Cruising Stories

Cruising Virginia's Eastern Shore


Nestled between the Chesapeake Bay and the Atlantic Ocean, the 70-mile stretch of the southern Eastern Shore is a welcoming mix of quiet towns, unique histories and unspoiled beaches. If you’re looking for weekend getaway or day trip ideas, it’s hard to beat the charm and allure of the coastal towns of Crisfield, Onancock and Cape Charles.


Crisfield aerial | Will Parson-Chesapeake Bay Program on Flickr

Maryland’s maritime history runs deep in Crisfield, and it is deeply connected to Virginia’s waterfront communities. Once known as the “Seafood Capital of the World,” much of the town’s land was created from the massive accumulation of oyster shells. With more than 500 deep-water slips, a protected harbor and ample amenities, Somers Cove Marina is the best place to tie up whether you are staying the day or a few nights.

Like many small coastal towns, Crisfield has struggled to maintain an active retail presence, but they more than make up for this by hosting various annual events that celebrate the boisterous blue crab and seafood industry. Crisfield’s largest event is the annual National Hard Crab Derby, held every Labor Day since 1947. Event highlights include a parade, boat docking and crab picking competitions and The Crab Bowl, which turns Somers Cove Marina into a fairground with rides, concerts, vendor stands and fireworks.

When you visit, be sure to stop by the J. Millard Tawes Museum and discover the rich seafood heritage. Crisfield serves as one of the departure points for visiting Tangier and Smith Islands. You can find ferry transport leaving directly from Somers Cove Marina or in town. Tangier and Smith Islands are fading gems of Chesapeake Bay’s rich history and worth every effort to visit.

Tangier & Smith Islands

Tangier Island lies 12 miles off the western coast of the Eastern Shore. Residents of this small remote island have been working the Chesapeake waters for generations. Their historical ancestry is apparent in the unique dialect spoken on the island. Many of the around 500 residents speak a form of English not heard of anywhere else in the world. This working watermen’s island is home to an unspoiled fishing village with quaint narrow streets and a few places to eat. Unearth their treasured history with a stop at the town’s museum.

Smith Island is a three-by-five-mile island chain and home to around 200 full-time residents. Ewell is the largest of the island chain and where tourist boats deliver visitors. You will find three restaurants and a visitor center in the Ewell community, as well as golf cart rentals to make island exploration easier. Like Tangier Island, the Smith Island way of life is tied to the Bay, and watermen continue to harvest seafood, mostly crabs, clams and oysters.

A Maryland favorite, the Smith Island cake, originated here. Long ago, local ladies perfected a recipe that packs 10 thin layers of cake and icing into a three-inch-tall confectionary treat. You can find Smith Island cakes throughout the Eastern Shore, but savoring a slice while visiting the island is iconic.


Centrally located on the Bay side of the Eastern Shore, Onancock is an inviting small town that was founded in 1680. Its rare deep-water access made it a perfect port, with steamboats traveling between Baltimore and Norfolk and stopping in the waterfront community for supplies and rest.

Today, the town continues to be a place to find rest. Onancock Creek is heavily used by barges and boats, helping to keep the shoaling at bay and creating an easy entry and anchorage for boaters. As you meander up Onancock Creek, time seems to slow down. Drop anchor in one of the available basins for priceless views or make your way to Onancock Wharf & Marina, which is small and can get busy, so reservations are a good idea.

Onancock is easily walkable and bike friendly. Adjacent to the town wharf is the Hopkins & Bro. Store, an historic landmark housing an exhibit and restaurant, Mallards at the Wharf. Stop by for a bit of history and a great meal with a view. As you venture into town, you find quiet streets lined with beautifully maintained Victorian homes and tastefully restored buildings with antique stores, boutiques, art galleries and restaurants.

