Why This Maryland Eastern Shore Town Should Be on Your Summer Trip List

Easton has a varied dining scene, dynamic history, and beautiful scenery—plus plenty of crabs.

Eastern Shore Maryland

The charming town of Easton has undergone a transformation in recent years.

Photo by Melanie Dunea

It’s hard not to think about crabs when someone mentions Maryland’s Eastern Shore, the peninsula extending hundreds of miles between the Chesapeake Bay and the Atlantic Ocean. Sometimes things like sailing, Old Bay seasoning, Smith Island Cake, or other seafood might also enter your mind. But most people won’t think of fine dining, chic European-influenced shops and cafés, and perfectly manicured gardens. Yet this is the town of Easton, Maryland, in 2022 in a nutshell.

It hasn’t always been this way. A small town in Talbot County east of St. Michaels, Easton was first established in 1710 as a place for the region’s courthouse and governmental offices and was known then as Talbot Courthouse and as the “East Capital” of Maryland. Easton had the Eastern Shore’s first bank, its first newspaper, its first federal offices, and its first brick hotel. The still-standing courthouse is also, unfortunately, the place where Frederick Douglass, who was born and enslaved nearby, was jailed for a week in 1836. Other historic buildings include the Tidewater Inn, which has been an inn for more than 200 years, the circa-1921 vaudeville house that is now the Avalon Theatre, and the 1820 schoolhouse that is currently home to the Academy Art Museum. But over the centuries, many buildings became dilapidated.

Recently though, Easton has been putting itself on the map once again. Going well beyond crab shacks, stylish new businesses—fine dining restaurants, Roman pizzerias, shops selling Austrian crystal and silver—are housed inside carefully restored historic buildings. There is an air of Hamptons-style sophistication (minus the attitude). And since the pandemic, it’s been flooded with weekenders and people who recently bought vacation homes or moved in full time during the pandemic, coming from D.C., Philly, and New York City. One person is behind much of this renaissance: Paul Prager of Bluepoint Hospitality.

Eastern Shore Maryland Bas Rouge

Grilled wild shrimp is on the menu at Bas Rouge.

Photo by Nicole Franzen

How Bluepoint Hospitality became a major Easton presence

Originally from New York, Prager, founder of multibillion-dollar infrastructure holding company Beowulf Energy, fell in love with the area after attending the Naval Academy in nearby Annapolis; eventually, he and his wife purchased a farm in Talbot County as a second home. They relocated there permanently from Manhattan during the pandemic. Although Prager loved the Eastern Shore, he also missed being able to easily access his beloved NYC restaurants like Le Bernardin and Marea.

“Maryland has always represented an escape for its natural beauty and serenity, but admittedly there were certain cultural offerings and a level of sophistication that we missed from city life,” says Prager. “It’s no secret that my primary passion is food, so I started there.”

He began purchasing empty buildings on Federal and North Washington streets in the 2010s, carefully restoring them, and so far has opened 10—and counting—retail and hospitality businesses under the Bluepoint Hospitality umbrella. He also restored the Historical Society Auditorium—now renamed the Ebenezer—which became the permanent home for Chesapeake Music, a group that brings chamber music concerts to the Eastern Shore. He also partnered with award-winning pianist Gabriela Montero for an artist-in-residency program there.

New York–based interior designer Shaun Jackson originally visited Prager in Easton about 10 years ago. “There was nobody around this town. Most of these lovely storefronts were empty or shut down,” says Jackson. In 2015, the two designed and opened a chic salad café and juice bar—Sunflowers & Greens and Bumble Bee Juice—both of which became extremely popular during the pandemic.

Further up the street is Weather Gage, a marble-clad nautical themed coffee shop; the Stewart, a plush lounge serving premium scotch and champagne; and the jewel-in-the-Bluepoint-crown, Bas Rouge, a Viennese-inspired fine dining restaurant with dishes like lime-cured yellowtail amberjack with caviar, white asparagus soup, jumbo crab cake, and a classic wiener schnitzel. Around the corner is pasta and wine bar/European market and wine shop the Wardroom, and nearby is the appealing bookstore and vintage poster shop Flying Cloud Booksellers and pizza joint Roma. Another can’t-miss spot is what might be the chicest ice cream and pie parlor in the country, Bonheur.


Easton is home to tiki bars, taco joints, and the all-important ice cream shops.

