An Adventurer’s Guide to 5 Days on Virginia’s Eastern Shore

Cape Charles in Virginia's Eastern Shore.
Cape Charles in Virginia's Eastern Shore. Malee Oot
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Dangling off the end of the Delmarva Peninsula like a slender tail, surrounded by the Chesapeake Bay on one side and the Atlantic Ocean on the other, Virginia’s Eastern Shore is a natural wonder. The water-fringed sliver of land is flanked by a string of barrier islands, and dotted with historic waterfront towns and pristine beaches, as well as more than 78,000 acres of preserved parks, refuges, natural areas, and conservation lands.

There are many culinary delights to be found as well in the region’s down-to-earth seafood shacks dishing up catch of the day, upscale bistros, raw bars, waterfront dining spots, and the dozens of culinary fests including a fall oyster roast every weekend. And, it’s all easily accessible; situated on America’s mid-Atlantic coast, the region is within half a day’s drive from 50% of the U.S population.

If you find yourself on the Eastern Shore celebrating the region’s gastronomic delights, be sure to stay a while; there’s much more to explore.

Day One

The quaint streets of downtown Chincoteague.
The quaint streets of downtown Chincoteague. Malee Oot

Begin along the ‘Upper Shore’ in the peninsula’s most famous location—Chincoteague. The historic island best known for its annual wild pony swim—which still happens every year in July—is the ideal place to explore by bike.  Starting in town, cycle to the Chincoteague National Wildlife Refuge along Maddox Boulevard, and explore the 14,000-acre protected area on two wheels. Begin with the 3.2 mile Wildlife Loop around Snow Goose Pool then pedal the refuge’s service road for just over a mile to the D-Dike Beach Access Area. Stash your bike and explore the Assateague Island National Seashore, a pristine 36-mile swath of wild beach stretching all the way to Maryland.

In the afternoon, switch from pedal to paddle—but first, detour to the Island Creamery for a brief refueling stop. Then, opt for a guided afternoon or sunset kayak tour of Assateague Island and the Chincoteague National Wildlife Refuge with Assateague Explorer Kayak Tours and Rentals, Snug Harbor Kayak Tours and Rentals, or SouthEast Expeditions. Or, rent a kayak or Stand-up Paddleboard (SUP) and set out solo.

Launch from the floating docks at East Side Landing or Fir Landing and hop on the Virginia Seaside Trail, a 100-mile paddling route that stretches the length of the Eastern Shore, from the Chincoteague National Wildlife Refuge to the Eastern Shore National Wildlife Refuge, at the peninsula's southernmost tip.

Day Two

Continue making your way south to the 'Middle Shore' town of Onancock, established in 1680. Head to SouthEast Expeditions and opt for one of three local paddling trips—a brief tour of Onancock Creek, a waterway explored by Captain John Smith over 400-years ago; a visit to an uninhabited barrier island for a private beachfront lunch; or the 'Paddle Your Glass Off' option, a trip to Chatham Vineyards along Church Creek, complete with a tasting tour and plenty of time to relax on the winery's picnic-worthy grounds.

Back on land, spend the afternoon wandering the pedestrian-friendly streets of Onancock, lined with Victorian-era mansions. Make your way to Ker Place, an 18th century Georgian manor turned museum, now the location of the Historical Society of the Eastern Shore. Once you've worked up an appetite, sample some locally sourced fare at the elegant Charlotte Hotel & Restaurant, the down-to-earth Janet's Onancock General Store and Cafe (serving breakfast and lunch), or Mallards at the Wharf, a waterfront establishment known for its musically inclined chef.

Onancock is also the jumping off point for visiting one of the most unique places in Virginia— historic Tangier Island, which was first settled in 1686.  If you have a day to spare, catch the Tangier-Onancock Ferry to unplug for the afternoon, wandering Tangier Islands car-free streets—and be sure to listen for traces of a Cornwall accent still coloring the local dialect.

Day Three

Stay in the 'Middle Shore' and make the short trip to the waterfront town of Wachapreague, on the Atlantic. Hop on your bike and ride the 12-miles from Wachapreague to Willis Wharf through the town of Quinby. In Willis Wharf, grab lunch at the Seaside Grill before returning to Wachapreague.

