A Weekend Vacation Guide to Virginia’s Eastern Shore

Virginia’s gorgeous Eastern Shore is known for its oysters, outdoor activities, and pristine landscapes. Bordered by the Chesapeake Bay on the western side and the Atlantic Ocean to the east, the 70-mile peninsula is ideal for those travelers that embrace coastal living without the crowds.

TRIP PLANNING OVERVIEW

Get There: Be prepared to cross the Chesapeake Bay-Bridge Tunnel, a 17.6-mile roadway that spans the Bay. The toll can be paid with cash, credit card, or E-ZPass. 

Stay At: The Northampton Hotel for a historic stay with modern comforts in Cape Charles. Consider booking the Waterside Inn in Chincoteague, a family-owned hotel overlooking the bay. Plus, it's only a few blocks from the heart of the downtown area. 

Find more options for lodging on the Eastern Shore. 

Suggested Prior Reservations:

• Paddle Your Glass Off Tour with SouthEast Expeditions
• Onancock Sailing Adventures for a two-hour sail around the Eastern Shore
• Refuge Trek bus tour at Chincoteague National Wildlife Refuge

ITINERARY

Friday

Morning: Start your Eastern Shore getaway north of Cape Charles with the Paddle Your Glass Off Tour, a guided kayak tour to Chatham Vineyards led by SouthEast Expeditions. Embark from the banks of Nassawadox Creek, an inlet off the Chesapeake Bay, and paddle out towards Church Creek as your guide fills you in on the surrounding landscape. You’ll learn about the unique ecosystem and wildlife, the history of the waterway, and its current role in the livelihoods of local watermen.

After about a 45 minute paddle, your waterfront tour ends on the shores of Chatham Vineyards, where you’ll stroll across the shady estate grounds towards the tasting room. Built in 1818, the federal-style home of Chatham adds to the picturesque backdrop of the winery, and if you’re lucky, you’ll receive a very warm, and possibly slobbery, welcome to the property by Otis and Tucker, two friendly Labradors that call Chatham home.

Continue to the winery tasting room, where a knowledgeable staff will pour a flight of their current offerings. Even if you've been to countless wineries, you'll find the wines of Chatham distinct due to the soil found on the Eastern Shore. Oyster and clam shells have mixed into the soil over hundreds of years, creating an uncommon terroir that lends to the flavorful minerality of the wines.

Afternoon: Paddle back across the creek and hop into the car towards the downtown area of Cape Charles for lunch at Deadrise Italian Kitchen. Serving up wood-fired pizzas made to order, the restaurant sources locally whenever possible, making all doughs and sauces by hand each day. If you’ve brought your appetite, start with either the fried mozzarella or the house meatballs. 

Everything in downtown Cape Charles is fairly walkable, so leave the car parked and head towards the waterfront along Mason Avenue, which serves as the main stretch of shops in the town. Your first destination after lunch is Cape Charles Distillery, the first distillery on Virginia’s Eastern Shore. Sample their whiskeys, bourbon, moonshines, and vodka in a tasting flight or choose a few for a specialty cocktail flight, made using seasonal fruits, herbs, and other ingredients from local farms. 

Walk back to Mason Avenue and continue to Brown Dog Ice Cream for a refreshing sweet treat. With flavors like blueberry, banana cream, and malted milk balls, you’ll probably opt for more than one scoop. A helpful tip: Be sure to grab a handful of napkins before leaving Brown Dog, as they definitely don’t skimp on the scoop size and on hot summer days you’ll get some serious drips in a matter of minutes.

Evening: Wander back to the car for a short trip over to The Shanty for dinner. The local seafood spot is right on the water and has incredible views of the Chesapeake Bay. It also serves up some of the freshest oysters, crabs, and fish around. We recommend the crab cakes or the blackened fish tacos, paired with a cocktail from their extensive list. 

After dinner, head to the Northampton Hotel to check into your room before catching the waterfront sunset. 

Saturday

Morning: Have a leisurely breakfast at Cape Charles Coffee House. Housed in an early 20th century bank building, the restaurant has retained a lot of the historic charm, with much of the original woodwork throughout and an open second story dining area that overlooks the bistro below. If you’re feeling hungry, consider the French toast or Belgian waffles, both generous portioned plates with sides of fresh fruit.

