly waves–this small town has been able to preserve the surfer vibe and keep out the commercialism that has overrun Waikiki and other parts of Hawaii. Stroll through the locally owned shops downtown and then make your way to the ocean to check out the world-class surfers.


Healdsburg, Sonoma County, California

Sonoma and Napa Valley are filled with cute towns to visit in California’s most famous wine region. Healdsburg is one town in particular that is not to be missed. From incredible five-star restaurants, to beautiful countryside, this town has everything you need for a perfect visit to California’s wine country.

Laguna beach, California

The southern coast of California is often compared to the French Riviera with it’s 42 miles of beaches and quaint towns that dot the coastline. Laguna beach is a must-see if you’re visiting this part of the world. The secluded coves, spectacular cliffsides and fantastic art community is a traveler’s dream.

Alright, that’s my top 10! I know I missed a ton of other fantastic small towns in the US. What else would you add to the list? I’d love to hear!

Happy Travels!

xo, Jenny

One thought on “10 Most Charming Towns in the US

  1. Esther

    Oh, this post just brought a smile on my face. I mean, these are definately places I have never heard of and that would definately bring colour to a US trip 🙂

    Reply

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