7 Breathtaking Towns To Visit In Chesapeake Bay
Chesapeake Bay, the largest estuary in the US, stands on its own as a world-sought-after destination for its deep history, fantastic seafood, and breathtaking beauty. The tiny towns dotting the eastern shore in Maryland and Virginia offer a taste of the unique maritime way of life and southern culture at the hospitable local hands.
Williamsburg abounds with shopping and dining through its Colonial Williamsburg, as well as recreational opportunities like Water Country US. Saxis Island, home to one of the largest seafood landing ports on the Bayside of Virginia's Eastern Shore, features unrestricted bayfront views to mingle by the docks among local watermen, crab shanties, and heaps of oysters before a stroll through the local market and a tiki-themed dinner.
Crisfield, Maryland
When you visit this breathtaking, historic town on the eastern shore, note that what you see and experience has been lovingly shaped by the rough-handed local "Watermen." From the thriving family businesses generations in fishing the bay's teeming waters to the local seafood restaurants and fish markets, the small-town shops lovingly promote the local fruits of labor through craft, thought-out souvenirs, and such. Wake up early enough to meet the sunrise and a dozen hard-working crabbers, out before daybreak, responsible for the city's Crab Capital of the World moniker, and working on your dinnertime, the Soft-Shelled Crab, a local delicacy.
The local accent, unique to Crisfield and the neighboring Smith Island, is "old English," with speech patterns reminiscent of the original British settlers. Another idiom from colonial heritage is that, most likely, one will sport the name William and another one will be a “Smith." Part of the "Delmarva" region, colloquially Delaware, Maryland, and Virginia, the "Gateway to the Chesapeake Bay," Crisfield is in a tight cultural embrace with the bay. So from now and until the spectacular sunset from the City Dock, there's so much to do here, from unique festivals to fishing, boating, and seaside strolls. Don't miss the Cove Marina with a giant rubber ducky and 515 slips, as well as the cozy Wellington Beach.
Havre de Grace, Maryland
Much like its name and the scenic location on the largest estuary in the US, Havre de Grace is a breathtaking main street community. Nestled where the Susquehanna River meets Chesapeake Bay, Concord Point Park is popular for waterside recreation and the best vantage point to catch the sunset, overlooking the iconic Concord Point Lighthouse. Big on culture, including the Decoy Museum, the regional arts scene encompasses several public art installations at the park's scenic spots, as well as neighborhood "art"ractions, and, most recently, two great public events, with one on the nose.
Opening on May 24, visitors can enjoy free viewing of work created by plein air artists during the annual Secret Garden Tour event against the local beauty through Havre de Grace Gardens until July 25. Part of the Harmers Town Art Centre, the interactive Graw Alley Art Park Graw Alley is a unique, one-acre private alley named after the city's horse racing track from a century ago. From waterfront shopping to fantastic seafood and remarkable history, there are so many ways to explore Havre de Grace along the Havre de Grace Promenade and Boardwalk, as well as the Havre de Grace Maritime Museum.
Onancock, Virginia
Onancock, the heart of the Eastern Shore, rests scenically between the bay and sea, so you're in for breathtaking water views. Looking back from when the area dazzled the seafaring Captain John Smith over four centuries ago to the present-day population of around 1,200, Onancock weaves a tapestry of old and new, with museums, cuisine, and art galleries peppering the vibrant downtown. Preserving its traditions and small-town character, visitors can enjoy southern hospitality with a maritime taste at pubs, five-star restaurants, premium bed and breakfasts, and boutique hotels.
As a coveted art hub, its converted historic high school flaunts individual artisan studios, while the live theatre presents Main Stage productions in a collaboration of professional and local actors, including apprentices from high school. The Roseland Theatre, a 1950s cinema, is popular for its old-time charm and new releases, as well as the International Film Festival, a deeply discounted renowned foreign film once a month. The ferry to Tangier Island offers access to the bay's hidden treasures from May through October, just in time for the local farmers and artisans' outdoor market in town with live music. Don't miss the local Maritime Museum, the Eastern Shore Historical Society, and the best sunset from the shore of Onancock Creek after a day of paddling.
Rock Hall, Maryland
This waterman’s town rocks Chesapeake Bay's edge at the Chester River meeting point and bay. Rock Hall, a favorite traveler's stop, rocks expansive water views and a family-friendly feel that attracts outdoor enthusiasts. With an amazing seafood scene and shopping opportunities, visitors can enjoy unique heritage through museums. The Rock Hall Museum is a decoy-carving shop replica with marine trade artifacts and vessel models, as well as fishing and oystering exhibits, while the local Waterman's Museum at Haven Harbor Marina rocks much of the same plus a replica waterman's shanty house and old photographs. While its Chesapeake neighbors are avid fishermen, Rock Hall loves sailing.
