The best things to do, eat, and see

Easton, Maryland, is full of charm and history — Photo courtesy of Talbot County Economic Development and Tourism

Maryland’s Eastern Shore along the Chesapeake Bay is a playground for sailors, seafood lovers, and sunset chasers. Easton, Maryland, a charming, walkable town that punches well above its weight regarding cultural attractions and dining, is a must-stop. A short drive from Washington, D.C., Baltimore, and Philadelphia, Easton might not be on the water, like nearby St. Michael’s, but the coastal feel is there.

The town comes alive in the summertime when vacationers descend to enjoy the area’s waterways, villages, and local crab and oysters. But its history, charm, and colonial and Victorian architecture make this a year-round destination. No wonder it’s been a top contender for Best Small Town Cultural Scene and Best New Year’s Eve Drop in the USA TODAY 10Best Readers’ Choice Awards.

Here’s where to go, what to do, and where to stay in Easton, Maryland.

Things to do in Easton

The collection spans centuries at Easton, Maryland’s Academy Art Museum — Photo courtesy of Academy Art Museum

For a small town, Easton is rich in arts and culture. At the restored 100-seat Ebenezer Theater, celebrated musicians from around the world take the stage. The 400-seat Avalon Theatre hosts touring bands in an art deco venue a few blocks away.

Founded by a group of local artists in the 1950s, the Academy Art Museum features a wide-ranging collection, from Marc Chagall and Mary Cassatt to contemporary artists. The mix of 19th century and new architecture includes a beautiful two-story glass atrium. Catch special exhibitions that showcase works from modern masters and emerging artists alike.

Frederick Douglass is a beloved son of Easton, Maryland — Photo courtesy of Talbot County Economic Development and Tourism

Easton was involved in some meaningful moments in Black history, particularly those involving Frederick Douglass and Harriett Tubman, who were both born in this area.

Take self-guided driving tours of important moments in Douglass’ life, including the abolitionist’s early days on the Eastern Shore before he escaped enslavement and returned as a local hero.

Don’t miss the Harriet Tubman Underground Railroad Visitor Center, about 30 minutes south of Easton. This national park site tells the story of Tubman’s life, from the time of her enslavement in Maryland to her brave Underground Railroad missions and beyond.

Where to eat in Easton, Maryland

Bas Rouge in Easton, Maryland is led by a James Beard Award finalist — Photo courtesy of Sarah Maiellano

The ultimate destination on the Eastern Shore is Bas Rouge. Led by James Beard Award finalist Harley Peet and former staff from New York City’s Le Bernardin, Bas Rouge exudes elegance. Rare ingredients dot the prix fixe menu in this glowy, high-ceilinged space, while sommelier-led wine pairings complement each course. You must order post-dinner cheese and dessert, plated tableside from rolling trolleys.

Bonheur features ice cream and crepes in a beautiful space — Photo courtesy of Greg Powers

Bas Rouge’s sister eateries should also be on your list. Bonheur serves ice cream, pie, high tea, and morning crepes in a whimsical, picture-perfect space. Sunflowers & Greens specializes in fresh, create-your-own salads, some with high-end ingredients like savory prosciutto.

Locals enjoy tiki-themed Tiger Lily for brunch. For lunch, dining on the patio at Legal Assets, located in an 1867 carriage house, is a treat.

Who was voted the best?: Best Coastal Small Town (10Best Readers’ Choice Awards 2024)

Where to sample wine and scotch in Easton

The Stewart has the deepest whiskey and Scotch collection in Easton, Maryland — Photo courtesy of Sarah Maiellano

On the same block as Bas Rouge, The Stewart takes its cues from Edinburgh. Its $1.5 million Scotch collection is set behind a curved bar in a cozy space with a central fireplace. Your best bet is to try one-ounce pours of a few different single malts — the knowledgeable bar staff will guide you. The menu is tight, with indulgent treats like fries topped with caviar and a grilled cheese stuffed with braised short rib.

The Wardroom is a busy wine, liquor, and cheese shop and a sit-down restaurant. During the day, come for cheese (aged in a 40-degree underground cave on-site) and charcuterie-filled lunches, and at night, it’s all about fresh pasta. A self-serve wine tap system lets you sample well-sourced new and old-world wine.

Where to shop in Easton

Eclectic art hangs at Flying Cloud Fine Art Posters in Easton — Photo courtesy of Bluepoint Hospitality

All over town, large-format vintage posters decorate the walls of local businesses. Call it the Flying Cloud Fine Art Posters effect. This gallery and shop collects and sells colorful posters that hawk long-gone airlines and liquor brands. Next door, find bestsellers and a sweet children’s section at Flying Cloud Booksellers.

Stroll around to find art galleries and lovely shops of all stripes, like Caroline Dalton’s boutique, Arrae, known for fine jewelry, home decor, beauty products, children’s items. Get in the coastal spirit at Sailor, which outfits shoppers in Lilly Pulitzer, Southern Tide, Patagonia, Vineyard Vines, and other brands perfect for seaside locales. Shopping for kids is easy at Crackerjacks, where owner Linda Laramy has sold unique toys to generations since 1979.

Benjamin offers all the shiny things in Easton — Photo courtesy of Francine Zaslow

Benjamin is a must-stop whether you’re a window shopper or have the budget to collect fine crystal, china, and silver. The gallery-style boutique literally sparkles.

A quick drive from downtown, pick up some Amish-style soft pretzels, pies, and fudge at Easton Amish Market. More than 20 vendors from central Pennsylvania sell their wares — including solid wood furniture — at this market.

Who was voted the best?: Best Beach in the Northeast (10Best Readers’ Choice Awards 2023)

Where to stay in Easton, Maryland

Tidewater Inn is centrally located in downtown Easton — Photo courtesy of Talbot County Economic Development and Tourism

You can walk to all of Easton’s attractions from the Tidewater Inn. This centrally located hotel offers comfortable rooms in its main building and a historic mansion about a block away. Rooms take on distinct themes, like the Palmetto Suite and the French Suite.

The Hummingbird Inn, a bed and breakfast in an 1800s house, is also centrally located. Rooms here are spacious and guests enjoy gathering in a Victorian Garden with a fountain and a firepit.

For a next-level stay, drive 10 miles to the Inn at Perry Cabin in the buzzy neighboring town of St. Michael’s. You might recognize it as the waterfront filming location of the film, “Wedding Crashers.” Named the most romantic inn in the U.S. by 10Best readers, this luxury property features a spa, golf, tennis, sailing, and a popular seafood restaurant.