Drive time from NoVA: 3 hours and 15 minutes, plus 45-minute ferry ride
Outdoor enthusiasts will love escaping to these idyllic isles of the Chesapeake Bay, home to vibrant bird populations, fishing galore and plenty of kayaking. Spread out over 8,000 acres, Smith Island is a small archipelago defined by its three towns: Ewell, Rhodes Point and Tylerton. Only accessible by ferry, this island evokes an authentic small-town charm.
Where to stay
Options are limited to a few B&Bs and some rental homes. (Find a list at visitsmithisland.com/stay; some properties are available through Airbnb.com.) Susan’s on Smith Island Bed & Breakfast is a charming choice featuring first-rate hospitality, waterfront views and a hearty breakfast (dinner is available for $30 per guest). Situated in a picturesque mid-19th century Victorian, the Smith Island Inn offers guests complimentary use of its bicycles and canoes, as well as a charming breakfast spread.
Day 1
Morning
Hop the ferry to Smith Island. Several different operators depart daily at 12:30 p.m. from the dock at the end of Route 413 in Crisfield, Maryland. If you’re renting a home, do your grocery shopping on the mainland for the best selection and prices.
Afternoon
Have a late lunch at the Harborside Grocery and Restaurant, known for stellar seafood and a beloved cheesesteak. For dessert, stop at the recently revitalized Smith Island Bakery, which crafts the island’s namesake dessert, a towering treat interspersing nine thin layers of yellow cake with fudgy chocolate icing. There’s also a selection of handmade products by local artisans for sale. Learn about the island’s history, unique dialect and crabbing industry by visiting the Smith Island Cultural Center. Afterward, rent a golf cart or bicycle (available from the Bayside Inn Restaurant and elsewhere) to tour the island at a leisurely pace.
Evening
Savor seafood galore at Bayside Inn Restaurant, making sure to order its renowned cream of crab soup and whatever soft shell crab preparation is being offered. Or choose to stay in for the night. For an extra fee, many rental homes and B&Bs provide dinner, including buckets of steamed crabs. Whether you eat out or dine in, don’t forget to BYOB as the island is completely dry
What’s New
The recently revitalized Smith Island Bakery offers a variety of flavors of the iconic cake—including pineapple, coconut and lemon cream—alongside handicrafts from Bay artists. Many B&Bs and rental property owners have started offering steamed crab deliveries to guests for dinner. And don’t miss the Smith Island Cultural Center, which is always updating its information on the island’s rich history.
Day 2
Morning
Grab sandwiches, sides and drinks from Bayside Inn Carryout. Use a kayak (offered for free at many B&Bs or to rent at various locations) to explore the channels wending their way between the islands and the marshy coastlines. (A paddler’s guide of notable water trails is available at the cultural center for $3.) While you’re out, keep your eyes peeled for local birds, including herons, egrets and osprey.
Afternoon
Charter a boat for a fishing expedition, which might score you striped bass, trout or flounder. If that’s not your speed, there are sea glass hunting excursions along the shores and seaside hunts for Native American artifacts, including arrowheads and pottery shards. (A list of captains to guide you on these excursions is available at the cultural center—or just go down to Ewell’s pier and ask around.)
Evening
Cook your catch (upon request, some B&B proprietors and homeowners will prepare it for you) or catalog your finds as darkness falls.
Tip
In November, the islands become a temporary home to many wintering waterfowl. Visitors can expect to see a variety of duck species, including American black ducks and mallards.
Day 3
Morning
Take a trip to Tylerton. Though the town is only reachable by water, it’s easy to arrange passage on two local boats, the Captain Jason II or Captain Waverly Evans. Stop in at the Smith Island Crabmeat Cooperative to watch the ladies pick crabs and learn about the history of crabbing in the Bay.
Afternoon
Have lunch at Drum Point Market, making sure to order proprietor Mary Ada Marshall’s famous crab cakes. If you’re a passionate baker, she teaches classes on how to make Smith Island Cake. Afterward, book a boat over to the brown pelican breeding grounds, which makes for great birdwatching rich with excellent photography opportunities.
Evening
Head over to the neighboring town of Rhodes Point for the best sunset views on the island. Don’t forget to snap a pic for your Instagram, though you may have to wait until you’re home to post it, because cell reception on the island is spotty at best.
This post originally appeared in our September 2019 issue as part of the Weekend Getaways cover story. For more travel content, subscribe to our newsletter.