Best Weekend Getaways from Washington, DC - The Eastern Shore, Middleburg, Washington, and Rehoboth
Curated By
Robert Huie
Curator’s statement
Whether it is winter, spring, summer, or fall, there is no bad time for a weekend getaway from Washington, DC. These are my four options for the best weekend getaways from Washington, DC. Eastern Shore, MD, Middleburg, VA, Washington, VA, and Rehoboth, DE are my go-to's. You can always use an escape from the city. Fortunately for you, there are plenty of options. Between an hour to three hours, via car, from Washington, DC, you can reach the ocean, the bay, or the country. These are easy drives. Three of which are family-friendly. Pack up the car and take a road trip; whether you are looking for a romantic getaway or a family getaway, there are plenty of options.
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Where to stay in Eastern Shore, Middleburg, Washington, and Rehoboth Beach
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Things to do in Eastern Shore, Middleburg, Washington, and Rehoboth Beach
The Eastern Shore (St. Michaels and Easton, MD)
St. Michaels, MD is a quaint town with great food, B&Bs and inns, and unique little shops situated on the Maryland Eastern Shore. As you drive down Talbot St, you will see the many storefronts of holiday decorations, clothing boutiques, bakeries, ice cream parlors, and many more. The food is amazing in St. Michaels, where you can get fresh seafood, particularly crabs and crab cakes. You can't mention St. Michaels without talking about the Inn at Perry Cabin. The Inn at Perry Cabin is a Victorian resort with a great pool, Pete Dye 18-hole golf course, tennis courts, full spa, and a waterfront view to die for. Grab drinks outside by the fire pit as you watch the sunset into the water. Make your way to STARS restaurant, where it showcases ingredients from the Eastern Shore. The Inn at Perry Cabin is a family-friendly location as well as pet-friendly.
If you are into fine dining, less than 20 minutes away, is the town of Easton, MD. In the center of Easton, head to the corner of Federal St and N Washington St. You will find Bas Rouge, The Stewart, Sunflower and Greens, and The Wardroom. Grab lunch at Sunflower, grab a bottle of fine liquor at The Wardroom. Before dinner, head to The Stewart, a bar and lounge serving fine whiskeys and vintage champagnes. Then head to dinner at Bas Rouge, with just 24 seats, a German and Austrian-influenced fine dining experience. Not something you would expect in this sleepy town.
Middelburg, VA
About an hour away is Middleburg, VA. Like St Michaels, it is a quaint little town. Once you enter the main street, you will just notice the charm of the 100 unique shops and restaurants. Not too far away from the center of town is the Salamander Middleburg Resort & Spa. Middleburg is a horse and wine country. Along your drive, you will encounter many wineries. At the Salamander there are plenty of activities ranging from equestrian, zip lining, hiking, falconry, golf, tennis, pools, river float wine tastings, cooking studio and more. I highly recommend the hike as it takes you through the entire resort, and you will see many historical landmarks along the way. Salamander Middleburg Resort & Spa is a family-friendly location.
If you do not fancy the restaurants at the resort, make your way into town. Check out King Street Oyster Bar for some seafood, fine dining at the Red Fox Inn & Tavern, or my favorite, The Restaurant at Goodstone Inn.
Washington, VA
There is only one reason to go to Washington, VA, The Inn at Little Washington. If you want a combination of a once-in-a-lifetime meal, romantic getaway, and retreat, head to The Inn at Little Washington. This is a luxury Bed and Breakfast. The restaurant portion of The Inn at Little Washington is a three-star Michelin restaurant, the only three-star restaurant within the greater Washington, DC area. An hour from DC, it is nestled in the Blue Ridge Mountains. As you enter the corner where the Inn is located, you will see what Patrick O Connell has transformed Washington, VA into. Take a stroll around the three blocks of the town to see the gardens created by the restaurant, different parts of the Inn, little quiet spaces to hang out, and the history of the buildings that surround the Inn.
Rehoboth Beach
About 2.5 hours away is the ocean. Specifically the Delaware beaches. Some of the most pristine beaches, along with great restaurants, entertainment, and shopping. If you visit in the off-season, it may be too cold to sit on the beach, but if you can catch it right as the summer season ends, after Labor Day, to avoid the crowds and enjoy the weather, as I have written in the previous article about The best time to visit Rehoboth Beach, Delaware. Rehoboth Beach is a family-friendly location.
Places to eat & drink in Eastern Shore, Middleburg, Washington, and Rehoboth Beach
Eastern Shore (St. Michaels and Easton, MD)
St Michaels, MD
STARS Restaurant - Located in the Inn at Perry Cabin - showcasing the ingredients of the MD. Eastern Shore.
The Crab Claw - Crabs and Crabcakes
Theo's - Steak
Carpenter Street Saloon - American Fare
Easton, MD
Bas Rouge - German and Austrian Fine Dining
Sunflower and Greens - Healthy salads, fresh food
The Stewart - Fine whiskeys and vintage champagne
Middleburg, VA
Red Fox Inn & Tavern - Fine Dining, Four-Course Dinner
King Street Oyster Bar - Oysters and seafood
The Restaurant at Goodstone Inn - French-forward, fine dining
Market Salamander - quick-grab, salads and sandwiches
Washington, VA
Inn at Little Washington - Fine dining, 3-Star Michelin Restaurant
Patty O's Cafe & Bakery - Upscale pub food
Rehoboth Beach, DE
See my guide on Rehoboth Beach, DE
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Looking for more travel inspiration? Check out my guide, The Best Time to Visit Rehoboth Beach, Delaware. This guide is part of our ongoing series on travel to Washington, DC.