Kir Tuben Photography
Considering a coastal wedding, but overwhelmed by the options? These scenic Maryland towns have a sense of place that will anchor your whole celebration. Just ninety minutes east of BWI, Maryland’s Eastern Shore is brimming with beauty, history, and waterfront culture—all on a cozy, small-town scale. The only question is “Which town?” to have and host you. Better add “road trip” to that planning checklist.
Easton
The “cultural capital” of the Eastern Shore, Easton buzzes with upscale boutiques, a vibrant arts scene, and an epicurean takeover courtesy of the ubiquitous Paul Prager. Settled by Quakers in 1682, this destination’s sleepiest years seem behind it, though the horse-drawn carriage tours remain.
Miles from BWI: 62
Size: 11.5 mi2
See & Do: Catch a show at the Avalon Theatre, sip rare scotch at the Stewart, view works by Rembrandt and Mary Cassatt at the Academy Art Museum
Eat: Crab cake wellington at Bas Rouge, the “Peach” pastry at P. Bordier Crêperie and Patisserie
Marry: The Tidewater Inn
Saint Michaels
Founded in 1661, this tony shipbuilding spot is known for antique shopping, cycling, and seasonal festivals. Though its tiny, it packs a punch, with elegant restaurants, charming churches, and a bevy of Colonial, Federal, and Victorian homes to admire.
Miles from BWI: 72
Size: 1.3 mi2
See & Do: Learn about oystering at the Chesapeake Bay Maritime Museum, sample spirits at the LYON RUM Distillery, tour pre-war automobiles at the Classic Motor Museum
Eat: Scallops a la plancha at Ruse & caramel cold brew ice cream at Justine’s
Marry : Inn at Perry Cabin
Cambridge
Wildlife and water sports are part and parcel of this 17th-century port town, which is situated on the Choptank River, 12 miles north of Blackwater National Wildlife Refuge. Our best Instagram tip — don’t miss the many murals (16 and counting) that depict everything from civil rights activists to birds in flight.
Miles from BWI: 78
Size: 13 mi2
See & Do: Enjoy a pint at RaR Brewing, honor the work of a hero at the Harriet Tubman Underground Railroad Visitor Center, take a guided kayak tour with Blackwater Adventures
Eat: Breakfast at Black Water Bakery
Marry: Hyatt Regency Chesapeake Bay
Chestertown
With an annual Boston Tea Party-inspired protest and a bronze statue of the former town goose — Chestertown has and always will be an eclectic connoisseur of history. Once Colonial Maryland’s second-largest city, Chestertown’s present-tense is decidedly non-fussy; an appealing mix of mom-and-pop shops, idyllic cobblestone streets, and 18th-century buildings perched along the Chester River.
Miles from BWI: 70
Size: 2.9 mi2
See & Do: Cruise aboard the Chester River Packet, visit the Saturday morning farmer’s market, find your way to Zelda’s Speakeasy if the light is green
Eat: Everknots at Evergrain Bread Company
Marry: Brampton Bed and Breakfast Inn & Brittland Manor
Tilghman Island
Sitting at the southernmost tip of Talbot County, this quiet watermen’s village overdelivers with its low-key feel and natural beauty. Those who relish off-the-beaten-path adventures will enjoy the serene simplicity of Tilghman life.
Miles from BWI: 85
Size: 2.8 mi2
See & Do: Explore the Bay by paddleboard, tour the Tilghman Watermen’s Museum, organize a fishing or duck-hunting excursion
Eat: Local oysters at Tickler’s Crab Shack, a spinach omelette at Two If By Sea, the daily special at Tilghman Island Country Store
Marry: Wylder Hotel Tilghman Island
CONSIDERATIONS
While the Shore’s charms are undeniable, its erratic weather, bridge traffic, and limited transportation options can be vexing to unprepared out-of-towners. Make sure your guests plan ahead, with these tips from local planners:
Book a room in-town (not across the bridge)
“Anyone coming to a wedding from across the Bay Bridge should plan to stay close, especially during summer wedding season. Otherwise, the traffic will be guaranteed horrendous.”
—Sarah Postles, lead designer for Ellie Belle Events
Organize transportation ahead
Ride-sharing services, like Uber and Lyft, are virtually nonexistent on the Shore, Postles says, so guests should consider renting their own cars and couples should consider providing shuttle transport. Some of these spots, like Easton and St. Michaels, are walkable; others, like Cambridge and Chestertown, may require more support depending on the weekend’s itinerary.
Prepare for the weather
“One of the biggest challenges we face on the shore is weather. From strong winds to scattered storms, always have a plan B in mind.”
—Melissa Candolfi, owner of Belle of the Ball Weddings & Events
