1 hour, 30 minutes
When people think of Maryland’s Eastern Shore, the Hamptons-esque glitz of St. Michaels usually comes to mind. That is, until nearby Easton, which sits at the source of the Tred Avon River, began charming travelers. It’s a jumping-off point to neighboring shorefront towns and offers a romantic respite for couples, particularly those with a penchant for luxe but laid-back living via fine cuisine, curio-filled boutiques, galleries, outdoor activities, and a movie-script setting. Case in point: Fay Wray and Gary Cooper reportedly filmed The First Kiss, one of the last silent movies, in the enclave.
Much of the hamlet’s development—and resurgence—can be credited to energy mogul Paul Prager and his Bluepoint Hospitality Group, which has been opening a range of restaurants and shops here since 2013. The latest: Roma Alla Pala, a takeout-only pizzeria that bowed in February and is, in Roman tradition, scissor-cutting square pizzas with crusts that take 72 hours to make from its tiny brick-clad space. In the fall, the group debuted The Wardroom, a gourmet market, and Flying Cloud Booksellers; it is also updating a few of its other projects.
A non-Bluepoint venture in the works is Josef’s of Easton, a cheesecake/cupcake side project from Gregory James—the executive chef over at the Inn at Perry Cabin—who is currently scouting locations around town. (The family biz is named for his father and nods to his brother’s sweet shop in Wisconsin.)
There’s a new hotel spa and an outdoor tented pavilion created in partnership with the iconic Avalon Theatre and NYC heavy-hitter Electric Lady Studios (part of The Weeknd’s After Hours was recorded here) to accommodate musical acts amid the pandemic. Oh, and as for the waterfront? A years-long redevelopment is under way to modernize the largely industrial spot with a potential riverfront park, green space, boathouse, and more.
By the beach
Here, it’s all about communing with nature, and there’s ample opportunity to do so. Talbot County has 600 miles of waterways and 27 public landings. Head to Easton Cycle & Sport to borrow kayaks and stand-up paddleboards (and pup-friendly iterations by locally run Paddle Dog Boards) and to get recommendations from owners Ryan and Julie Hickey. The vessels can be delivered to your hotel or rental, as well as to Easton Point on the Tred Avon. If you’re a strong paddler, try the full-day, out-and-back trip to Oxford; otherwise, Dixon and Peachblossom creeks are much easier paddles from town. Spend a tranquil afternoon at the waterfront Bill Burton Fishing Pier State Park in Trappe; there’s also a small strip of sand in Oxford at The Strand and the Bellevue and Claiborne landings.
Be sure to pick up a nutrient-packed lunch from Sprout Café, where everything is made from scratch, as well as a light read from the new Flying Cloud (there are some 10,000 titles from which to choose). Or simply watch the sailboats and yachts cut along the bay. Even better? Charter your own. Multiple operations in the surrounding area offer private tours. Experience a splash of St. Michaels life via the Inn at Perry Cabin: Its exclusive sailing charters are available to non-guests. Sail Selina II will take you out for half-day, sunset Champagne, and moonlight tours for a starry night on the Miles River aboard the largest surviving vintage catboat.
Biking along the Eastern Shore is practically a requirement, so spend a sunny morning spinning your wheels. The classic 30-mile trek from Oxford to St. Michaels will have you pedaling through Easton’s sister cities, riding the ferry across the Tred Avon, and viewing historic sites. Look out for the cannonball circa the War of 1812 lodged in a tree near the Royal Oak post office. Back in town, explore the area’s rich cultural history at the Frederick Douglass statue honoring his birthplace; a Juneteenth celebration commemorates abolition.
The annual Plein Air Festival is scheduled to resume in July, during which artists will paint the world around them. There are antique shops galore; the Modern Bulldog is our pick for midcentury kitsch like rainbow-hued Danish candlesticks. And the food is not to be missed. Stroll to the fashionably whimsical Bonheur, inspired by Coco Chanel, for small-batch ice cream like lemon basil.
In the mood for romance? Consider a prix fixe dinner at the recently expanded Bas Rouge, a polished homage to modern European fare. Cap it all off with a parting cup at The Wardroom, which transforms into a wine and gnocchi bar by night. Executive chef Harley Peet slings pillowy clouds of the pasta (get the caviar if it’s available) to team with tastings from the Enomatic dispenser. The rarest bottles are stored in a vault discovered during the 19th-century building’s renovations. And you must order a fromage plate curated by cheesemonger Rita Felgar. She’ll create a selection according to your taste—something mild and creamy, something aged between eight months and two years, and something blue.
There are benefits to wherever you hang your sun hat, from quaint B&Bs to rentals. The Tidewater Inn puts you in the heart of it all. The premier room and suite updates were finished last year, but a room in the 1870s-era Tidewater House, about a block from the main establishment, simply delights with a gorgeous glass-encased lounge and themed decor in each room. The blue-clad French iteration takes Francophilia to another level and has touches like gold-cherub bathroom fixtures. An onsite spa opened last summer. The Lovers’ Package treats you and your partner to a body polish, foot treatment, and massage; ask about the Wednesday discount for teachers and parents who’ve been educators. Other perks include a cozy tavern and a van to shuttle you to St. Michaels for a voyage on the Patriot Cruise. Rather rent? We’re smitten with the corn crib turned sleek Airbnb in the St. Aubins Heights neighborhood.