At 31 square miles, Kent Island is the largest—and nearest—island in the bay.
Do: Stop by the Chesapeake Heritage & Visitor Center (425 Piney Narrows Rd.; 410-604-2100), a museum/visitors center, to get your bearings, then walk or bike the 6.5-mile Cross Island Trail through woods and wetlands before ending at Terrapin Nature Park, with its patch of sand and great views of the Bay Bridge.
Eat: Kent Narrows is crazy with seafood restaurants, from venerable Harris Crab House (433 Kent Narrows Way; 410-827-9500) to the Jimmy Buffet-esque Jetty Restaurant and Dock Bar (201 Wells Cove Rd.; 410-827-4959).
Stay: You’ll get views of the bay, a spa, and a restaurant/outdoor lounge with live music on Friday nights at the new Inn at the Chesapeake Bay Beach Club (180 Pier 1 Rd., Stevensville; 410-604-5900).
Getting there: An hour from DC* via Route 50.
Home to about 275 hardy residents as well as a famous eight-to-ten-layer cake that’s become Maryland’s state dessert, Smith Island is roughly 91/2 miles west of Crisfield in the middle of the bay—a place so remote that CNN once dubbed it one of the best places in the US to drop off the grid.
Do: Get around like a local on a bike or a golf cart rented from the Bayside Inn (4065 Smith Island Rd., Ewell; 410-425-2771), then watch the women pick crabs at Smith Island Crab Meat Co-op (123 Wharf St., Tylerton; 410-968-1344).
Eat: The Bayside Inn has filling fried-seafood dinners. The restaurant also serves slices of Smith Island Cake, or you can pick one up to go from the Smith Island Baking Co. (718 Broadway, Crisfield; 410-425-2253).
Stay: Smith Island Inn (20947 Caleb Jones Rd., Ewell; 703-729-4462) is the spot to get away from it all.
Getting there: Several passenger ferries make the daily 45-minute voyage from Crisfield, a two-hour-and-45-minute drive from DC, or just during summer, from Point Lookout, an hour and 45 minutes from DC. See visitsmithisland.com/
This Patuxent River isle is a mecca for sailors and revelers headed to the storied Tiki Bar (85 Charles St.; 410-326-4075) for a mai tai or three.
Do: The Calvert Marine Museum (14200 Solomons Island Rd.; 410-326-2042) is an excellent introduction to the area’s culture and ecology. See river otters, check out a screwpile lighthouse, and go for a cruise on the Wm. B. Tennison, a former Chesapeake buyboat that dates to 1899.
Eat: CD Cafe (14350 Solomons Island Rd.; 410-326-3877) has a menu that ranges from Australian-leg-of-lamb sandwiches to “Bangkok scallops” in coconut curry. Finish your meal at Lotus Kitchen (14618 Solomons Island Rd.; 410-326-8469) for a slice of Kim’s Key Lime Pie. It’s the real deal.
Stay: Solomons Victorian Inn (125 Charles St.; 410-326-4811) is a circa-1906 Queen Anne right on Solomons’ harbor.
Getting there: It’s about an hour and 20 minutes from DC via Route 4.
“Crab City, U.S.A.” has been so isolated for so many years that many residents still speak with a version of an English accent.
Do: Learn about the island’s fascinating past at the Tangier Island History Museum (16215 Main Ridge Rd.; 757-891-2374). Paddle to the remote beach on the island’s south side. Chances are it’ll be just you and the birds.
Eat: Soft-shell crabs are an island specialty. Find them—and a menu full of other local seafood—at Fishermen’s Corner Restaurant (4419 Long Bridge Rd.; 757-891-2900).
Stay: The Bay View Inn (16408 W. Ridge Rd.; 757-891-2396) has seven cottages and two rooms in one of the oldest houses on the island.
Getting there: Several passenger ferries make the daily 14-mile trip from Crisfield, a two-hour-and-45-minute drive from DC. Alternatively, the Chesapeake Breeze departs daily from Reedville on Virginia’s Northern Neck, a two-hour-and-40-minute drive from DC, through October. See tangierisland-va.com/
This island, about three miles long, is the blue-collar cousin to posh St. Michaels, which lies separated by a drawbridge 14 miles up the road.
Do: Get the 411 on island life at the Tilghman Watermen’s Museum (6031 Tilghman Island Rd.; 410-886-1025), then join a real waterman on his boat. Captain Wade Murphy gives tours aboard the Rebecca T. Ruark (410-886-2176), the oldest skipjack on the bay.
Eat: Two If by Sea (5776 Tilghman Island Rd.; 410-886-2447) has the best breakfasts on the island and serves up homey dinners on Friday and Saturday nights. Hit the Tilghman Island Country Store (5949 Tilghman Island Rd.; 410-886-2777) before dinner for a winetasting or after for a hand-dipped ice cream.
Stay: The end-of-the-road Black Walnut Point Inn (4417 Black Walnut Point Rd.; 410-886-2452) has eye-popping views where the Choptank River meets the bay.
Getting there: It’s an hour and 50 minutes from DC via Route 50.
*All distances are measured from the Washington Monument.
This article appears in our July 2016 issue of Washingtonian.