Allegany County, Maryland
The gentle mountains of western Maryland give you all the cozy winter feels.
Why now: Follow the George Washington Trail, tracing the first president’s footsteps from young surveyor to president.
Do: Take in the area’s natural beauty aboard a vintage passenger car run by the Western Maryland Scenic Railroad. Sample local craft beer, wine, and spirits at the Toasted Goat, a sweet little speakeasy.
Stay: Expect quaint rooms, fabulous views, and a stellar breakfast at Town Hill B&B. The inn sits along the peaceful Historic National Road, America’s first federal highway and the brainchild of President Thomas Jefferson. With mountains on one side and water on the other, Rocky Gap Resort is smack dab inside one of Maryland’s most popular state parks. And you don’t need to hit the casino to enjoy the property; there’s also a spa, several restaurants, and a nightclub.
Talbot County, Maryland
This Eastern Shore design hub favored by East Coast decorators will inspire your home refresh.
Why now: The First Ladies’ Sale at Bountiful slashes everything in its high-end collection of furnishings and decor by 50 percent over Presidents’ Day weekend. Check out artsy ice sculptures and live music at the Chesapeake Fire & Ice Festival.
Do: Shop more than a dozen home furnishings and design stores. Find industrial pieces, neon signs, and Brazilian cowhides at Iron Will Woodworks. Mad Men-era cocktail shakers and groovy space-age chairs make Modern Bulldog a mid-century mecca. And limited-edition, 24-karat gold-rimmed porcelain plates emblazoned with the Eastern Shore’s beloved blue heron are on offer at Benjamin.
Stay: The Wildset in St. Michaels is a hip historic hotel with a firepit out back and a trendy restaurant with shareable plates up front. The Tidewater Inn in downtown Easton with its buzzy lobby bar has recently unveiled premier rooms with decorative details like Restoration Hardware fixtures.
Brandywine Valley
Embrace an elegant winterscape amid one of America’s greatest horticultural treasures.
Why now: Longwood Garden’s current installation Winter Wonderland features a grand conservatory with hundreds of orchids, while 400 outdoor acres pop with yellow and orange with witch hazel and other winter berries.
Do: At Longwood Garden’s Cafe you can warm up with a cup of local mushroom soup—after all, the area is known as “the mushroom capital of the world.” Idle an afternoon away at Pennsbury-Chadds Ford Antique Mall, where you’ll discover vinyl records, dinosaur eggs, and vintage rhinestones, among other treasures tucked into more than 100 dealer booths.
Stay: The stylish Hotel Dupont in Wilmington has recently launched a gorgeous restaurant called Le Cavalier that spins novel takes on French classics. Working fireplaces are a romantic touch in rooms at The Inn at Grace Winery, which is owned by Grace Kelly’s nephew and showcases tons of the icon’s memorabilia.
Colonial Williamsburg, Virginia
Experience a thoughtful modern approach to African American history.
Why now: Colonial Williamsburg has amped up its celebration of Black History Month with interactive exhibits, lectures, and live shows that reflect the important contributions African Americans made to the founding of the United States.
Do: Check out one of America’s largest collections of folk art, including a significant collection by African American artists. Try a cup of creamy peanut soup inside one of the paneled dining rooms at the recently renovated 18th-century King’s Tavern.
Stay: Dogs are welcome at the luxurious Williamsburg Inn, a refreshingly unfussy hotel on the property of historic Colonial Williamsburg. Kingsmill Resort’s family-friendly cottages along the James River have fireplaces, kitchens, and, during the month of February, are half-price.
Charlottesville, Virginia
Sip wine while tracing President Thomas Jefferson’s footsteps through the Piedmont countryside.
Why now: Jefferson didn’t just leave his mark on America’s government, but also on the nation’s appreciation of fine wine. Hit highlights of both Jefferson and 40 local vineyards on a driving tour.
Do: Visit Monticello, Jefferson’s plantation, which offers an honest look at the complicated life of America’s third president. Sample locally sourced food at Petit Pois, a charming French bistro downtown.
Stay: Boar’s Head Resort is a favorite with sporty families thanks to its indoor tennis facility, widely regarded as one of the best on the East Coast. At Keswick, the high-glamour vibe is enhanced by the sleek bar at Marigold by Jean Georges, which features a notably deep Euro-centric list of wines by the glass.
