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

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.

Eastern Shores of Virginia Bucket List: The Best Outdoorsy Things to Do

Eastern Shores of Virginia Bucket List: The Best Outdoorsy Things to Do

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.


1. See the Ponies of Chincoteague

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

2. Go Hang Gliding

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 — Hang Gliding! It is one of the top adventurous things to do before you die. 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!

3. Escape to Tangier Island

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

4. Hike the Savage Neck Dunes

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.

5. Drive Through the Tree Tunnel

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.

6. Do a Multi-Day Kayak Trip

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.

7. Paddle Board Through the Backyards of Onancock Creek

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.

8. Relax on a Sandbar

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


9. Picnic with a Slice of Smith Island Cake

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!

10. Snack on Crab Cakes on a Patio

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.


11. Sleep in a Cabin

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.

12. Kick Back the Porch of a B&B

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.

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.


Essential Tips for Visiting the Eastern Shore of Virginia

Getting There: The Norfolk International Airport is a major hub and most airlines will fly into it. You can easily check for the best fare deals at Skyscanner, which also has the option to choose ‘cheapest month’ as the departure to find the lowest priced dates to fly to your destination. From the airport to the Eastern Shore, pick up a rental car or take a taxi, Uber, or Lyft to your hotel.

Where to Stay on the Eastern Shore of Virginia: There are many options when it comes to accommodations on the Eastern Shore of Virginia. The Sunset Beach Resort (moderate) is a great choice located in Cape Charles. For something on the less expensive side, try the Shore Stay Suites in Cape Charles, or the Holiday Inn Express Hotel and Suites in Exmore. For a charming bed and breakfast with that extra cozy touch, book a room at the Fig Street Inn. Or search some great deals on hotels of your choice at Booking.com. If you’re looking for more of a home atmosphere (or are traveling with a group of people), head over to Airbnb that has houses, apartments and even just a room for rent in every price range. 

Getting Around: Renting a car in the Eastern Shore of Virginia is the best to really experience the peninsula, and RentalCars.com has some great deals. If you are not renting a car, taxis, Lyft and Uber are available all over the city.

Best Tours in the Eastern Shore of Virginia: You can find some of the top tours at Get Your Guide or Viator, and here are some of the top ones: South East Expedition Tours in Cape Charles 

  • Virginia Hang Gliding in Melfa 
  • Burnham Guides Paddling Adventures in Onancock 
  • This post may contain affiliate links. If you make a purchase through my links, I earn a commission that helps to keep this blog running—at no extra cost to you. For more information read my full disclosure.

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    12 thoughts on “Eastern Shore of Virginia Bucket List: 12 Outdoorsy Things to Do”

    1. Great, That is an awesome place and you shared great activities to experience beauty of Virginia. Its really awesome and stunning photos you shared of your trip.

    2. I heartily reccomend staying in Onancock during your adventure on the Eastern Shore. Its smack in the middle of the Shore, making it the perfect base to see the whole Shore. It is also the foodie capital of the Shore with many award winning restaurants.

      Evening entertainment may consist of live theater, music or an old time movie theater.

      There are numerous B&Bs in Onancock too. If you have children or dogs, check out the 1882 Colonial Manor Inn or the Spinning Wheel B&B. Luxury accomadations are at the Inn of Onancock. The Inn and Garden Cafe has its own restaurant and is across the street from Scoops, an icecream parlour.

      All of the travel lodgings are Green Certified for guilt free travel. Onancock was the first municipality to have all green lodgings.

      Not up for adventures like hang gliding? Onancock has several art galleries, museums and antique shops. Onancock was voted “the Coolest Town in the South” and the 11th Coolest Town in the USA by budget travel magazine.

      You can’t miss!

    3. This place is having blessings of God, every traveler finds it a worthy trip to visit there, Thanks for sharing this place.

    4. A romantic who just wants peace and quiet right here! Biking around Chincoteague National Wildlife Refuge to see those ponies sounds like a dream :)

    5. What an amazing post! Thanks for sharing your experience on the east coast! Gorgeous pictures and a great list of things to someday check out! Continue being an “Unstoppable Traveler and sharing your experiences with us!



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