10 Prettiest Small Towns On The Chesapeake Bay
As the largest estuary in the country, Chesapeake Bay has plenty of nooks and crannies to explore. With so many options, narrowing down the towns can be the hardest part of vacation planning! The following 10 towns are arguably some of the prettiest, offering attractions like maritime forests, oyster festivals, 18th-century inns, and sailing charters. You will certainly be in a seaside spirit by the end of your trip!
Cape Charles, Virginia
In addition to its gorgeous beaches, Cape Charles is surrounded by maritime forests and sand dunes. Travelers wanting to explore this nature can start out at the Cape Charles Natural Area Preserve, which is home to forested uplands, an elevated boardwalk, and numerous protected migratory bird species. Afterwards, head over to the Savage Neck Dunes Natural Area Preserve, a 298-acre preserve with dunes, beaches, and one of the largest populations of northeastern beach tiger beetles in the world. To relax after a day out in nature, visitors can spend the night at Bay Haven Inn, which is housed in a historic 1906 colonial revival-style home.
St. Michaels, Maryland
If sailing and maritime history sound like your idea of a relaxing vacation, you will love St. Michaels. Visitors can explore the bay’s waters by signing up for a sailing excursion with Sail Selina II. This beloved sailing charter offers day sails, champagne sunset sails, moonlight cruises, and other scenic excursions. To learn more about the Chesapeake Bay’s history, spend an afternoon at the Chesapeake Bay Maritime Museum, which features exhibits on the region’s environment, history, and culture. The best way to conclude the day is at one of St. Michael’s seafood restaurants! Chesapeake Landing is a great option, serving fresh and locally caught seafood in town for over 30 years.
Urbanna, Virginia
The charming town of Urbanna is perhaps most famous for the annual Urbanna Oyster Festival that it hosts each year. This festival, which was designated as the “Official Oyster Festival of the Commonwealth” in 1988, features more than 50 food vendors and every type of oyster imaginable. In the summer, travelers can also grab fresh food at Urbanna's Farmers Market, which takes place on the second Saturday of each month. For a trip back through Urbanna’s colonial past, stop by the Urbanna James Mills Scottish Factor Store Museum & Visitor Center, which is situated inside a historic, 18th-century building.
Oxford, Maryland
Oxford is home to the oldest privately operated ferry service in the United States, running continuously since 1683. Visitors can book a ride on the historic Oxford-Bellevue Ferry, which travels between Oxford and Bellevue. After the ferry ride, continue enjoying the sunshine at Oxford Conservation Park, which has a short nature trail that winds through a rehabilitated wetland environment. If you are planning to spend the night in town, there are plenty of historic inns to choose from. The Robert Morris Inn, for example, is located along the waterfront and dates back to 1710.
Chesapeake City, Maryland
Much of Chesapeake City’s original 19th-century architecture continues to stand today, transporting visitors back in time. Visitors can immerse themselves in this history by spending the night at the Inn at the Canal, a Victorian-era 19th-century inn. To learn more about the town’s history, make sure to visit the Chesapeake City Museum, which is set in a brick building from 1870 and has an extensive collection of artifacts and archives. If you want to enjoy the afternoon on the water, reserve a cruise with Chesapeake City Water Tours, which offers sunset cruises, sightseeing canal cruises, mimosa brunch cruises, and more.
Rock Hall, Maryland
Nicknamed the “Pearl of the Chesapeake,” Rock Hall is filled with sailing charters, boat rentals, and seafood restaurants, promising you the ultimate Chesapeake Bay experience. Travelers craving a day on the water can arrange an excursion with Chesapeake Bay Sailing Cruises, a local company that has been providing sailing services for 25 years. If you prefer to explore the waters at your own pace, East Neck Boat Rental offers boating rentals, along with crabbing and fishing supplies for travelers eager to catch their own seafood. For a good meal after your adventure on the water, Harbor Shack, a waterfront bar and grill, serves shrimp, crab cakes, burgers, and fish, among many other dishes.
Easton, Maryland
Easton has a lively arts scene, making it easy to fill the weekend with theater performances, art galleries, and museums. The Avalon Foundation hosts monthly live performances, including jazz shows, guitarists, and rock bands. The Academy Art Museum is another artistic pillar in town, showcasing exhibitions from the 17th century through today, along with offering art classes for both children and adults. If you are looking to purchase a piece of art or simply want to browse, Troika Gallery is a great stop, showcasing work by numerous artists and rotating exhibits throughout the year.
Cambridge, Maryland
With a history dating back to 1684, Cambridge is one of the country’s oldest colonial towns. The Richardson Maritime Museum is the perfect place to learn more about this history, exhibiting the town’s heritage on a beautiful, four-acre waterfront campus. Each Saturday morning, visitors can sign up for an exciting sailing excursion with Skipjack Nathan of Dorchester, who offers two-hour-long sailing charters through the town’s waters. Travelers who will be in town in October should attend the Taste of Cambridge festival, a food-centered event with a cook-off, vendor market, live music, and a kids' zone.
Irvington, Virginia
Home to fewer than 500 residents, you won’t find many places more laid-back than Irvington. Travelers hoping to get out on the water can rent a kayak or book a fishing trip with Tackle Cove, a local outfitter in the area. For lunch, there are plenty of cute cafes and restaurants to check out, such as The Office Bistro, which serves specialty dishes like baby back ribs, pizzas, and cobb salad. The Tides Inn is a great place to end the day, offering water-view and resort-view rooms with suites, king beds, and double bed layouts.
Onancock, Virginia
If you enjoy a little bit of everything on vacation, you will love the variety of attractions in Onancock. Theater fans can catch a show at the North Street Playhouse, the only regularly performing theater on Virginia’s Eastern Shore. Starting in July, the theater will present Long Beach Blanket Bingo, a musical by James Berg and Stan Zimmerman. From April through October, travelers can explore the scenic South Branch of Onancock Creek by renting a kayak or stand-up paddleboard from Burnham Guides Paddle & Bike, a local paddling outfitter. For a souvenir, browse one of the local shops or boutiques, like North Street Market, which specializes in fine wines, cheeses, and gourmet foods.
Summer is in full swing, and you deserve a vacation. If you need help deciding where to start this year, make sure to keep these 10 towns in mind. Small towns like St. Michaels will give you a trip filled with maritime history, while other destinations, like Cape Charles, guarantee an exciting trip in the great outdoors. All you have left to do is make the hotel reservation and hit the road!
