Skip to content

Why You Need To Visit Virginia’s Eastern Shore

*A big thanks to Virginia Is For Lovers for sponsoring my trip. Great Eastern Shore getaways abound, and I was able to experience an incredible itinerary as part of their WANDERLOVE campaign*

Island hopping. Frozen pina coladas sipped while watching pastel sunsets. Kayaking out to sunken ships visible above the water.

No, I’m not talking about the Caribbean.

I’m talking about Virginia, specifically the state’s Eastern Shore.

This Virginia getaway is not your average seaside destination. Actually, its shore stretches for 70 miles, sitting between the Chesapeake Bay and Atlantic Ocean.

And you’ve got to cross the beautiful 17.5-mile Chesapeake Bay Bridge–Tunnel to get to it.

This bridge-and-tunnel structure was touted as “one of the seven engineering wonders of the modern world” by the American Society of Civil Engineers when it opened in 1964.

Unlike big city bridges that tower you above the water, driving over the Chesapeake Bay Bridge–Tunnel felt like I was gliding on water; so close I could almost touch it.

At sunset, this bridge is worth crossing just for fun. There’s a lookout point allowing you to stop and take photos near to the toll booth ($13) right before you reach your Eastern Shore getaway.

Chesapeake Bay Bridge–Tunnel
The Chesapeake Bay Bridge–Tunnel. Photo via Virginia Is For Lovers.

The best part?

Once you’ve crossed the bridge and emerged onto Virginia’s Eastern Shore, you’ll have stepped back in time. This is not only clear in the pace of life and the ability to visit historic mining towns and fishing villages, but also the way of life.

On Virginia’s Eastern Shore, there is a real focus on nature, conservation and working with what mother nature provides (vs taking it over).

In fact, most of the locals I met regularly caught their own seafood, and were passionate about projects that restored Virginia’s oyster beds and reduced plastic waste.

Want to experience this relaxing Virginia outdoors-focused destination for yourself?

Read my Virginia travel guide below to steal my unforgettable Eastern Shore itinerary!

Don’t forget to pin this post for later! 

There are many Virginia destinations to choose from when planning a trip, though if you love active vacations you won't want to miss Virginia's Eastern Shore. Here, you can go island hopping, hang gliding, seafood catching, beach hiking and more. Read on to learn what makes this Virginia travel gem so special. #Virginia #VirginiaIsForLovers #VirginiaTravel

Eastern Shore Destinations

Virginia’s Eastern Shore is made up of two counties — Accomack and Northampton — which each feature a number of cities and towns.

A few of the most popular Eastern Shore destinations include:

  • Cape Charles. This was the base for my Eastern Shore getaway. There is so much to do here, whether you want to hike in a state park, visit a local brewery or distillery, shop at local boutiques or have a fresh seafood meal on the water at sunset.
  • Chincoteague Island. Home to the namesake town of Chincoteague, as well as the wildlife-filled Chincoteague National Wildlife Refuge.
  • Wachapreague. From this small farmland-hugged town it’s possible to explore Virginia’s barrier islands and wetlands.
eastern shore getaways
From Wachapreague, I was able to take a boat trip to Virginia’s barrier islands
  • Onancock. Like with Cape Charles, you’ll find a number of natural attractions, a lively downtown district and a rich port town history. Additionally, Onancock is known for its gorgeous leafy green streets lined with Victorian homes.
  • Tangier Island. Only accessible by plane or boat, Tangier Island is a quiet, mostly car-free island, and is often touted as the “softshell crab capital of the world”. They say the island is sinking, giving another reason to add this to your Eastern Shore getaway itinerary in the near future.

Eastern Shore Virginia Map

While you browse potential Eastern Shore getaways, you can use this handy dandy map to get yourself acquainted with the geography:

eastern shore getaways
Eastern Shore Virginia Map via Virginia Is For Lovers.

