There is plenty to see and do on the 70-mile peninsula that makes up the Eastern Shore of Virginia. From south to north the region’s charming towns and villages have a growing numbers of hotels, B&BS, shops, restaurants, art galleries and studios, and outfitters to take you exploring on land and water. Six public beaches range from deserted stretches accessed only by boat or a hike, to the drive-up convenience of Assateague Island near Chincoteague. Whether you approach from the north or the south, use this itinerary to help you dig deep into the region.
Chincoteague Island National Wildlife Refuge: Home to Chincoteague’s famous wild ponies, boasts a life-guarded beach, a non-lifeguarded beach that is a favorite for surfers, a beautifully restored lighthouse and a system of nature trails. This is a favorite spot for birders and nature lovers. With nearly 20 miles of white sand beach Assateague is perfect for long romantic walks or beach hikes.
Once you’ve worked up an appetite chose from dozens of locally-owned restaurants that serve up everything from fresh caught seafood to downhome cooking. Crab shacks, organic sandwich shops, seafood restaurants, raw bars, food trucks, bistros, cafes, diners, ethic food – there are lots of choices. There are some big hotel brands with adjoining restaurants too.
Historic Downtown: Stroll Chincoteague’s quaint downtown, which is lined with shops where you can buy everything from beach supplies, to boutique clothing, books and local art.
Island Creamery: No trip to Chincoteague is complete without a stop at the Island Creamery. Voted number one in America, this ice cream parlor home makes all of their ice cream in small batches.
Getting a taste of the salty, fresh oysters that Chincoteague is known for is a must while on the island. From raw bars to seafood shacks, oysters can be found on just about every menu in town.
You can wake up on the water, sleep under the stars or find your home away from home in a local hotel, campground, vacation rental or B&B. Expect local charm everywhere.
Cruise the Island: Hop on a boat and tour the island, watching for views of wild ponies and wildlife, or if you go at sunset, a gorgeous end to the day.
NASA Visitor Center: Learn about the past, present and future of NASA’s Wallops Island Flight Facility where the U.S. launched its first rocket in 1945. This visitor center also serves as a prime spot for viewing rocket launches from the flight facility.
Wright’s Seafood: Head out of Chincoteague and meander off-the-beaten-path for lunch at Wright’s on Wallops Island, where you can enjoy fresh local seafood with a spectacular waterside view.
Parksley: Head south to visit Jaxon’s Hardware, an old school five and dime store where you can find everything from souvenir T-shirts, to toys, penny candy and local gifts. After you’re done shopping stop in the Eastern Shore Railway Museum, which preserves the history of the role the railway played in the Eastern Shore’s past.
Onancock: This harbor town on the Chesapeake Bay has one of the Eastern Shore of Virginia’s best public harbors. Onancock’s main street is lined with boutiques, galleries and antique stores. Spend your afternoon hunting down the perfect souvenir to remember your trip by.
Onancock: There are nearly a dozen options for dinner in the village of Onancock, from pasta, burgers and sandwiches at Bizzotto’s Gallery and Café, to seafood and a waterside view at Mallard’s at the Wharf.
Rest your head at a boutique hotel or one of the town’s charming bed and breakfasts.
Janet’s Café in Onancock: Load up on a hearty breakfast at Janet’s. This kitschy eatery is a local favorite thanks to its generous portions and delicious dishes. The orange French toast is a best seller.
Ker Place: This late 18th century federal plantation home is filled with artifacts that recount the Shore’s long history.
Kayak Tour: SouthEast Expeditions’ guides will provide you with all the gear and guidance you’ll need to take a paddle around Onancock Creek.
The Island House: Head south to Wachapreague, one of the towns on the Eastern Shore where you feel closest to the sea. The Island House offers the best views of the wetlands and waterways that surround the town harbor with a distant view out to the Atlantic Ocean. They serve up delicious seafood, burgers and comfort food.
Boat to the Barrier Islands: Take an eco-tour out of Wachapreague to the only wild barrier islands remaining on the Eastern seaboard. After your marine adventures, take in an art stroll through Current Reflections Gallery.
