The 8 Friendliest Little Towns In The Chesapeake Bay

If coastal living means slowing down and enjoying the view, the Chesapeake Bay definitely gets it right. The folks you will meet across this area are arguably some of the friendliest you will find, most of whom are also deeply connected to their communities and neighbors. Year-round farmers' markets, oyster festivals, art walks, and holiday parades are just a few ways the residents of these towns come together, with the following eight towns being some of the best examples.

Urbanna, Virginia

Urbanna has made a name for itself largely thanks to its iconic festivals like the Urbanna Oyster Festival. This festival, taking place on the first Friday and Saturday of November each year, attracts 50,000 attendees from all over and includes activities like an oyster shucking competition, oyster shell painting, wine tasting, and more. December is another great time to visit Urbanna, when many holiday festivities take place. During early December, for example, the annual Tree Lighting, Christmas Parade, and Holiday Home Tour will occur. Travelers needing a spot to stay in town during their visit will find the Chesapeake Inn to be plenty hospitable, a family-owned and operated inn that lies in the heart of town.

Chestertown, Maryland

Chestertown is proud of its American heritage, as seen through the annual Chestertown Tea Party Festival. Each May, this festival commemorates a local legend claiming that Chestertown held its own version of the Tea Party on the Chester River, celebrating the story with a tea toss reenactment, block party, colonial parade, and more. Beyond the tea party festival, visitors can enjoy the Chestertown community year-round at the Chestertown Farmers Market, where local farmers, artisans, and bakers come together in Fountain Park to share their goods with the public. For a live show, check out the calendar at the Garfield Center for the Arts at the Prince Theatre. Cinderella, for example, will be on in December.

Irvington, Virginia

Home to fewer than 500 residents, Irvington is a small and close-knit community that values its local farmers and businesses. The Irvington Farmers Market is the perfect example, held on the first Saturday of each month from May through November and widely regarded as one of the best in Eastern Virginia, featuring over 80 vendors. Many of the town’s seafood restaurants share a strong appreciation for the local seafood industry, as well. Notably, Dredge, a locally owned oyster house, serves freshly sourced seafood. While in town, don’t miss out on the chance to go sailing with Sail & Surf Adventures, a friendly agency that offers both sailing charters and classes.

Cambridge, Maryland

Cambridge was founded in 1684, making it one of the oldest colonial cities in the country. As a result, the town is home to numerous historic buildings and long-standing traditions that remain deeply valued by the community. Travelers looking for a welcoming place to stay during their visit will love the Cambridge House Bed & Breakfast, which is set in a former sea captain’s manor that was built in 1847. Boating fans should schedule their visit for May, during the Cambridge Classic, which is the country’s longest-running powerboat race. For a particularly eccentric event, travelers should consider attending the Ice & Oyster Festival. This January festival is composed of ice sculptures, s’mores, ice skating, live music, and oyster shucking, among other activities.

Cape Charles, Virginia

The Victorian-planned town of Cape Charles is extremely supportive of its art community, reflected in its galleries and annual art events. Each year in May, the Rotary Club hosts the Central Park ArtWalk, which welcomes artists from across the Eastern Shore to display their work at a juried event. There are several art spaces to visit across town as well, such as Lemon Tree Gallery and Studio, which hosts live artist studios, a fine art gallery, a gift shop, and a space for community gatherings. To learn about a bit of Cape Charles’ history, meanwhile, stop by the Cape Charles Museum, which contains both indoor and outdoor exhibits that explore the town’s past.

Chesapeake City, Maryland

Chesapeake City is a historic town along a busy commercial canal, offering plenty of spaces and events for people to gather. Bayheads Brewing Company is a classic spot for residents to get together on the weekend, a local brewery that was established in 2016. Pell Gardens is a lovely place along the water to spend an afternoon, and it also serves as a great viewing area for the Bohemia River Boaters Lighted Boat Parade on December 6, featuring a procession of decorated boats along the canal. For a cozy place to lodge, look no further than the Inn at the Canal, which sits in a 19th-century Victorian-style building.

Easton, Maryland

Easton has an exciting calendar of events that occur throughout the year, making every season a good time to visit! In November, the town hosts the annual Waterfowl Festival, which celebrates and raises money for wildlife conservation through art markets, a waterfowl championship calling competition, food and drink, and more. The Chesapeake Chamber Music Festival is another festival favorite, occurring over two weeks in June at the Avalon Theatre and several other venues in town. Year-round, visitors can enjoy some fantastic art in Easton at the Academy Art Museum, which has more than 1,700 artworks on display.

Onancock, Virginia

Life moves a bit slower and people are a bit friendlier in Onancock, a town of roughly 1,300 people that lies at the mouth of the South Branch Onancock Creek. Here, you can find nostalgic attractions like the Roseland Theatre, a movie theater that was built in 1950 and continues to screen films today. Right on the creek, you can have a wonderful meal at Mallards At The Wharf, where you can enjoy waterfront views while you eat. If you visit Onancock during the second Friday of the month, you can catch the town during its monthly Second Friday Art Stroll, where art galleries, boutiques, and shops stay open a bit later, complemented by live music and wine tastings.

Meet New People Along The Chesapeake

Not only do these towns have some of the region’s best festivals, but they also have plenty of spots to gather with loved ones, whether it be at a local park, a waterfront restaurant, or a brewery. If you are visiting town for the first time, you will likely find a hospitable inn or charter service to welcome you, as well. By the end of your visit, you will likely not want to leave these friendly communities behind!