A Great Cape Charles Hotel Option: The Northampton Hotel

As mentioned above, there are many destinations to consider when researching Eastern Shore getaways; though I do recommend Cape Charles, as there is a lot to do right there.

So, how would I describe this waterfront Cape Charles hotel?

Laid back luxury in the comfort of one’s waterfront dwelling.

Interestingly, Cape Charles was a booming port town during WWI and WWII when troops would pass through.

Moreover, visitors would need to take the ferry to Cape Charles to pass through to what was then mainland Virginia.

When the Chesapeake Bay Bridge opened, however, this was no longer needed. It wasn’t long before the hotel closed, left to decay.

That is, until May 2018, when it reopened as the opulent accommodation it is now.

eastern shore getaways northampton hotel
The exterior of the Northampton Hotel
eastern shore getaways northampton hotel
Just one of the many inviting spaces in the Northampton Hotel

As soon as I stepped into the historic property, the many spacious (and Instagrammable!) common spaces made my jaw drop.

Upstairs is where you’ll find the guestrooms, as well as a few other special amenities. Some highlights:

  • A 24/7 pantry room filled with free snacks and beverages — as well as usage of a complimentary Nespresso machine
  • A hallway shelf filled with board games
  • The “Widow’s Walk,” a winding staircase that’s over 100 years old leading to a tower lookout with 360-degree views (the perfect place in Cape Charles to greet the day with your free Nespresso!)
eastern shore getaways northampton hotel
I loved doing the Widow’s Walk and sitting up in this small lookout tower at sunrise.

In my room, the giant balcony with porch swing was my favorite place to start the day, while the uber comfortable bed and plush rooms offered the perfect way to end it.

eastern shore getaways
Enjoying a coffee on my porch swing at the Northampton Hotel in Cape Charles, Virginia.

Pro tip:

Don’t miss a stop in their gift shop, filled with local postcards, gifts and edible goodies.

Also, from the end of June 2018, the property will also be hosting a weekend brunch — complete with brunch cocktails — on their giant porch.

Getting Around Virginia’s Eastern Store

Even if you’re just staying in Cape Charles, you’ll want to rent a car to get to the parks and natural attractions.

Your best bet for finding a great deal on a car rental is to use a comparison site, like this one.

Actually, you can save up to 70% on your rental vs simply choosing a rental car company and booking without comparing.

Virginia Eastern Shore Getaways: Things To Do

If you’re an active traveler researching options for Eastern Shore getaways in Virginia, look no further. I’ve got your perfect itinerary right here.

1. Go Island Hopping (Wachapreague)

Hold up.

Did you know that Virginia is home to the largest stretch of uninhabited barrier islands on the eastern seaboard?

I didn’t.

In fact, I didn’t even know Virginia had islands to begin with.

My recommendation:

Begin your exploration of the islands at the Barrier Islands Center.

easrtern shore getaways barrier island center
The Barrier Island Center. Isn’t the exterior lovely?

Here, you can learn about the rich history of Virginia’s barrier islands. While they’re uninhabited today, a few of the them — especially Cobb Island and Hog Island — held hotels and were tourism hot spots.

Actually, many wealthy industrialists from the big cities up north would take the train down for their own Eastern Shore getaways, which ranged from hunting clubs to fishing trips to simply staying in immaculate hotels.

Unfortunately, the Depression combined with the powerful storms that followed led to locals literally picking up their houses and moving. In nearby Willis Wharf, you can actually visit Hog Island Lane, where these houses still sit.

At the Barrier Island Center, they’ve recreated many of the old hotel and hunting club spaces, using thousands of real and recreated artifacts.

eastern shore getaways barrier islands center
Historic recreations at the Barrier Islands Center

After visiting the center, take an island hopping trip around Virginia’s barrier islands with Captain Meriwether Payne of Seaside Ecotours (best contacted through her Facebook page or via email, [email protected]).

