A weekend trip to Virginia’s Eastern Shore

After an unusually cool and wet spring summer’s warmer days meant one thing– it was time for a road trip. Steve’s Mom was in town and I wanted to show her a part of Virginia she hadn’t yet been to and a place that’s become a favorite of mine for a quick trip, Virginia’s Eastern Shore. Just an hour from my home in Virginia Beach this thin peninsula bordered by Maryland, the Chesapeake Bay and the Atlantic Ocean is only connected to the rest of Virginia by the 21 mile long Chesapeake Bay Bridge Tunnel and is easily reachable from both Washington DC and Philadelphia. Flip-flops and Wellies of the footwear of choice and oyster shell roads lead out to the water. The remote beaches, small towns and pristine barrier islands of the Eastern Shore feel both of another time and place making for the perfect Mid-Atlantic weekend getaway.

A Weekend Trip to Virginia's Eastern Shore www.casualtravelist.com

The first stop on our road trip was Cape Charles, an irresistibly charming town at the southern end of  the Eastern Shore.The effort of our early morning start was well rewarded with breakfast at the Cape Charles Coffeehouse. Locals and visitors are greeted with a wave and a smile at this charming two story cafe with the pressed tin ceiling. Our hunger sated by handcrafted cappuccinos and fluffy scratch-made pancakes we wandered through the shops, boutiques and art galleries along Cape Charles’ quaint Main Street. Cape Charles is also home to a bayside beach(and one of my favorite Virginia “LOVE” signs) whose quiet water and soft sand are a natural draw for families.

Cape Charles Beach-A Weekend Trip to Virginia's Eastern Shore www.casualtravelist.com

After our leisurely morning in Cape Charles we made our way up the shore towards the Garden & Sea Inn, a pet friendly pink gingerbread Victorian B&B near Chincoteague and our home for the night. After a restful night and tasty breakfast at our B&B we headed out for my first visit to Chincoteaague. Known most for the herds of wild ponies that call the barrier island home (including Marguerite Henry’s beloved Misty of Chincoteague, one of my all-time favorite childhood books) and the windswept dunes of the Assateague National Seashore, Chincoteague offers up a quintessential summer experience as it used to be. The barrier islands of Chincoteague are best viewed from the water so on an early Sunday morning we board the covered pontoon of Captain Dan’s Around the Island Tours. Long time island residents Dan and his father shared the history of the island while we viewed herds of wild ponies, the quiet marshlands of the barrier islands and the striped beacon of the Assateague Lighthouse.Turns out pony watching works up quite an appetite and luckily for us a host of new food trucks are putting out some of the best food on the island.  Farmer’s Daughter offers an updated take on classic comfort food ( the stuffed softshell crab and daily mac and cheese special are on point), while Pico Taqueria serves authentic street tacos with ingredients sourced from local farms. No visit to Chincoteague is complete without a stop by Island Creamery,  an Eastern Shore icon that’s frequently mentioned as making some of the best ice cream in the country.

The wild ponies of Chincoteague- A Weekend Trip to Virginia's Eastern Shore www.casualtravelist.com Updated comfort food at Farmer's Daughter- A Weekend Trip to Virginia's Eastern Shore www.casualtravelist.com

After our whirlwind tour of Chincoteague we hopped on Route 13 back towards Virginia Beach. For me no trip to the Eastern Shore is complete without a stop by Chatham Creek Vineyards where my friends John and Mills Wehner have been making wine since 1999. While I typically prefer to arrive by kayak on one of SouthEast Expeditions “Paddle Your Glass Off” kayak winery tours, today was just a quick stop for a tasting and a bottle of Church Creek Chardonnay to go.

Chatham Vineyards- A Weekend Trip to Virginia's Eastern Shore www.casualtravelist.com

While this trip to the Eastern Shore was quick I know I’ll be back sooner rather than later. Virginia’s Eastern Shore always has another secret just waiting for me to discover.


A Weekend Trip to Virginia's Eastern Shore www.casualtravelist.com

20 Comments on “A weekend trip to Virginia’s Eastern Shore

    • Virginia has so much to offer, you should definitely plan a trip!

  1. I definitely need to head out and explore more of the East Coast’s beaches. The winery also sounds like a great stop to add to your trip. Thanks for sharing.

  2. Brought out memories of our trip to the Outer Banks and Virginia Beach. I would have loved a photo with that LOVE sign just at the same angle you chose!

  3. Looks like an amazing weekend! I could feel the relaxed environment throughout your post and could imagine staying at the B&B and soaking up all that beauty. I have to say the winery sounded pretty good too :)!

  4. That part of Virginia looks so quaint and peaceful. Never been there, who knows, I might one day 🙂

  5. Wild horses and a pet friendly B&B, this seals the deal Virginia is officially on my list. I am always on the look out for places that can accommodate my pups 🙂 Your pictures are amazingly beautiful.

  6. This area looks so beautiful and restful – it’s nice to be reminded that the Virginia I know (you know, the part in DC area) is just a tiny bit of what this state has to offer. You know what sounds completely amazing – that kayak tour to the vineyard. Yes, please!!!

    • Heehee, one of my favorite parts about traveling in Virginia is finding all the different LOVE signs!

  7. Ahh I love those LOVE letters. It seems that so many places are getting them now, especially here in Holland, I love taking pics of them!

  8. That Eastern Shore looks pretty nice, Brianna! We’re going to explore our own Carolina coast first but will definitely have to hit some of these spots you’ve shared. Looks so lovely!

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