Downtown Easton attractions are walkable. (Photo by Mark Sandlin)
As I drove across the Chesapeake Bay Bridge en route to Easton one Saturday morning in late October, I was prepared to encounter some sort of posh, water-nestled enclave of New Money. Last summer, after Easton made it onto Kiplinger’s list of small towns with the highest concentration of millionaires in the U.S. — some 7.4 percent of its roughly 16,000 households command seven-figure lifestyles — the town became the subject of a write-up on Forbes magazine’s website: Easton and its nearby cousin municipalities of St. Michael’s, Oxford and Trappe were dubbed the “new Hamptons.” Its proximity to Washington, D.C., which is about 90 minutes away by car, and the fact that it’s situated in Maryland (the state with the highest number of millionaires per capita) makes the comparison an alluring one. But Easton actually is more nuanced, a blend of affluence and ancestry.
Friends Meeting House (Photo by Mark Sandlin)
Walk Through History
Easton was founded in 1710, but its history stretches further back. Friends Meeting House, established by Quakers in 1682 on South Washington Street, is reputed to be the oldest framed house of worship in the country. Less than a five-minute walk away — everything about Easton is eminently walkable — is The Hill, a neighborhood that may have been America’s first community of free blacks.
The census of 1790 recorded 410 free African-Americans living on The Hill, and descendants still live there. It’s an astonishing number, given Maryland’s history as a slave state, but also when considered alongside the 346 blacks enslaved at the Wye House Plantation, a short drive from Easton’s downtown, where Frederick Douglass spent his childhood before escaping to freedom. A statue of the great abolitionist and speaker was erected in 2011 at the Talbot County Courthouse on North Washington Street.
Avalon Theater (Photo by Mark Sandlin)
Food and Fun
When you tire of walking, get a caffeine boost at Rise Up Coffee Roasters, original to the Eastern Shore. For lunch, options abound, but the roasted apple and blue cheese salad — complete with sliced beef tenderloin for $16 — at Sunflowers and Greens will leave you satisfied.
Afterward, head back to the epicenter of town for the requisite shopping stops. Several antique stores are sprinkled throughout. At Tharpe Antiques and Decorative Arts, I found several books on the Civil War for my history-buff parents for under $30. Berrier Ltd. is the shop where men interested in looking the part of a New Hamptons swell can find quality clothes; for women, both Andrea’s Papillon and swank. are close by. Downtown Easton’s shopping scene along Dover and Harrison streets is also near its cultural attractions. The Academy Art Museum holds a craft show each October. The Avalon Theatre, an Art Deco gem, programs an eclectic mix of musical and stage performances.
For dinner, a meal at the Bartlett Pear Inn will let you know what it’s like to eat where the politicos do (former Vice President Dick Cheney has dined here). Tidewater Inn is a great option for an overnight stay. It plays host to weddings and other celebrations, but for my money, the real draw is the collection of wooden rocking chairs along its patio. On an unseasonably warm late-October afternoon, a beer from the Tidewater’s bar was the perfect complement.
When to go
Typically, the time to hit the Eastern Shore is from spring through fall. That’s when the big events like the Monty Alexander Jazz Festival, held over Labor Day weekend, and October’s Chesapeake Film Festival take place.
Historic walking tours
Take a self-guided tour and move at your own pace. The Talbot County Visitor Center in Easton has the maps you need to walk around the town.