Spend the next few hours browsing through a few of the shops in the downtown area, from cute clothing boutiques to shops that sell eclectic beach knick-knacks. A few favorites include Voiajer, a fair trade gift shop with colorful home décor and clothing ethically sourced from all over the world, and Moonrise Jewelry, a locally based jewelry company. They are known for their signature “fish leather” pieces, which have been cured, dyed, and gilded to create stunning one-of-a-kind earrings, bracelets, necklaces, and even handmade bowties and cuff links for men.

Before departing downtown, stop by Cape Charles’ beachfront LOVEwork at the end of Mason Avenue for a quick picture.

Afternoon: Located on the outskirts of the downtown area, Cape Charles Brewing Company has a beer list spanning a wide range of brews, from a double IPA to their award-winning porter, and you can sample the different styles in a flight tasting.

Cape Charles Brewing Company also offers a tasty food menu, sourcing most of the ingredients from local farmers, including seasona l produce and local seafood. Grab a bite to eat at the brewery before hitting the road for your next stop on the Eastern Shore: Onancock, a small but charming town about 45 minutes north of Cape Charles.

Travel down Market Street, lined with antique shops, art galleries, and small shops, to arrive at the Onancock Wharf Harbor. Set up a tour ahead of time with Onancock Sailing Adventures to get a customized tour of the waters. Owner and Captain Tom Bunino will share stories of the area, covering history, local legends, and the complex ecosystem of the Bay. 

Evening: Check in to Waterside Inn and get cleaned up before dinner. Chincoteague has a vibrant community of food trucks, including Woody’s Serious Food— a beach-themed shack serving pulled pork, baby back ribs, and other smoked meats with homemade sides and desserts. We favored the creative pulled pork sandwiches, such as the Big Hot Woody, topped with sliced jalapenos, Sriracha chili sauce, and their “Almost Famous” red sauce.

While the desserts at Woody’s looked appetizing, we saved room and traveled just down the street to Island Creamery, a Chincoteague staple that has been serving quality ice cream since 1975. Lines can get a bit long, but the staff at Island Creamery work quickly to get everyone’s order. Although the line was out the door when we arrived, we all had freshly baked waffle cones in hand within ten minutes.

Before ending the day at Waterside Inn, catch a memorable sunset from the Chincoteague LOVEwork, made from oversized Adirondack chairs that you can sit in for pictures.

Sunday

Morning: Start your Sunday with breakfast at Bill’s Seafood & Steaks in town. The upscale restaurant is well known for their impressive dinner menu, but they maintain the same level of quality in their breakfast fare. The menu mixes healthy options like homemade granola and egg white omelets with heartier dishes like corned beef hash and The Sportsman, a plate of three hotcakes with two eggs, home fries, and either bacon or sausage.

After breakfast, drive to the Chincoteague National Wildlife Refuge, a 14,000-acre reserve made up of pristine beaches, dunes, marshland, and maritime forests. The refuge provides a habitat for dozens of coastal wildlife species, like the Delmarva Fox Squirrel, the threatened Piping Plover, and of course, the famed wild Chincoteague ponies.

Reserve tickets ahead of your visit for a Refuge Trek, a bus tour of the wildlife refuge’s service roads. During the tour, you’ll see coastal wildlife in their habitats, and if you’re lucky, even catch sight of the ponies. If you prefer traveling on your own, there are numerous trails within the refuge that are open to the public, including a short trail to the Assateague Lighthouse.

Afternoon: Head to Pico Taqueria for lunch. Like Island Creamery, you’ll most likely arrive to a long line, but these tacos are worth the wait. They follow the motto “you can put anything on a taco,” specializing in recipes that blend local and international flavors. Add a homemade lemonade or limeade to your meal and grab a seat at the shaded tables behind the restaurant to enjoy a relaxing lunch before hitting the road for home.

More Trip Ideas: 

• Guide to Loudoun County
• Guide to Harrisonburg
• Guide to Richmond
• Guide to Nelson County
• Guide to Farmville
• Guide to Roanoke