The unique Rock Hall Landing Marina can be your base, with an onsite motel, pool, WiFi, bathhouses, a fire pit and BBQ, bikes, and more. Visitors can take a sail on a crewed charter or learn the art from the Delmarva Sailing School. Shardana Sailing Charters offers up-to-full-day sails, sunset outings, and even multi-day trips with a storyteller. Home to seven different nature trails and the Tundra Swan Boardwalk for strolls and fishing, the Eastern Neck National Wildlife Refuge is a paradise for wildlife lovers. Its Visitor Contact Station is a historic hunting lodge with exhibits on man's connection to habitat through history and a gift shop. Visitors can connect with wildlife today or relax with stunning views at the Ingleside Recreation Area and Bogles Wharf.
Saxis, Virginia
The unique town of Saxis, or Saxis Island, on Virginia's Eastern Shore is one of Chesapeake's last hidden gems. Without condos crowding the bayfront, the views are open and expansive, while the hotels are homey and not expensive. Visitors can mingle along the docks with local watermen, crab shanties, and heaps of oysters on the way to a local market and your ultimate dinner plate at a restaurant over a glass of wine, like Capt E's Hurricane Grill & Tiki Bar. Located at the southernmost point of the island, near Saxis fishing pier, this is where most activity occurs, by one of the largest seafood landing ports on the Bayside of Virginia's Eastern Shore.
Incorporated in 1896 and home to only 350 people today, visitors can experience the industry-based tradition firsthand and learn about Saxis' role on the regional scale in agricultural and seafood production efforts, from harvest to wholesale. Flaunting a fleet of 57 workboats and 13 seafood businesses next to Starling Creek, cultural attractions like the Seafood Saxis Island Museum & Old Crockett Store enrich every relaxed coastal getaway. Otherwise oblivious to the daily rut and rush, the friendly locals enjoy sharing their fulfilling lifestyle of the olden days' charm in a remote feel with a salty taste of history on a stroll through the Pink Pirate, a seafood market.
Williamsburg, Virginia
Williamsburg, the "Colonial Capital" of Virginia, is known worldwide for its restoration efforts. Flaunting an 18th-century American architectural landscape called Colonial Williamsburg, it really is an exceptional historical, cultural, and even recreational area. Featuring regular events and something engaging for every age throughout the year, visitors can enjoy the specific ambiance on top of the traditional southern hospitality, which is a standard operating procedure in the Historic Triangle. The DeWitt Wallace Decorative Arts Museum and the Abby Aldrich Rockefeller Fork Art Museum at Colonial Williamsburg connect visitors to fine works of art from around the world.
Home to endless dining establishments of any style, budget, and cuisine, shopping opportunities abound in the area without stepping onto the preserved sites. From Merchants Square, New Town, and the Farmer's Market, it's easy to find both bargains and luxury items through the outlet malls. Don't miss the Muscarelle Museum of Art at the College of William and Mary, while the outdoorsy enjoy golf courses at Kingsmill or watersports on the James and York Rivers or the Chesapeake Bay. Couples can take sensual strolls through the lush Busch Gardens theme park, while families love the fun splashing and slides of all shapes and sizes at Water Country USA!
Yorktown, Virginia
Nuzzling up its historic district with a two-acre beach frontage at the entrance of the York River into the bay, you bet Yorktown is breathtaking. From the architecture and old-world charm woven into the seascape beauty of Chesapeake Bay, Yorktown Beach is just a hop away, where the refreshing waters are perfect for boating, swimming, fishing, or just lounging efforts to absorb the breathtaking view and vitamin "sea." After beachcombing for unique shells, the Yorktown Trolley is a fun way to discover historic Yorktown on a heritage ride and spot out your stops, like the town's own Watermen's Museum.
From museums to restaurants and galleries, the American Revolution Museum is world-class, while market days offer a perfect opportunity to stock up for a picnic at the National Park Service picnic area. Back at the waterfront, slice the glittering estuaries of the bay via kayak or paddleboard with a rental from Patriot Tours & Provisions, or book a sailing charter and explore the York River. Visitors can enjoy a morning jog or a romantic rendezvous at sunset along the scenic mile-long pedestrian Riverwalk before dinner or drinks by the fishing pier or the Riverwalk Landing Piers, where you can dock your own boat.
Epitomizing the traditional, hard-working, yet laidback coastal lifestyle, the Chesapeake waters and rivers offer salty and fresh-aired outdoor opportunities. Having dazzled the seafaring Captain John Smith over four centuries ago, Onancock weaves a tapestry of old and new, with museums, cuisine, and art galleries peppering the vibrant downtown district.
Settled by the British, Crisfield is in a tight cultural embrace with the bay that visitors can discover through watersports, a unique local accent, festivals, and spectacular sunsets from the City Dock or the Cove Marina with a giant rubber ducky and 515 slips.
