Eight Big Outdoor Adventures on Virginia’s Eastern Shore

oVirginia’s Eastern Shore is an outdoor paradise. It is a sanctuary with six beaches, hundreds of miles of coastline, dozens of free boat ramps, thousands of acres of preserved land and hundreds of acres of bird habitat. For adventurers, surfing, sea kayaking, hang gliding and helicoptor and small plane touring bring thrills.

The best way to see the VA Eastern Shore. Credit: Burnham Guides

Coastal Kayaking
One of the best ways to experience and truly understand Virginia’s Eastern Shore is by kayak. You’re at eye level with nature exploring an undeveloped coastline that’s much the same as it has been for centuries. Explore miles and miles of creeks, islands and inlets on the Chesapeake Bay and the Atlantic Ocean.  Bring your own gear, or hire a local outfitter who knows the coastlines by heart and can design a custom trip for you. There’s lots to do by kayak here. Take an overnight camping trip to remote islands. Paddle to a wild oyster rock and slurp fresh caught oysters. Catch a glimpse of the wild ponies on Assateague Island. Head to the wild barrier islands out past the wetlands on the Atlantic. Paddle right up to a waterside vineyard for a wine tasting.  Watch a quiet and gorgeous sunset.


Deserted Beaches on Virginia's EAstern Shore - Copy
Experience the thrill of a deserted beach far out in the Atlantic Ocean.

Your Own Private Island
The longest string of undeveloped barrier islands remaining on America’s East Coast meander along Virginia’s Atlantic coast, creating a barrier between the 70-mile peninsula that makes up Virginia’s Eastern Shore and the Atlantic Ocean. Use your own boat or kayak, rent one when you get here or hire a local outfitter. When you walk in the wild sand of a deserted island, with no civilization visible for as far as the eye can see, you’ll feel just like the first Europeans landing in the New World. 


One of the world's top birding destinations. Credit: Virginia Tourism Corporation
The VA Eastern Shore is one of the world’s top birding destinations. Credit: Virginia Tourism Corporation

On Every Birder’s Bucket List
With hundreds of miles of wild coastline and thousands of acres of protected habitat, the Eastern Shore of Virginia is one of the most important bird flyways on the East Coast. Peak migration during spring and fall are excellent times to visit, but the winter season, when there is less foliage and cold temperatures transmit sound, are also ideal.  Take advantage of two wildlife refuges here, the Eastern Shore of Virginia National Wildlife Refuge near Cape Charles, and the Chincoteague National Wildlife Refuge near Chincoteague, or drive the Eastern Shore Birding and Wildlife Trail. More preserves and natural areas take you into hundreds of acres of wild habitats along both coastlines.


assateague - Copy
Surf’s up at Assateague Island National Seashore. Credit: Levi Smith

Surf’s Up
Whether you’re a surfer, a kite surfer, a boogie boarder, a skimboarder or a paddleboarder, the waters around the Eastern Shore are sure to quickly become a favorite spot. The Assateague National Seashore’s pounding waves offer a thrill ride for a variety of experience levels. The waters of the Chesapeake Bay provide a calmer experience, perfect for kite surfing, paddleboarding, skimboarding and boogieboarding at a slower pace.


A Chincoteague pony with her young foal grazes on Assateague Island.

The Wild Chincoteague Ponies
Thousands of people flock to Virginia’s Eastern Shore to watch the wild Chincoteague ponies take their annual swim from Assateague to Chincoteague Island in July. But any time of the year, you can spot them from a boat or kayak tour with locals who know where to find their secret hiding spots. If you are a horse lover who wants to see some of the local countryside from horseback, area stables rent horses and lead trail rides through the beautiful trails of Virginia’s Eastern Shore.


What a view. Credit: Virginia Hang Gliding

A Mile High View

Local pilots know all the special spots along the region’s Chesapeake Bay and Atlantic Ocean coastlines. Hang glide, helicopter or fly high above the two coastlines and see Virginia’s beautiful coastal vistas and wild barrier islands from an entirely new perspective. The silence and vast beauty will transform the way you see the world. You don’t have to have any experience to hang glide – certified instructors will teach you all you need to know.


The great fishing here is a well-known secret.
Over 40 free piers to fish or crab from. Photo: Sean Stauffer

Catch Your Dinner
Head out to the Atlantic Ocean with a local boat captain. They know where all the best spots are to land a big one and they have some great stories to tell. Fish for mahi-mahi, yellowfin, bluefin, wahoo, big eye and flounder. Or bring your own boat and use one of the 40+ free boat ramps along both coasts. If smaller game is your aim, cast a line off of one of the piers or docks around the Eastern Shore. Staff at one of the local tackle shops can tell you all you need to know about fishing the area’s waters. A lucky angler can land everything from flounder to croaker, drum, cobia, sharks, spadefish and triggerfish. Crabbing is also a popular pastime and any local hardware store will hook you up with all the supplies you need to land your dinner.


Bike the back roads.
Bike the back roads and discover tiny hamlets and ancient fishing villages.

Flat Terrain for Bicycling
The flat terrain of Virginia’s Eastern Shore makes it an easy place to explore on two wheels. Bring your own bike or rent one when you get here. On the southern end of the Eastern Shore, a paved 2.5-mile trail meanders alongside the Old Cape Charles Railroad bed through forest and farmland. On the northern end, about half of the Chincoteague National Wildlife Refuge’s 14 miles of trails are paved. Check out the calendar for annual bike tours – the fall Between the Waters Bike Tour and the spring Le Tour de Shore — have well-marked routes that take you to places you might never find on your own.

To plan your visit to Virginia’s Eastern Shore click here.

You may also like: An Adventurer’s Guide to 5 Days on Virginia’s Eastern Shore
The Route Less Traveled: Boating the Chesapeake Bay’s Eastern Shore
Explore Virginia’s Eastern Shore by Bicycle

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