Georgetown, Washington, D.C.
to227/Shutterstock Take a stroll down bustling M Street and take in the sights: Packed sidewalks (on the weekends, mostly), stores like Urban Outfitters, Lululemon, and Kate Spade New York, and cobblestone streets. The neighborhood is home to a world-class higher education institution, making it one of the best college towns in the country. Make sure to check out to historical standouts on M Street. The first is Old Stone House, a pre-Revolutionary War home and one of the oldest buildings in the District. Despite being operated by the National Park Service, it’s one of the District’s most haunted locales. The second, made famous by The Exorcist, is the terrifying stone stairs that joggers and movie buffs frequent.
Fort Pierce, Florida
julie deshaies/Shutterstock On the verge of discovery, Fort Pierce has been compared to other notable small towns with charming main streets. Main Street, Fort Pierce has seven National Register of Historic Places locations downtown, which includes the Sunrise Theatre, Moore’s Creek Bridge, and the site Fort Pierce is named for, the original Army post during the Seminole War. There’s also a ghost walking tour through the historic area! Events like the town’s annual celebration, Friday Fest, and its annual reverse raffle auction keep the downtown area lively, along with a farmer’s market—one of the largest in the state—that brings nearly 5,000 people to the main street on Saturdays.
Paso Robles, California
randy andy/Shutterstock Once located near natural hot springs, this wine-country town has a beautiful main square that offers visitors everything from a movie theater and exhibits to restaurants and boutiques. Most importantly, wine tastings are prevalent in the main square, which is dotted with buildings in various styles such as high Victorian and Mexican adobe. Next, check out the nicest small towns in America that everyone should visit before they turn 50.