Exmore Diner: Head over to the Exmore Diner, a local favorite. With the affordable prices and the sleek silver dining car design the Exmore Diner will make you feel like you’ve traveled back in time. With big portions of classics like fried chicken, seafood baskets and burgers you won’t walk away hungry.
You’re close by Exmore’s national hotel brands that line the main highway, Rt. 13. If you prefer, head off the beaten path and tuck yourself in at one of the gracious B&BS that are off the main road.
Machipongo Trading Company: This tiny coffee shop serves up breakfast sandwiches and locally- roasted coffee that will make a morning person out of anyone.
Barrier Islands Center: Right across the street from your breakfast spot, the Barrier Island Center preserves the history of those who once lived on Virginia’s barrier islands. This museum captures a lifestyle that is gone forever. The building that houses the museum once served as an almshouse. After taking in a history lesson stop by the museum’s gift shop, which is stocked with locally made artisan wares.
Wine Tasting at Chatham Vineyards: Just a few miles from the Barrier Island Center, Chatham Vineyards is a beautiful winery right on a Chesapeake Bay tributary. It’s producing award-winning wines which are capturing national and international attention. Take home a bottle of their popular Steel Chardonnay.
Yuk Yuk and Joe's: Head south a short distance to Yuk Yuk and Joe's, this roadside restaurant may look a bit like a dive, but locals always pack the house because they serve up some of the best pizza and wings on the Eastern Shore of Virginia. Their sweet potato biscuits are top notch as well. Give one of their perfect, crispy pizzas a try or swing by for one of their nightly drink specials and enjoy a plate of wings.
Eastville Courthouse Green and Buildings: Eastville’ s courthouse has the oldest continual court records in the country, dating back to 1632, and the Declaration of Independence was read on the Green in August of 1776.
Eyre Hall: This historic private residence has renowned public gardens, which are among the oldest in the country, dating back to the 1800s.
Savage Neck Natural Area Preserve: Reach a secluded beach after a hike through wild marine forest, and then take a dip in the Chesapeake Bay.
Oyster Farm Seafood Eatery at King’s Creek Marina (formerly Aqua) : Head south to Cape Charles and enjoy upscale dining in a modern setting with a breathtaking view of the Chesapeake Bay. The decks are a great spot to set up camp and enjoy a leisurely dinner hour or two. Ask for the red curry mussels; they were featured in Bon Appetit.
Brown Dog Ice Cream: End your night on a sweet note with a scoop of ice cream or an ice cream popsicle from Brown Dog Ice Cream. Flavors range from classics like chocolate to the exotic, such as Makers Mark and maple.
Lay your head down at one of the town’s bed and breakfasts, a vacation rental at nearby Bay Creek or King’s Creek Marina, or a boutique hotel.
Cape Charles Coffee House: Stop at the Cape Charles Coffee House for a great cup of coffee and a substantial breakfast. They’re known for their bagel and lox plate.
Explore Cape Charles’s historic downtown, which is dotted with boutiques, restaurants, galleries and specialty food stores.
Cape Charles Museum: Stop in at the Cape Charles Museum for a look back at the dramatic history of a town that was at the epicenter of the Eastern Shore railroad and ferry industries.
Cape Charles Beach: Finish your afternoon off with a walk on the town’s peaceful half-mile public beach.
The Shanty: This is a shabby chic seafood shack and the food is top notch and innovative. Diners can chow down on everything from local oysters on the half shell to Kogi beef tacos and a prosciutto and crab panini.
Tour Cherrystone Aqua Farms: Cherrystone is one of the largest producers of clams in the U.S. Tour their facilities and get an inside look at the ins and outs of the Eastern Shore’s aquaculture industry.
Eastern Shore of Virginia Wild Life Refuge: This park is considered one of the most important avian migration areas in the U.S., so of course the bird watching is top notch. In addition to wildlife observation, this park also features a WWII gun barrel from the U.S.S Missouri.
Sting-Ray’s: This is the perfect spot to grab some down home southern cooking and fresh seafood. If you’re lucky enough to visit during soft crab season try the crab imperial stuffed soft shell crab. If soft shells aren’t in season go for the crab imperial stuffed shrimp.