Virginia’s barrier islands are home to over 250 bird species, and Captain Meriwether Payne can tell you about all of them.

eastern shore getaways virginia's barrier islands
I saw so many birds when boating through Virginia’s barrier islands

On my trip, we spotted common terns, black skimmers, American bald eagles, and laughing gulls — a ton of them sitting on an island nesting and, not surprisingly, cackling with what sounded like laughter.

At one point, Captain Meriwether Payne let me out on Dawson Shoals — a large sandbar in Wachapreague Inlet — to explore the beach, my feet sinking into the soft sand.

eastern shore getaways
Exploring Virgnia’s barrier islands from the Eastern Shore

While there is almost no trace of the history that was here, there are a few remnants, like an old coastguard garage that’s now used by the Nature Conservancy for research, and a garden pavilion, now overgrown with sprawling vines, created by Mrs. Cobb for hotel guests on Cobb Island.

eastern shore getaways
This old coastguard garage is now used by the Nature Conservancy for research

You can let Captain Meriwether Payne know what you’d like to see, and she’ll create a custom itinerary for you.

After your tour, a great dining option is The Island House in Wachapreague.

Here, you’ll fill up on fresh seafood while taking in views of docked boats and scenic waterways.


This eatery is known for its soft-shell crab, a very popular seasonal dish in Virginia, and its crab cake sandwich.


Video by Chad Williams of Creative Visual Design for Virginia Is For Lover’s “WANDERLOVE” campaign

2. Explore The Many Eastern Shore Beaches (All Over)

The beaches of the barrier islands aren’t the only stretches of sand to lay out on.

Quite honestly, I felt like every time I turned around I saw another beach.

For instance, right across the street from the Northampton Hotel is Cape Charles Beach, where you won’t just find soft sand for beach-combing, but also a quiet fishing pier and, a bit farther down, volleyball nets.

If you like fun photo opportunities, you won’t want to miss the colorful “love” sign, too. In true coastal Virginia fashion, the sign is sea themed.

eastern shore getaways
The “love” sign and fishing pier at Cape Charles Beach.

Another great Virginia beach option:

The sister islands of Assateague and Chincoteague.

Within the over 14,000 acres of Chincoteague National Wildlife Refuge you’ll find wild landscape with lots of coastline to explore.

Moreover, it connects to the Assateague Island National Seashore, which stretches for 37 miles from Virginia to Maryland. The highlight of this beach is trying to spot wild ponies!

eastern shore getaways
Seeing wild ponies on the Assateague Island National Seashore. Photo via Virginia Is For Lovers.

3. Hike To Your Own Private Beach (Eastville)

Speaking of beaches, I’m adding another one to the list:

Savage Neck Dunes Natural Area Preserve.

There were a number of things that attracted me to this spot:

  • The name. I mean, who wouldn’t want to see up close how this park got such a title?
  • The promise of a unique mix of landscapes in a half-mile distance.
  • The fact that multiple locals told me it was their favorite park because “you can spend hours at the beach and see nobody.”

And so, I made the 25-minute drive from Cape Charles to Savage Neck Dunes Natural Area Preserve in Eastville, veering off from the highway onto quiet back roads as I got close.

I actually almost missed the small trailhead parking lot, backing the car up on the gravel road to turn in.

It didn’t look like much from there, but as soon as I stepped into the forest I was introduced to so many different elements in the span of 15 minutes:

  • The 4.6-acre freshwater Curtis Pond, an “interdune” pond home to frogs, turtles, fish and dragonflies
  • A green swamp that reminded me of something you’d see in Florida
  • A mix of forest ecosystems that ranged from coastal shrubs to maritime forest
  • Enormous sand dunes reaching heights of 50 feet that run for about one mile along the coast
eastern shore getaways Savage Neck Dunes Natural Area Preserve
The hike in Savage Neck began in a woodland setting
eastern shore getaways curtis pond in Savage Neck Dunes Natural Area Preserve
Curtis Pond within the Savage Neck Dunes Natural Area Preserve
eastern shore getaways Savage Neck Dunes Natural Area Preserve
Sand dunes with the Savage Neck Dunes Natural Area Preserve

The highlight, of course, is spilling out onto a white sand beach on the Chesapeake Bay.

