48 Hours on the Eastern Shore

For those considering a trip to the Shore–and I hope you do!—I want to map out an ideal weekend full of local flavor.

Since everyone has their own unique idea of ideal, I’ll share with you many choose-your-own-adventure options, both on and off the beaten track, to fill your time. I grew up on the Eastern Shore and have lived and played here most of my life, so I’d like to explore from where my perspective is derived and why I’m absolutely smitten with this land between two waters…

image | Virginia Eastern SHOREKEEPER

I recently stumbled upon a letter I wrote to my future self, when I was in the 4^th Grade. “Hello Tatum, I hope you are having fun in sunny California, working at Disney Animation Studios, living on the beach, playing soccer with your dog and your best friend, Casey!”

As a young lady born in the late 80’s, growing up on the Eastern shore of Virginia, I am honestly not surprised why my future dream home would be located as far away as possible from this rural coastal peninsula. Growing up, there were only two movie theaters, each with only one showing two nights a week, and the ‘choice’ of only one movie. My parents had to drive 20 miles to get to the grocery store. I remember when the first kid my age moved to my town. That was when I was in the 3rd grade. There were no malls, no arcades, there was no shiny. Life was ‘Green Acres’ and I wanted ‘Sex in the City.’

Fast-forward to my college and post-college years, and I got my wish. And you know what, I loved it. But, no matter where I lived, from capital cities in other countries, to Richmond or Norfolk, Virginia, I always found myself escaping away to the paths less traveled: the river, the woods, the secret park behind the ball field. I found myself subconsciously trying to return to what I had thought I was trying to escape.

So I returned to the Eastern Shore. And I want to share with you some more reasons why…

As you cross over one of the seven manmade wonders of the world, the Chesapeake Bay Bridge Tunnel, and pass onto the first stretch of Shore, roll down your windows. If you are lucky it will be low tide and you can smell the richness of our wetlands. You’ll pass ghostly salt-blown tree groves topped by Eagle nests. You haven’t even traveled a mile north of the bridge, and there’s already some great things you can check out!

special thanks to the sponsor of this article Chatham Vineyards

Lower Shore

Things to Do: Just over the bridge, you have the option of visiting the first of two National Wildlife Refuges. This refuge is an important staging area for migratory birds and and is also used for the management and study of endangered species, such as the Northeastern Tiger Beetle and the Piping Plover.

A few miles north, Kiptopeake State Park is an amazing place to enjoy white sand beaches chocked full of awesome shells, hiking trails, camping grounds, and often times dolphin sightings. Cape Charles is the closest big-little town to you at this point. Rent a golf cart or set out on foot and enjoy amenities, including a free public beach, cute shops and galleries, as well as an Arnold Palmer/ Jack Nicklaus Signature Golf Course.

If you prefer to travel by boat, the Oyster Farm at Kings Creek boasts a state of the art marina, luxurious on-site villas, and the visitor’s favorite Seafood Eatery. If you prefer to travel by an even smaller boat, SouthEast Expeditions provides wonderful Kayak Tours from trained naturalists in two Cape Charles locations.

The next tiny town, of Eastville, boasts the longest continuous court records in the whole of the United States. I used to say this almost laughingly, but it’s actually a really interesting experience to stop off by the old court house and ask to view the records. You can peruse detailed quirky accounts of how Mr. Savage traded two chickens and a parcel of land to Mr. Pruitt in 1747; you can get a glimpse into the lives of the first settlers and Native American tribes, for which so many of our Shore towns are named.

Only 10 miles north of Cape Charles, you’ll find the two (maybe only one) horse town of Machipongo. There, Chatham Vineyards, a European style award-winning vineyard and working farm for over four centuries, which contains over 32,000 Chardonnay, Merlot, Cabernet Franc, Cabernet Sauvignon, and Petit Verdot vines, is open for daily tastings, and hosts fun events like their signature “Paddle your Glass off” Kayak tour.

Chatham is also in close proximity to the Barrier Island Center, which is a free museum and historical site completely dedicated to preserving Eastern shore culture and is a fabulous way to get a peek at unique regional artifacts and a greater insight to our rich watermen heritage.

Places to Stay: If camping at Kiptopeake State Park or Cherrystone Campground is not your style, Cape Charles offers a wide array of charming bed and breakfast options, or check out The Cape Charles Hotel for sleek accommodations (as well as an organic breakfast.) Close to the vineyard (and it’s always nice to be close to a vineyard) Green Valley Farm is a lovely B&B with an easy-going ambiance.

What to Eat: Cape Charles has many great restaurants, like the water-side Shanty, which sources the majority of their produce and seafood locally, as well as fun bars including Kelly’s Gingernut Pub.

Follow up your meal with the best local homemade ice cream of the county from Brown Dog. A little ‘up the road’ right on Rt. 13 is the Machipongo Trading Company. They have great sandwiches and locally roasted coffees from Coastal Roasting Co. Grab a snack and head around the corner to tour and picnic at the family-owned Chatham Vineyard, or enjoy one of Chatham’s cheese plates on the lovely historic grape-graced grounds.

Don’t forget to pack an iced up cooler so you can snag some delicious victuals from the Great Machipongo Clam Shack to bring back home. Frogs legs, she-crab soup, soft-shelled crabs, and other locally caught and sourced offerings of the Bay and Sea, are sure to be conversation starters back in your home-town.