Photo by Greg Powers

“I was kind of thinking about Eloise at the Plaza, a fun and elegant place to come have an ice cream sundae,” says Jackson, who designed the whimsical yet fashionable shop. This meant commissioning intricate floral wall coverings from Gracie Studio, the revered company that creates hand-painted wallpaper found in places like the White House, adding detailed wainscoting, installing midcentury modern furniture, and ensuring there’s always a fresh bouquet of flowers on the counter (a Bluepoint hallmark). On the menu are a variety of delicious handcrafted ice creams, pies, and a refined tea service on Friday afternoons.

A top-notch team of locals, including the group’s executive chef Harley Peet (previously of the luxury hotel Inn at Perry Cabin in nearby St. Michaels) and head baker Glenn May, complement the New Yorkers.

The newest New York addition is celebrated baker Melissa Weller (previously of Per Se and Sadelle’s). She now makes the pies and other pastries at Bonheur and is in charge of the dessert menu at Bas Rouge, where she introduced a cake trolley that rolls through the dining room with her creations, which include a Sacher torte and orange almond poppy seed cake.

“These spaces that [Prager] has built out are incredible, just fantastical,” says Weller, who now splits her time between Brooklyn and Easton. “And the town itself is so quaint and I like the southern hospitality a lot—everyone’s polite, friendly, and gracious.”

Weller lost her job during the pandemic and Easton represented new opportunities. “I think that with the exodus from cities following the pandemic and resulting restaurant closures, Easton represented the same opportunity for hospitality professionals that it did for me years ago—a chance to create something new,” says Prager.

Obviously, the whole thing is also a little odd—Prager now owns about 50 percent of the town. And not everyone in Easton is a fan of his. After all, he’s an outsider who came in and transformed a good part of the town. Most of his businesses charge higher prices than most residents were accustomed to, in comparison to other local restaurants. But he and his company have also helped the town in many ways.

“Beyond providing dining and retail venue and employment to Talbot County residents and utilizing the multitude of nearby small farms, fishermen, and poultry and livestock producers, we are locally active and philanthropically committed,” says Prager.

“Easton hasn’t changed that much in the past 10 years, and that’s what I like about it,” says Cassandra Vanhooser, director of Economic Development and Tourism, Talbot County. “There are some legacy stores and some newcomers. There’s great history here, but it’s a community of forward-thinking, philanthropic individuals. The town itself is the attraction. It has the amenities of a city with the soul of a small town. [Bluepoint Hospitality’s] businesses and cultural attractions add the color and texture to an already beautiful tapestry.”

Easton beyond Bluepoint

Although Bluepoint’s presence in Easton is inescapable, there are plenty of other businesses worth visiting, including several other new restaurant openings and a few standbys.

There’s northern Italian spot Scossa, opened in 2019 by chef/owner Giancarlo Tondin, who worked at the legendary Harry’s Bar in Venice in the 1980s and helped open the original Cipriani in New York. Last year, tiki bar/taco joint Tiger Lily launched, bringing craft cocktails and an eclectic menu. Plus, longtime Mediterranean staple Out of the Fire will be moving to a new space in the coming months, and the Bagery, a veteran-owned from-scratch, organic bagel shop has become a regional standout. Crab Shack is as classic as it sounds, and the Easton Amish Market, with more than 20 vendors, including furniture makers, produce farmers, and bakers, is a must.

Beyond food, it’s worth browsing shops like women’s designer clothing store Dragonfly Boutique; home furnishing store Wye New; home goods store Dwelling & Design; and art galleries Trippe Gallery and Troika Gallery. Be sure to visit the Talbot Historical Society to discover the rich history of the area and the Academy Art Museum inside the circa-1920 schoolhouse, where you can view American and European masterworks. Take in the scenery on one of the trails in the 410-acre Pickering Creek Audubon Center, which is a working farm and home to vast wetlands.

In the end, Easton has both the historic significance and modern-day amenities that make it a fascinating and fun getaway.

“Easton has great architecture and a rich history as a modern municipality,” says Prager. “My vision was—and remains—to restore its original vibrancy by creating opportunities for young people with great schools, more residences in town, and a rich arts scene.”

Devorah Lev-Tov is a Brooklyn-based food and travel journalist who has been published in the New York Times, National Geographic, Vogue, Bon Appetit, and more.
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