And just like everyone promised, I had the beautiful Virginia beach all to myself.

eastern shore getaways Chesapeake Bay beach
I hiked through the Savage Neck Dunes Natural Area Preserve and had this beautiful Chesapeake Bay beach all to myself!

4. Kayak To A Private Island & Spend The Night (Cape Charles)

Have you ever had a travel experience that’s awesome, both because it’s unique and because you feel like you got to truly hang out with locals?

That is what a kayaking trip with Mary and Bill Burnham of Burnham Guides is like.

Video by Chad Williams of Creative Visual Design for Virginia Is For Lover’s “WANDERLOVE” campaign

Our group took off from the scenic Wise Point kayak launch within the Eastern Shore of Virginia National Wildlife Refuge in Cape Charles.

From there, we lowered ourselves into bright-colored sea kayaks, complete with back rudders for steering.

With the current, it took about 20-30 minutes to get to the day’s destination:

Holly Bluff, a private island with a 1920s fishing lodge that’s now an electricity-free guesthouse powered by propane.

eastern shore getaways
Welcome to Holly Bluff Island!

The decor features wooden decoy ducks and humorous fishing quotes, as well as photos and artifacts from its past.

eastern shore getaways holly bluff island
This is where you’ll sleep when spending the night on Holly Bluff Island

The Burnhams specialize in multi-day kayaking trips, and along with paddling to nearby Virginia barrier islands you’ll partake in beach picnics, al fresco yoga and chillin’ on the deck with wine under the stars.

eastern shore getaways
Holly Bluff Island is the epitome of serenity. Ommm….
eastern shore getaways
Exploring Holly Bluff Island

Another highlight:

Learning how to catch your own seafood!

I usually dislike raw oysters, but the ones here were briny and delicious — made even tastier after I hammered them off the oyster bed myself!

eastern shore getaways
Enjoying the sun on Holly Bluff Island

5. Learn To Fly — Literally — Through Hang Gliding (Melfa)

Now, not everything on my Eastern Shore getaway was water focused. Actually, you can have aerial adventures, as well.

I’ve gone skydiving, bungee jumping and paragliding; but never have a I tried hang gliding.

One reason:

There aren’t a ton of places that I’ve seen offer it.

Which is why when I discovered Virginia Hang Gliding was located in Melfa — just 35 minutes from Cape Charles — I knew I had to try it.

I’m not going to lie, I was pretty nervous beforehand; though, the owner of the company, Don “Freeman Coyote” Guynn, helped dissipate my anxiety.

Not only is he a USHPA certified Tandem Hang Gliding Instructor, but also a master comedian, at least in my opinion.

eastern shore getaways
Hang gliding on Virginia’s Eastern Shore. Photo via Chad Williams of Creative Visual Design.

Once we were strapped into the glider, a small plane took off from the field where Virginia Hang Gliding is located, and we effortlessly floated into the clouds.

It wasn’t too jerky or too fast, but peaceful and calm.

That is, until Donn decided to do some sharp sideways maneuvers that felt like I was zooming upside on a roller coaster.

A roller coaster that’s over 5,000 feet in the air!

eastern shore getaways
This is what it looks like to wang from the sky

Honestly, though, as soon as my stomach flipped, it was instantly (well, almost instantly) calmed by sights of the barrier islands, Chesapeake Bay, Tangier Island and the earth-colored plots below.

Out of all the aerial thrills I’ve had, this was by far the most serene.

6. Kayak Out To WWII Ghost Ships (Cape Charles)

Kiptopeke State Park is home to many outdoor Virginia activities, like hiking, fishing, beach-combing and camping, to name a few.

Probably the park’s most unique activity — and one I’ve never seen anywhere else — is kayaking out to nine ghost ships.

eastern shore getaways ghost ships
Aerial shot of the ghost ships by Chad Williams of Creative Visual Design.