Mid-Shore

Things to Do: Visit the quiet seaside fishing village of Wachapreague. Wachapreague is a prime place to rent a boat or charter to go out to the Barrier Islands. These pristine undeveloped grounds provide amazing shelling opportunities and you’ll traverse through miles of absolute picturesque and one-of-a-kind land and seascape.

Places to Stay: If you don’t head north for your next adventure, you can spend the night at the quaint Wachapreague Inn. They can also help arrange fun water-based activities. If you plan to stay here, be sure to ask if the annual Fireman’s Carnival is in town for the night!

What to Eat: The Exmore Diner is a frequent stop for both locals and visitors since 1954. This is a place where you can actually order a side of melted sharp cheddar, you know, for dipping. If you find yourself in Wachapreague, and want to grab a great meal with a fantastic on-the-water view, be sure to check out The Island House.

Upper Shore

Things to Do: About 10 miles north of Wachapreague is Onanacock, a bustling walkable town with lots to do and see. Get a glimpse of the Shore of yester-year by taking a tour of the free Historic Ker Place Museum. Also home of the Eastern Shore Historical Society, Ker Place has public gardens open year round.

Onancock is a bayside creek town and you have the option to rent a kayak or stand up paddleboard and set out on the creek solo or on a guided tour with SouthEast Expeditions. There are also a wide-array of cute galleries and unique shops, as well as some awesome antique deals to be scored.

If you happen to be in Onancock summer Saturday’s before noon, check out the Onancock Farmers’ Market, where you can buy local produce and eggs from happy pasture raised chickens from Shine & Rise Farm. Not-so-shameless plug: that’s my farm, but really all of the vendors are great; fresh-caught seafood, pick up your first piece of Mama Girl Papier Mache folk art, premium woolens from Ten Good Sheep, and other eclectic hand-made and home-grown goods.

Be sure to check out the summer Onancock ferry schedule in advance if you plan to enjoy a day-trip to the incredibly unique and legendary island village of Tangier, which is so isolated, that many of it’s natives possess the same accents of the original olde English colonists of the 1600’s.

About 45 minutes north of Onancock, passing the NASA Wallops Flight Facility (above), one of the oldest launch sites in the world (with free interactive educational center) you can visit the coastal community of Chincoteague. A family-friendly hot spot, Chincoteague was recently voted ‘America’s favorite beach community’ and has a fun flavor, boasting tons of family friendly activities. Chincoteague is the gateway to Assateague Island and the Chincoteague National Wildlife Refuge, where you can brush up on some hands-on environmental education, catch some great surf on one of our only public seaside beaches, take time to enjoy the many forest and coastal hiking trails, and get a glimpse of some remarkable wildlife, including the Island’s world-famous wild wetland ponies.

Places to Stay: Choose from one of the many charming bed and breakfasts of Onancock, such as The Inn at Onancock (below). If you end up staying or dining at the charming Charlotte Hotel, be sure to visit their bar and order one of their expertly crafted mixed drinks. My summertime favorite: the Fresh Mint Mojito! I can’t begin to explain how many lodging options there are in Chincoteague. Call around to see who has vacancies; the village is your oyster!

What to Eat: Enjoy some of the many delicious restaurants of Onancock – Including the Inn and Garden Café for brunch, Janet’s General Store for lunch, and Bizzotto’s for dinner. You can’t beat the creek-side view or singing (yes, singing) Chef at Mallards on the Wharf and you can wet your whistle at The Blarney Stone Pub.

If you’ve got the kids and just want a pizza, The Chesapeake Bay Pizza Co. has an awesome hand-tossed selection (my favorite is the Backpacker) and the newly renovated Fair Grounds, has a fun family-friendly arcade and great bar. If you decide to make the trip North to Chincoteague, you can enjoy a wide-array of lodging options, the best BBQ (at Woody’s), surf-n-turf at the homey Bill’s Seafood Restaurantn, write-home-to Mom sandwiches (including awesome vegetarian options) at the Sea Star Cafe, award winning- can’t miss ice cream parlors, and they even have a pony at their McDonalds. The sign next to the pony says not to feed him. I view this as an optional sign.

At this point, you’re only about 15 minutes south of the Maryland state border, so, assuming you actually still want to return to the life you came from, it’s about time to start heading back ‘down-the-road.’ Reflecting on your rustic escapades and wilderness adventures, the first hand experience of small town charm that most of us only get a glimpse of when hearing stories from our grandparent’s childhood, you truly understand the Shore’s catch phrase, because now you too, have Discover the Undiscovered…

About the sponsor of this article: Chatham Vineyards is owned and operated by the Wehner family on Virginia’s historic Eastern Shore between the Chesapeake Bay and the Atlantic Ocean. The land at Chatham, which overlooks Church Creek, was patented in 1640. Virginia’s Eastern Shore is an enchanting place of family farms, small towns and waterside villages. Watermen still work the tides and farmers plow the fields trailed by sea gulls. Fresh seafood, history, ecotourism and open space abound on “the Shore”. In addition, it is a registered American Viticultural Area (AVA) and is identified as such on our wine labels. We are proud to sponsor this story and hope you will taste the Shore with us soon. For more, click here for the website, here for their Facebook page, here for their Twitter, and here for their IG.

You may also like