Like most avid travelers, I love exploring undiscovered gems and the 70-mile peninsula of the Eastern Shore of Virginia is surely one of them. This picturesque stretch has the Atlantic Ocean to one side and Chesapeake Bay on the other.

Settled in the 1600s, the Eastern Shore has preserved its old world charm and is filled with historical stories. But, there’s another side to the shore, a side that will have you suspended in the air on a hang glider or hiking through sand dunes to a secluded beach.

The Eastern Shore of Virginia is great for the history lover, but it’s also perfect for an outdoors fan like myself.

With two coasts, six beaches, charming coastal towns and the longest stretch of undeveloped barrier islands on the East Coast, there’s plenty of adventure to be had. And adventure is my middle name. I had the pleasure of trying every single one of these experiences while I was down there and you know what, these are things I would highly recommend. Whether you err to the dare devil side or are a romantic who just wants to enjoy some peace and quiet as you sojourn with nature, the Eastern Shore of Virginia has it all.

You just need to get off Route 13, the main highway that runs the length of the shore, and explore the best outdoorsy things to do in the nooks and crannies of the Eastern Shore of Virginia.


WHAT TO DO + SEE

The story about how the Chincoteague Ponies came to be on these islands (Chincoteague and Assateague) is mired in mystery. Which only adds to their intrigue. There are two main theories:

  • Theory 1: These ponies were let loose on the island by early 17th Century settlers in an effort to avoid taxes and building expensive fences around their livestock.
  • Theory 2: These ponies are shipwreck survivors who found themselves marooned on these islands during that rampant 16th – 17th Century period when there were a remarkable number of shipwrecks along the mid-Atlantic Coastline.

No matter which theory excites you the most, taking a day off to bike or hike into the Chincoteague National Wildlife Refuge to try and spot these ponies will definitely be something worth writing home about. You can easily rent a bike at the Bike Depot.

While you are in Chincoteague, take the time to enjoy all the other attractions that it has to offer. From eclectic art galleries to some of the best homemade ice cream you will ever have at Island Creamery (try a scoop of the appropriately named Pony Tracks), this funky beach town will keep you busy and absolutely elated all day.

P.S: If you go in July, you can watch the ponies take their annual swim from Assateague to Chincoteague Island.

Chincoteague Ponies on the Eastern Shore of Virginia
photo by John Williams

Have you ever had one of those dreams where you were a bird? Remember how free and liberated you felt? Well, on the Eastern Shore of Virginia, you will get a chance to have that experience in real life and check something amazing off your bucket list. At Virginia Hang Gliding there are a few things that they do differently: instead of jumping off a cliff, you will be towed up by a plane while strapped in tandem to a state-of-the-art glider with a professional hang gliding pilot.

Once you hit 2000 feet, 3200 feet, 4000 feet or a mile high (it all depends on how strongly your dare devil whispers into your ear), you will be set loose. From that moment on until you land, you will experience freedom like you have never known. Your pilot will go as crazy as you let him.

Tell him that you like roller coasters…I dare you!

You know how they say there are some places in the Galapagos Islands or the Antarctic that have never felt the footprint of man? Well, you do not have to go to such extremes to feel like the last person on this planet. By simply taking a ferry out of Onancock, you can sail to Tangier Island, home to one of the most pristine and isolated beaches this side of the United States.

About 12 miles off the mainland, a visit to Tangier Island is like escaping to a different world all-together. It is a world where the friendly locals are recognized for their distinct British dialect, cars don’t exist and the casual restaurants are known for the soft shell blue crabs (get you fill at Fisherman’s Corner!).

Tangier Island on the Eastern Shore of Virginia
Chesapeake Bay Program

The Savage Neck Dunes is something only the locals know about. And I am giving away the secret, because its beauty is meant to be experienced. An easy hike through a maritime forest leads to pristine sand dunes and a secluded beach (I was the only one there!). It’s completely FREE, so pack a picnic and a camera, and go.

This 300-acre preserve has to be one of the most secluded places in Virginia (outside of Tangier Island). On your hike, you will stumble upon miles of dunes, a mostly deserted beach and possibly some colorful butterflies or even a bald eagle.

Note: Spotting the parking lot on Savage Neck Drive is a little tricky due to limited signage and bad GPS directions. Look for the small gravel parking lot with a wide trail on the end. You can find directions here.

Annette White at the Savage Neck Dunes in the Eastern Shore of Virginia

On my way to Savage Neck Dunes (see #4), a wrong turn took me to an unexpected treasure. Don’t you just love when that happens? While heading west on Smith’s Beach Road in Eastville, I stumbled upon a tree tunnel so pretty that it deserved driving through multiple times.

A tree tunnel in the Eastern Shore of Virginia

For a chance to experience excitement and tranquility (I know, that’s contradictory) take a multi-day kayak trip with Burnham Guides. Design a tour that will take you through the local marsh salts, barrier islands and National wildlife refuge or Nature Conservancy. They also have packages that include hang gliding!

Burnham Guides specializes in these multi-day tours, and from firsthand experience I can see why you’d need more than just one day. After kayaking for a few hours through the beautiful marsh we were taken to Holly Bluff Guest House, where a catered dinner was waiting — fresh crab and oysters!