These giant concrete vessels acted as cargo ships during WWII. After they were decommissioned, the ships were lined up and sunk to create a breakwater barrier.

Now, the sight itself is neat, and somewhat strange, to look at from the shore; however, kayaking up to the ships offered an entirely new experience.

Numerous bird species flew out of the vessels, and I even saw a giant osprey nest atop one.

Sometimes, the birds got so close I felt like I could touch them.

eastern shore getaways ghost ships
How wild is it that these sunken WWII ships are just sitting there for you to kayak up to?! Photo via Chad Williams of Creative Visual Design.
eastern shore getaways ghost ships
Look! There’s me, looking like a little Monopoly piece next to his giant WWII ship. A big thanks to Chad Williams of Creative Visual Design for taking this drone shot!

Something else incredible:

A large dolphin pod breeching out of the water!

As the boats are deteriorating you do need to keep a 50-foot distance; however, even from there I could see through large openings in the hull; a weathered glimpse into the boat’s former life.


Entrance to the park is $5/vehicle.

7. Hike Virginia’s Beach-Inspired Trails (Cape Charles)

Also in Kiptopeke State Park’s 562 acres:

5.1 miles of hiking trails, mostly flat and woodsy, and many leading to beautiful beach lookouts.

eastern shore getaways
A little trail yoga in Kiptopeke State Park

Many of the trails are short, but intersect with other paths, allowing you to hike for just a little, or longer if you prefer.

If you’d like to mix forest views with a secluded beach ending, opt for the Peregrine Boardwalk Trail. The short hike ends on a quiet sandy stretch that makes you feel like it’s all yours.

eastern shore getaways kiptopeke state park
Lush nature at every turn in Kiptopeke State Park
kiptopeke state park eastern shore getaways
This is where the Peregrine Boardwalk Trail ends up


While hiking, I stumbled across an incredible retro sign.

Apparently, there was a motel in this spot during the 50s, way before the park opened in the 90s!

eastern shore getaways
Incredible retro sign in the woods of Kiptopeke State Park on Virginia’s Eastern Shore

8. Shop Local In Cape Charles (Cape Charles)

I can definitely see why Coastal Living named Cape Charles one of the “Top 10 Happiest Seaside Towns.”

While “quaint” is an overused term, I’m using it here, because it’s just so darn accurate!

Locals and tourists ride golf carts down the street — often with their dogs riding shot gun.

You might also find them strolling the sidewalk full of “charming” stores.

Hey, these words just fit!

You don’t need a plan, and you can easily spend a few hours wandering the small locally-owned Cape Charles shops — no big chains here.

eastern shore getaways cape charles shopping
Wander Mason Street to find numerous local shops, many with a beachy twist

A few favorites:

Periwinkles. This women’s consignment shop offers chic clothing and accessories for really affordable prices, especially as you’ll find a number of name brands. New items arrive every single week, so there is always something new.

Love Letters. This breezy clothing store featured an explosion of pastel as soon as I walked in. Even if you don’t purchase anything, it’s a great stop for an instant happiness boost.

Like A Sailor. I was laughing out loud the entire time I was in this Spencer’s-esque local Cape Charles store. There are tons of inappropriate mugs, towels, t-shirts, books, games and more. As a cat lover, I think my favorite item was a coffee table book showing all the funny ways cats destroy our homes (but we love them anyway, because they’re so darn cute!).

eastern shore getaways cape charles shopping
A small glance at the fun items sold in Like A Sailor

The Cape Charles shopping options went well beyond just clothing stores.

In fact, there are a number of specialty stores, like Seagrass for floral home decor and terrariums, and Moonrise Jewelry where you’ll find lots of turquoise pieces.

Of course, in a town like Cape Charles you’ll have your quintessential beach shops; however, you won’t find cheesy cheap goods like in some areas.

Instead, local stores like Life on the Half Shell and The Boardwalk sell pretty wine glasses hand painted with fish, coastal scented candles and cards with sayings like “I love you to the beach and back.”

