Maryland’s Most Charming Town Is Where Big City Cool Meets Small Town America

From quaint bookstores to contemporary fine dining, Easton has the best of both worlds. 

Federal Street, Easton, Maryland
Photo: Eric Taylor

Initially, Easton resembles other towns in Maryland’s Eastern Shore. The population is just shy of 17,000 residents, with well-preserved historic buildings hugging the narrow, tree-lined streets. And naturally, the pace is unhurried.

But one block downtown on Federal Street stands out. The businesses here, which range from a boutique selling elegant European dinnerware to a cold-pressed juice bar, vary concept-wise, yet feel familial with their polished design, warm service, and curated offerings. And that’s because they’re all part of Bluepoint Hospitality, a family of restaurants and shops envisioned by Paul Prager. While he’s a self-proclaimed “Brooklyn guy who went to the Naval Academy,” he’s also the CEO of Beowulf Energy — and a person whose affinity of Easton and hospitality runs deep.

Bas Rouge Dining Table
Nicole Franzen

The longtime New Yorker fell for the town’s subtle charms fifteen years ago, because he wanted his family to be “surrounded by nature and near the water, but not be in the Hamptons.” Though Prager appreciated the quality of life Easton afforded him, he missed his social life back in Manhattan. “I love to go out and eat, and appreciate every aspect of it, from the crystal a wine is poured in to the furniture,” he says.

Things started clicking together when he purchased a row of distressed buildings on Federal Street back in 2008, and later founded Bluepoint Hospitality to create places that, in his words, “make me feel at home” while supporting the local community. Also important was respecting establishments that were already open. “We don’t ever want to compete with them,” explains Prager, who’s adamant about developing spots that only enrich and diversify Easton.

Sunflower and Greens dining table in Easton, Maryland
Nicole Franzen

Sunflowers & Greens, for example — opened in 2013, it was Bluepoint’s first concept — filled the need for an everyday salad bar, and stood out from fast-casual chains by prioritizing quality ingredients (think Russ & Daughters’ smoked salmon, made-from-scratch dressings, and seasonal greens), and presenting them on delicate French Bernardaud plates. In 2016 and a few doors down, Prager unveiled Bas Rouge, a fine dining restaurant turning out contemporary European cuisine by Executive Chef Harley Peet in a polished dining room dripping with a Lobmeyr chandelier and nineteenth-century German art. The menu and setting may skew formal, but the service is refreshingly relaxed — not unlike Le Bernardin, a favorite of Prager’s. (Coincidentally: Ben Chekroun, Le Bernardin’s front of house manager for 27 years, recently joined Bluepoint Hospitality as General Manager of all operations.)

Waitress walking out of The Wardroom
Melanie Dunea

Like its siblings, the two newest additions to Bluepoint — both opened over Labor Day weekend — seamlessly fit into Easton’s social fabric. Occupying a former hotel, The Wardroom is a retail gourmet shop during the day that transforms into a lively gnocchi and wine bar at night. (You can self-serve from 25 bottles kept at the proper drinking temperature in state-of-the-art Enomatic dispensers.) And Flying Cloud Booksellers harkens back to the quaint, neighborhood stores many of us grew up with. The cozy space is accented with vibrant paintings by Penelope Gottlieb, and stocked with thousands of carefully chosen books, with an especially strong selection of children’s literature.

And in contrast to restaurateurs who let employees go during the pandemic, Prager stood by his principles — even if it meant losing money indefinitely. “I knew the situation could hurt a lot of people, and the last thing I wanted to do was contribute to it,” he recalls. “This was the time to focus on our team, not just financial returns, and keep everyone together during these challenging times.

Thankfully, trusting his intuition paid off faster than he anticipated. Not only did the Easton community rally around Bluepoint’s businesses even more than pre-COVID, travelers beyond the Chesapeake Bay started visiting Easton to experience Bluepoint’s uniquely human-centered approach to hospitality. “We’ve had record numbers despite limitations like reduced occupancy and shorter hours,” says Prager, who’s always implicitly understood the key to success isn’t just the bottom line — but loyalty to the people who help build you up.

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