Ready to ditch the bike and hit the beach instead?  There are several options in Wachapreague. Head to the Wachapreague Inn to book a 3-hour clamming tour and spend the afternoon foraging for dinner (and working up an appetite) or hop the boat taxi to your own private sandbar and play castaway for the day. If you would rather explore Wachapreague on your own, pick up a kayak from Wachapreague Outfitters (757)787-2490 or paddle the waterfront town’s wildlife rich waterways on a history-laden guided eco-tour from Bay Country Kayak.  

If land and water still aren’t enough, explore the shore from above at Virginia Hang Gliding. Newbies to hang gliding can opt for a short introductory tandem flight for a bird’s-eye view of the area’s pristine beaches, lush wetlands, and shimmering waterways.  

Day Four

Keep winding southward towards the 'Lower Shore' and head for SouthEast Expeditions in the beachfront town of Cape Charles.  Explore one of the Eastern Shore’s most vital industries—and sample some of the region’s unique flavors—with a paddling trip to a local clam bed in Cherrystone Creek.  Learn about the recent revitalization of the Eastern Shore’s clam and oyster industry—which bounced back from the brink of an economic collapse in the 198os—and take your time sifting through the mud for some clams of your own to take home and prepare.

Or, savor the Eastern shore’s other cherished bivalve—the oyster—with a paddling trip to a local oyster rock.  For a one-of-a-kind oyster tasting and kayaking experience, Burnham Guides can arrange an overnight kayaking trip from Cape Charles to a restored 1930s-era hunting lodge on a private island—also offering the ideal opportunity to savor the unique flavor of one of the Eastern Shore’s three distinct oyster regions.  While on the island, track the tide and try your luck hunting oysters, clams, and crabs. Then spend the evening in the fully furnished Holly Bluff Island Guesthouse cooking up your catch.

In Cape Charles, SouthEast Expeditions can also arrange for another singular offshore overnight—a stay at Wise Cabin on a remote island. Spend a couple nights in the rustic, hundred-year-old waterman’s cabin—one of many that once dotted the Eastern Shore as oystermen steadfastly guarded their territory and their livelihood. A stay on the uninhabited island provides the chance to experience the solitude of an oysterman’s existence, as well as the opportunity to forage with the tide for your dinner fare.  

While on terra firma in Cape Charles, wander into the Cape Charles Coffee House for  a quick caffeine boost or indulge your sweet tooth at Brown Dog Ice Cream; you may even bump into Foster, the shop's affable canine namesake. Once you've refueled, amble over to the Cape Charles beach for a relaxing close to the day.

Day Five

Savage Neck Dunes Natural Area Preserve.
Savage Neck Dunes Natural Area Preserve. Malee Baker Oot

Begin at the Savage Neck Dunes Natural Area Preserve, about 3-miles outside of Cape Charles.  At the preserve, hike the blue-marked trail, winding first through a loblolly pine forest, then edging Custis Pond (be sure to look for Great Blue Heron), before the forest gives way to a mile-long ridge of towering sand dunes flanking the Chesapeake Bay -- including some of the highest elevations in the entire Eastern Shore.  Take a dip in the bay or wander the white-sand beach before retracing your steps to the preserve’s parking area.  

From Savage Neck, head south to Kiptopeke State Park -- steadily making your way to the Eastern Shore’s southernmost tip -- where the Atlantic Ocean and the Chesapeake Bay finally meet.  At Kiptopeke State Park, rent a kayak or SUP from the beachfront gift shop and take to the bay—and keep an eye out for local watermen working their lines. Back on land, meander the park’s 5.1-miles of trails—like the 1.5-mile Raptor Trail to Taylor Pond (and add on the 0.3-mile loop around the pond, if you still have energy to burn).

Once you've explored Kiptopeke State Park, hop on the Southern Tip Trail, a 2.5-mile multi-use trail paralleling the tracks of the historic Cape Charles Railroad, running from the Kiptopeke State park to the Eastern Shore National Wildlife Refuge. One of the most critical avian hotspots in North America—the protected refuge has recorded a staggering 406 different bird species.  

Eastern Shore National Wildlife Refuge.
    Malee Baker Oot
Eastern Shore National Wildlife Refuge. Malee Baker Oot

The refuge is also situated along a major migratory flyway—making spring and fall birding trips a must do for all birders. Take your time exploring the refuge. You can begin by hiking the half-mile Wildlife Loop, just be sure to bring your binoculars, and don’t forget to scan the skies for everything from songbirds to shorebirds to raptors.

Once you're done, it's time to head home with a head full of memories.

Originally written for Visit Eastern Shore VA.

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