Annapolis, Maryland
Distance from DC: 32 miles; 1-hour drive
Why: Boats for DAYS, the gravitas of the Naval Academy, and a host of tasty treats
Three things to do while you’re there:
1. Cruise around the bay and take in all the sights Annapolis has to offer, including the Thomas Point Lighthouse. Take a water taxi to Eastport and down farm-to-table pizza at Vin909. If you are inclined to be a captain, spend the weekend learning how to sail.
2. Get nautical by using Air B&B to stay on a boat. Or, if you would rather sleep on dry land, try the Annapolis Waterfront Hotel, which takes full advantage of the beauty of the bay, while placing the attractions of the historic city within footstep.
3. Go on a bar crawl and hit up Dry85 for whiskey flights, Level for creative cocktails, BAROAK for beer, and Red Red Wine Bar for wine (duh).
Charlottesville, Virginia
Distance from DC: 117 miles; 2.5-hour drive
Why: This cozy town is part-historic and part-hospitality, because it serves as a launch point to check out some of Virginia’s best wineries. Its college-town status means top cheap eats and local activities.
Three things to do while you’re there:
1. Take on the Monticello Wine Trail featuring 20+ wineries. There are plenty of transportation companies ready to transport you safely from vineyard to vineyard. Early Mountain is a can’t-miss with its outdoor movies, live music, and dog friendly ‘tude.
2. Pony up for a one night’s stay at The Clifton Inn, and arrange to have dinner there. It lacks the creepy factor some B&Bs take on (innkeeper jokes about creaky headboards). If you are in the mood for a bigger splurge, check out a room at the Keswick, a breathtaking luxury golf resort & spa.
3. Stop at the Market at Bellair for the best sandwich you have ever had. Don’t let the location inside of a gas station fool you, the Ednam sandwich is truly transformative. To nurse your winery hangover, hit Ace Biscuit & Barbecue for breakfast, because there’s nothing like a fried chicken-, sausage gravy-, dill pickle- & smoked pimento cheese-topped biscuit for a slim $7.
Sperryville, Virginia
Distance from DC: 75 miles; 1.5-hour drive
Why: Prime access to Skyline Drive and Shenandoah National Park meets small-town charm
Three things to do while you’re there:
1. Stay the night at Hopkins Ordinary, a food-centric B&B that’s the perfect jump-off point for exploring. Dine al fresco across the street at the Thornton River Grille. The Inn at Little Washington’s a short drive away and if you have the cash flow, you should make it your thing. Eating there is a once-in-a-lifetime experience so it’s worth the astronomical price tag. The Inn thinks of everything. Personalized menus? Check. Toothbrushes in the restrooms? You’re welcome. A 1949 Rolls-Royce Silver Wraith parked out front, just in case a hotel guest wants to take a spin around the block? Vintage fun. When it comes to pulling out all the stops, few restaurants in the country can match the whimsy and excess of the dining destination conceived and nurtured by chef-owner Patrick O’Connell, all for the price of $208 per person.
2. Visit Copper Fox Distillery for a tour (offered every day). Learn how Rick Wasmund and his team make their single malt whiskey, rye, and gin. Then go home with a barrel kit.
3. Check “hike Old Rag” off your bucket list. It’s the kind of hike that involves using your hands and legs so leave Nana at home, but I have seen plenty of younger children doing it, and the view is worth the scramble. Bring a lunch to eat on the top for one of the most breath-taking vistas around.
St. Michael’s, Maryland
Distance from DC: 79 miles; 1.5-hour drive
Why: The entry point to Maryland’s Eastern Shore is full of personality and crabs
Three things to do while you’re there:
1. Channel Wedding Crashers and treat yourself to a pit stop at The Inn at Perry Cabin by Belmond where the movie was filmed. Have a snack at Purser’s Pub, like Blue Bay mussels in steamed in Dogfish Head 60min IPA, then stroll the grounds.
2. Visit local breweries and distilleries for tastings, including Lyon Distilling Company and Eastern Shore Brewing. Once ravenous, stop off for crabs at The Crab Claw or St. Michael’s Crab and Steak House.
3. Rent some kind of vessel from Shore Pedal & Paddle and get out on the water.
Chincoteague Island, Virginia
Distance from DC: 170 miles; 3.5 hour-drive
Why: The quieter side of the Eastern Shore is also the prettiest. And not just because of the ponies, although those are really something to see.
Three things to do while you’re there:
1. Your playlist should include The Stones because you’re about to see some Wild Horses at the Chincoteague National Wildlife Refuge. This is a highly Instagrammable moment, so trust Captain Dan.
2. Make a quick drive to try Smith Island Cake; it’ll ruin birthdays for you for the rest of your life.
3. Have a super-casual meal at Woody’s Beach BBQ. “The Pittsburgh” combines pulled pork, fries, slaw, and red sauce on a bun.
Bethany Beach, Delaware
Distance from DC: 121 miles; 2.5-hour drive
Why: Wide expanses of white sand and a nice boardwalk, close enough to lively nightlife and restaurants on the rise, but quieter than neighboring Rehoboth or Lewes.
Three things to do while you’re there:
1.Stay at one of the many rental properties along the beach or in the Sea Colony Condos, which offer a private beach with passes that come with your rental. The Dogfish Inn in Lewes. The local beer-themed inn was designed by Brooklyn hipsters, so expect some iconic Americana that will remind you of the movie The Endless Summer. If you want more Dogfish Head, visit the brewery in Milton.
2. If you’re going to do the whole boardwalk-nostalgia thing, do it in Rehoboth. Skee-ball, Grotto Pizza, and frozen custard don’t have to remind you of the Jersey Shore. But your best lunch bet is waiting for the Taco Reho truck to come around.
3. Park it at the Blue Coast for dinner, because the sea breeze has you craving briny bivalves and cold drinks. Or stop by Patsy’s for a Key West/Southern mashup that never fails to please.
Wisp Resort, Maryland
Distance from DC: 179 miles; 3-hour drive
Why: Tucked away in scenic Maryland mountains, Wisp offers an almost endless list of recreational activities for families, adventure seekers and nature lovers.
Three things to do while you’re there:
1. From whitewater rafting, kayaking, to the only mountaintop re-circulating whitewater course in the world, there are lots of ways to get wet in Wisp. There is also a mountain coaster and multiple golf courses in addition to all the hiking available around the mountain.
2. On the way, dine at D’Atries Restaurant for some of the very best cheese steaks, rivaling those from the north. On the mountain, try out Mountain State Brewing for pub-fare and beers, a nice reward for a day of outdoor activities with a very cool vibe.
3. Park it at one of the many rental houses around Deep Creek, because there is nothing like falling asleep tucked in among the mountains beside a shimmering moonlit lake.