Beyond the first glimpse of the town, be sure to venture a little farther and visit Ker Place on Market Street and Historic Onancock School. Ker Place is a lovely, restored mansion and curated museum. It’s a great place to learn about Eastern Shore history, and the grounds are vibrant and inviting mid-summer. Halls and classrooms of the Historic Onancock School, which once bustled with students, today serve as work studios and event venues for artists and musicians. It’s free and open to the public.

Cape Charles

Cape Charles sunset | David Broad on Wikimedia Commons

Located at the southern end of Virginia’s Eastern Shore, Cape Charles began as a coastal railroad town. In 1884, a railroad connected Virginia’s Eastern Shore to Norfolk, with ferries for passengers and railcars docking at Cape Charles. In 1885, construction began for a planned community on a gridwork of streets laid out on a parcel of 136 acres. Many of those original structures are still visible in the town, which has grown to become a thriving coastal community.

Three marinas serve Cape Charles: The Oyster Farm Marina at Kings Creek, Town Harbor and the Cape Charles Yacht Center. Oyster Farm Marina is at the North end of town and follows the Cherrystone Inlet into Kings Creek. The entrance can get shallow, so mind your charts or call the marina for local knowledge. The marina has beautifully maintained floating docks, a pool and on-site restaurants, The Oyster Farm and C-Pier.

Closer to the town proper, just off the mouth of the Chesapeake, an 18-foot- deep channel into the harbor provides easy access and docking at the Cape Charles Town Harbor and Cape Charles Yacht Center marinas. The Cape Charles Town Harbor marina offers a mix of floating and fixed docks within walking distance of town. Cape Charles Yacht Center is just across the harbor with well-kept floating docks and a courtesy car or golf cart for guests. While the town is walkable and bike friendly, to get the most out of your visit, renting a golf cart from one of the two local providers is recommended.

Mason Avenue, the town’s main street, will greet you with plenty of coastal shops and several eateries. Grab a dozen oysters and a hand-crafted cocktail at the local distillery, sip hard cider at the cidery or relax on the deck of the Shanty as you enjoy the dockside menu. If you have a sweet tooth, Cape Charles has you covered with three ice cream shops, an old-time candy store and bakeries.

A short half-mile stroll will take you to the Cape Charles Museum & Welcome Center; just head for the water tower painted to look like a lighthouse. A bit farther, but still reachable by foot, bike or golf cart, is the Cape Charles Brewery. They offer a great selection of craft beers and some of the best food around. Make your way to the far end of Mason Avenue to discover Cape Charles’ best kept secret — a mile-long white, sandy beach (that’s very wide when the tide is out) and a fishing pier (no license necessary). The wide beach, shallow water shelf and nearby parking make this beach perfect for those seeking easy access, reduced crowds, calm water and stunning views.

When visiting Cape Charles, take time for a day anchorage just down the bay and explore the ghost ships at Kiptopeke State Park. During WWII, when steel was scarce, 24 experimental concrete ships were commissioned for transport usage. In 1948, nine of these decommissioned vessels were brought to the lower Eastern Shore and intentionally sunk to provide a breakwater for what was then an active ferry terminal.

Today these relics continue to provide a buffer from powerful waves and are now an established wildlife habitat. These behemoth structures rise above the water and flocks of pelicans frolic, fly and feed all around this unique nesting area. The ships are prime fishing spots but maintain a 50-foot distance to avoid hazardous situations. If you have a shallow draft boat, join locals at a day anchorage just south of the ships.

Formerly known as Jackspot, nearby Sunset Beach Bar & Grill has a tiki bar vibe, music, a sandy beach and shaded seating. There is no dock, so boaters roll up into the shallows, drop anchor and wade ashore. The water leading up to the beach is lined with a series of small sandbars that run parallel to the beach, so be mindful of depths and tide changes.

The nooks and crannies of our beloved Chesapeake Bay never cease to amaze me. The excitement of discovering, or rediscovering, hidden gems like these coastal towns is part of what makes the Bay’s Eastern Shore a boater’s delight.

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