Get To Know Easton, Maryland

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Maryland’s Eastern Shore is a quintessential getaway for sailing, sun sets over the Chesapeake, and nautical flair. Posh Saint Michaels has all that in spades, but in recent years, Easton has put up a little friendly competition for the title of Talbot County’s best dining destination. The small town, remarkable for its picturesque downtown with brick sidewalks and historic architecture, outdoes itself when it comes to dining out. That’s in large part due to the efforts of Bluepoint Hospitality, which leads with an “if you build it, they will come” mentality. Founder Paul Prager, who made his fortune in the energy business, went about opening tasteful restaurant after tasteful restaurant here, enlisting talent from the likes of New York’s three-MICHELIN-star French restaurant, Le Bernardin. Take a journey through the 20 wine regions within Italy paired with handmade pasta at the newly reimagined The Wardroom. In between meals, art galleries and boutiques await.

Best Places to Eat, Drink, and Explore

Best Alfresco Dining: The Ivy

A brick-lined courtyard featuring a striped awning and greenery including ivy (naturally) is a charming setting for sandwiches and salads or cocktails like cranberry crushes.

Bluepoint Bonheur Tea Courtesy of Bluepoint Hospitality — Bonheur

Best Coffee Shop: Rise Up Coffee Roasters

The Eastern Shore’s favorite caffeine source roasts all its coffee in its Easton location—and sells very cool merch in addition to lattes. Grab a bite with your coffee like the Happy Cow vegan burrito or bacon, egg, and cheese on a scratch-made biscuit.

Best Fine Dining: Bas Rouge

Gracious service and a sophisticated menu that riffs on European traditions (think pastry-enveloped crabcake Wellington) are calling cards for this white-tablecloth establishment, which offers three- or four-course prix fixe menus.

Best Place to Raise a Pint: Washington Street Pub

This Easton classic recently made a comeback under the Bluepoint Hospitality banner, decked out with a handsome new bar that feels like it’s been there forever. Post up in a leather booth for fried chicken and a round from local brewery RAR.

Best Sweet Treat: Bonheur

Ice cream or pie? It’s a tricky decision at Bonheur, which scoops up flavors like coffee toffee crunch and slices like chocolate mousse. The sweets shop looks just as pretty as its desserts, thanks to hand-painted Gracie chinoiserie-style wallpaper.

Best Happy Hour: Legal Assets

From spritzes to espresso martinis, Legal Assets takes cocktails seriously. The restaurant is all in on happy hour, which stretches from 11:30 a.m. to 5 p.m. on Saturdays.

Claim to Fame

Chef Harley Peet

Bas Rouge executive chef Harley Peet is the Eastern Shore’s first-ever James Beard Award winner, earning the Best Chef: Mid-Atlantic title in 2024. Peet, who sails in his free time, uses both European delicacies and hyper local ingredients to create Bas Rouge’s elegant dishes— from fish plucked from the Chesapeake to tomatoes grown in a backyard garden. Peet’s culinary sensibilities touch all of Bluepoint Hospitality’s restaurants, from salads at Sunflower & Greens to slices of pizza at Roma.

Bas Rouge Dinner Scene Courtesy of Bas Rouge jpg — Bas Rouge

Where to Shop

Welcome Home

Need an oyster plate or oyster knife to bring home as an Eastern Shore souvenir? Downtown shop Welcome Home has it covered, along with tasteful French table linens and all sorts of cooking and baking equipment like de Buyer crepe pans.

Curlicue

Funky crab tea towels, pretty cloth napkins, and intriguing cookbooks (like How to Cook the Finest Things in the Sea [Artisan, 2025]) make Curlicue another shop downtown that’s worth perusing for home chefs.

Market at Dover Station

If you prefer the thrill of the hunt, the Market at Dover Station is packed with antiques and vintage finds meant for entertaining. The vendors within this
historic building’s walls sell everything from handwoven baskets to artsy cocktail glasses.