If you are more interested in just a day trip or to rent a paddle board talk to Dave at Southeast Expeditions.

Annette White kayaking the barrier islands of the Eastern Shore of Virginia

The salt marsh on the Eastern Shore of Virginia

Onancock is a quaint colonial town with cute shops and delicious restaurants, but it’s best to explore it from the water. At the harbor you can easily rent a paddle board from Southeast Expeditions and then launch just steps away. If you prefer, they can also take you on guided nature tours for the day.

From the launching point you can explore multiple creeks and even take a peek into the backyards of the historic waterfront homes.

Kayaking through Onancock in the Eastern Shore of Virginia

Do like the locals and spend the day relaxing on a sandbar. Along the delightfully picture perfect Chesapeake Shore lay a few charming sandbars that want nothing else but for you to enjoy with family and friends.

Some of these Sandbars appear with low tide while others are always there. To get to one, you can simply rent a skiff or a Kayak out in Wachapreague and ask the good people there where you can find the best sandbar. Hint: a popular one is Dawson’s Shoal, a few miles east of Wachapregue.

Information about skiff and kayak rentals can be found here.

A sandbar
Photo by Paul Gillard

WHAT + WHERE TO EAT

They say that to know the people, you need to delve into their local cuisine. Well, having a slice of Smith Island Cake is just one way to experience more of the Eastern Shore of Virginia. Though this cake is technically from Maryland’s Smith Island, the isle shares the Chesapeake Bay with the Eastern Shore, and that makes it a delicious tradition in both regions.

This delectable dessert is typically a whopping 8-10 layers of yellow cake and chocolate frosting. Though some shops are getting much more creative, making flavors like chocolate with peanut butter cream. Wash it down with a local cup of coffee from Eastern Shore Coastal Roasting.

You can pick one up at Becca’s Cakes or make your own using this recipe.

You will be the hit at any picnic if you show up with one of these cakes!

Smith Island Cake on the Eastern Shore of Virginia

What’s so special about having a crab cake on the Eastern Shore? It’s all about the freshness and no fillers attitude — the star is the crab! None of that 50-50 crab to bread crumb ratio.

You can find them just about anywhere in the region, but I did have a couple favorites. Both Mallards at the Wharf in Onancock and Island House in Wachapreague are award winning, and Annette approved! The “All Crab” Cakes at Mallards are made with nothin’ but crab and love. At Island House you can get them fried or broiled, I recommend the latter of the two. At both you have the option of sitting outside enjoying water views as you dine.

Island House crab cakes in Virginia

Crab Cake at Mallards on the Wharf in Onancock


WHERE TO STAY

Nothing says outdoorsy quite like sleeping in a peaceful cabin on an island that can only be reached by boat or kayak. The Holly Bluff Guest House is a charming 12-person cabin on the island of Holly Bluff that would be perfect for a family reunion, girls trip or group gathering. There’s no electricity, just propane tanks and solar, but that only adds to the tranquil experience on the Eastern Shore of Virginia.

If you book a kayak trip with Burnham Guides you will probably spend the night there, but you can also book on your own.

Holy Bluff Guest House on the Eastern Shore of Virginia

Annette White Holy Bluff Guest House on the Eastern Shore of Virginia

There are cute B&B’s scattered throughout the Eastern Shore, many of which have gorgeous wrap-around porches that are perfect for relaxing after all your outdoorsy adventures in Virginia. Here’s two of my favorites:

Sleep at the Inn at Onancock

The Inn at Onancock has it all. Charming Victorian front outdoors, and a new puppy dog (who may be all grown up by the time you get there). It’s a walking distance to the quaint downtown and to Mallards at the Wharf (remember? the place with the famous crab cakes?). The pillows and bed were so comfortable that I had to tear it apart to see why!

Sleep at Cape Charles House Bed & Breakfast

Have you ever been to a Bed & Breakfast that feel just like home, or better yet, Grandma’s place? Cape Charles House Bed & Breakfast is one of those B&Bs that go out of their way to make you feel right at home while treating you like royalty at the same time. Carol is a distinguished cook who has written for a national cooking magazine and Bruce has a wonderfully tended garden where the kitchen gets most of its herbs. That should give you an idea of the kind of meals and homely treatment you will get while staying at the Cape Charles House Bed & Breakfast.

For something more hip and trendy, check into Hotel Cape Charles. It doesn’t have a porch, but they do have rooms with balconies.

 Inn at Onancock B&B in Virginia

Cape Charles House Bed & Breakfast in Virginia

From pristine, secluded beaches to wild horses, fish forward cuisine and some of the most beautiful natural scenes you have ever borne witness to, the Eastern Shore of Virginia has it all. If you are going to go down there, plan to go for several days so you can take it all in. But if you don’t have that kind of time, then just pick one experience from these wonderful outdoorsy things to do and go for it.

Want more information about the Eastern Shore of Virginia? Go to Virginia is for Lovers.

Eastern Shore of Virginia Bucket List: Top 12 Things to Do

I was a guest of Eastern Shore of Virginia and Virginia is for Lovers. All opinions are my own.

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