Easton, Md., reemerges as historical, cultural, and culinary hot spot

The small, charming town of Easton, Md., and its surrounding farmlands along the eastern shore of Chesapeake Bay is where Harriet Tubman grew up in slavery and later returned to help others escape its binds. This mural illustrates her passion and journey.Pamela Wright

EASTON, Md. — This small, charming town and its surrounding farmlands along the eastern shore of Chesapeake Bay boast a rich, often dark heritage. This was once a hot spot for the Underground Railroad, a network of people, routes, and safe houses used to help enslaved people gain freedom. This is where Harriet Tubman grew up in slavery and later returned to help others escape its binds. These were also the childhood (and enslaved) stamping grounds of abolitionist Frederick Douglass, and the former Talbot County Jail in downtown Easton is where Douglass was imprisoned after a failed, early attempt to escape slavery.

Earlier this spring, archeologists discovered the location of the house where Tubman spent part of her childhood. That’s worth a trip!

We love history and visiting historical places, standing in the footsteps of important characters of the past. But we were also very intrigued by what is happening in Easton. This leafy, often-overlooked community (the harbor town of nearby St. Michaels steals most of the limelight on the Eastern Shore), is undergoing a massive renaissance, largely at the hands of one man. Paul Prager, principal of Bluepoint Hospitality, who attended the nearby Naval Academy and has a summer home and farm in the area, has been buying historic buildings in town, and opening a slew of new, upscale businesses. Through his passion for the area (and deep pockets), Prager is completely revitalizing and restoring the once down-and-out, distressed city into a cultural and culinary hub, bringing in top architects, designers, chefs, and sommeliers.

“I wanted some of the same things I enjoy in New York City,” said Prager, who also has a home and offices in NYC. “I thought if I created these places for me and my family and friends to enjoy, others would come. Besides, I needed something to do.”

Prager is doing that something on an epic, city-changing scale. His company, Bluepoint Hospitality, has bought and renovated several historic buildings, and opened 10 upscale businesses, including a coffeeshop, upscale food bazaar and salad bar, scotch and champagne lounge, fine dining restaurant, ice cream parlor and tea shop, an organic juice bar, an Italian market with a pasta and wine bar, a fine crystal, porcelain, and silver gift shop, a Roman-style pizzeria, and a bookstore. He also has a behind-the-scenes office, private dining areas, a massive wine cellar and an impressive cheese cave. He now owns properties reaching close to 50 percent of downtown and employs more than 90 people. Other plans (a hotel and/or inn and retail bakery) are brewing.

We were dubious of what some would call a massive, just-because-you-can vanity project. But the results are hard to argue. With the large influx of money and new businesses (Prager has also donated some $5 million to the town and community for a variety of other projects), Easton has turned around, and people are coming.

We arrived midday and stopped for lunch at Sunflowers & Greens, a lively, bright café-style salad bar with uber-fresh ingredients, including blackened ahi tuna and prime beef tenderloin and 31-month Prosciutto de Parma as protein toppers. After, we meandered downtown, past independent shops and restaurants (in addition to Prager’s establishments), along streets lined with fine homes. The Academy Art Museum has a nice collection of works by modern American and European masters, a performing arts center, and a year-round roster of educational programs and classes. Nearby is the historic Ebenezer Theater, recently renovated by Bluepoint Hospitality and now the rent-free home for Chesapeake Music, a nonprofit organization dedicated to bringing renowned jazz and classical musicians to the area. We visited the Frederick Douglass statue in front of the Talbot County Courthouse, which controversially stands steps from another honoring Confederate soldiers, and walked through The Hill neighborhood; founded in 1788, it’s one of the oldest free African-American neighborhoods in the United States.

The historic Tidewater Hotel is a popular place to stay in Easton.Pamela Wright

A late afternoon visit to Bonheur, a Coco Chanel-inspired ice cream and pie shop, was a must. Bonheur is French for happiness and the middle name of the famous designer, and this bright café with hand-painted wallpaper and fresh flowers exudes French elegance. On Fridays, they offer an elaborate, oh-so-chic afternoon tea.

That evening, we slipped into a corner table at The Stewart, a handsome, intimate Scottish-style lounge with a menu of more than 170 single malt Scotch whiskeys and more than 100 vintage champagnes. The intricately carved fireplace came from Europe; the Baccarat glasses are one-of-a-kind antiques. We sipped glasses of chilled champagne and enjoyed chips and dip: made-to-order potato chips topped with a smear of coconut and leek cream and Kaluga caviar. Dinner was at The Wardroom, a bright, open marketplace by day and dining space in the evening, serving fresh, house-made pasta and sauces, and a smart, curated selection of wines. We started with the pillowy, rich burrata, followed by fluffy, light gnocchi lightly doused in a rich, deep-flavored Bolognese.

Bumble Bee Juice, an organic juice bar, is one of the newly opened, upscale properties in buzzing downtown Easton.Pamela Wright

The next day, we hit the road, following the Harriet Tubman Byway, a self-guided driving tour covering around 125 miles with 36 historic sites (www.harriettubmanbyway.org). We visited the Linchester Mill, where free and enslaved African-Americans worked and most likely exchanged information about the Underground Railroad. We passed the Leverton House, a safe house along the railroad, and stopped at the Webb Cabin, a simple hand-hewn log home, where James H. Webb, a free African-American farmer, lived with his enslaved wife and their four children. We sleuthed out the site of the recent discovery of Tubman’s childhood home. In 2020, the US Fish and Wildlife Service acquired a 2,600-acre parcel of land that archeologists believed included the former home site of Ben Ross, Tubman’s father. In early 2021, artifacts and remnants from the household were discovered. Plans are now underway to include the site as part of the official Harriet Tubman Byway.

The centerpiece of the self-guided trail is the Harriet Tubman Underground Railroad State Park and Visitor Center, surrounded by the rolling farmlands, creeks, and marshes where Tubman once lived and worked under slave masters. The 10,000-square-foot museum contains exhibits on Tubman’s childhood and early adulthood spent in slavery, as well as her later years as a suffragist, civil rights worker, and humanitarian.

On our final night, we dined at Bas Rouge, Prager’s contemporary fine dining establishment, modeled after upscale European restaurants, with modern adaptations of traditional Viennese and European classics. The halibut ceviche was served with a delicate, fresh, and bright yuzu coconut. The Spanish octopus was perfectly grilled, accompanied with a fermented fresno and paprika mayonnaise and herb-y chimichurri. The fresh caught, local rockfish was served with sweet corn and saffron risotto.

Leafy, often-overlooked Easton is undergoing a massive Renaissance, emerging as a lively cultural and culinary hub.Pamela Wright

We chatted with a couple dining next to us, and eventually asked them what they thought of all the changes in Easton, and Prager’s growing empire and influence. “For us, it’s good,” the woman said. “He’s offering something we didn’t have in Easton and improving the downtown. I think it’s a good change.”

We can’t argue with the results. Charming Easton, midway between Washington, D.C., and New York City, is fast becoming a go-to destination.

For more information visit www.eastonmd.org and www.bluepointhospitality.com.