And finally, if you’re a fan of the arts, there are must-make stops like the Ellen Moore Gallery, the Lemontree Gallery and the Palace Theatre.

Pro Tip:

Along the way, make sure to cool down with a cone from Brown Dog Ice Cream.

eastern shore getaways cape charles ice cream
Brown Dog in Cape Charles makes homemade ice cream in very unique flavors

My flavor pick:

“Miss Josie’s Pretty Peas” laced with fresh local peas, mint, lemon, ricotta and avocado, topped with pistachios. I recommend getting it in a chocolate rim dipped cone!

9. Explore Cape Charles By Boat (Cape Charles)

Now, if you’re not feeling like paddling, or if you’d simply like a scenic sunset Cape Charles excursion, book a tour with Cape Charles Boat Tour Company.

While I explored Cape Charles thoroughly on foot, it was an entirely different experience exploring it from the water.

eastern shore getaways
Enjoying a sunset boat ride around Cape Charles Boat Tour Company

Not only did I see places I’d already frequented — like the Northampton Hotel and The Shanty Restaurant —from a new vantage point, but also brand new sites like pastel-colored homes along the Cape Charles Beach, osprey nests atop wooden posts in the sea, mounds of oyster shells along the coast to be planted in the seabed and, the highlight, the gorgeous sunset from the water.

This Cape Charles tour is a must-have Eastern Shore experience, especially if you’re traveling with your significant other. Next time I visit, I’m taking my boyfriend!

10. Savor Scrumptious Local Seafood (Cape Charles)

Now, when researching options for Eastern Shore getaways — specifically dining options — you’ll come across tons of delicious eateries, many boasting fresh seafood.

Though you can savor scrumptious seafood anywhere on the Eastern Shore, the Cape Charles restaurants I experienced were some of my favorites from the trip. This was especially true when I was craving a sunset meal paired with a tiki beverage (which, let’s be honest, was pretty much every second).

A few memorable meals at the Cape Charles restaurants I visited include:

The Jackspot at Sunset Beach. Dining here was actually my very first Eastern Shore experience, right after driving across the wildly scenic Chesapeake Bay Bridge–Tunnel.

The Jackspot is the type of place you could eat at for every meal of your Virginia vacation and not get sick of it.

Not only is the food delicious, but it’s one of the top waterfront Cape Charles restaurants, not to be missed at sunset.

eastern shore getaways
A delicious daiquiri at sunset at Jackspot

In between nibbling on blackened tuna bites and Chesapeake shrimp tacos, you can sip a strawberry daiquiri while bopping your head to Pitbull and steel drum music.

You might also head down to the beach and rent kayaks, or play a game of corn hole with a view.

eastern shore getaways
Pastel sunset at the beach in front of Jackspot in Cape Charles
eastern shore getaways
A delicious meal at Jackspot on Virginia’s Eastern Shore

On Saturday nights they feature live music, too!

The Shanty. This indoor-outdoor restaurant also delivered an epic sunset experience with my tasty tuna burger.

Sitting on the deck, pastel hues taking over the sky, was incredible; not to mention I got to try my first “Orange Crush,” invented in Virginia Beach

While I’d heard of this cocktail before, they’re not popular in New York the way they are in coastal Virginia. The libation features fresh-squeezed orange juice, vodka, triple sec and lemon-lime soda.

eastern shore getaways
Sipping at Orange Crush at The Shanty in Cape Charles
eastern shore getaways
Yummy tuna burger from The Shanty in Cape Charles
eastern shore getaways
Watching the sunset from The Shanty in Cape Charles

At The Shanty, they also offer creative twists on the drink, and you can get yours enhanced with grapefruit or cherry-lime.


The Shanty is walkable to The Northampton Hotel, so you can safely imbibe without needing a designated driver.

Hook-U-Up Gourmet (now Hook @ Harvey). Almost everyone I met on Virginia’s Eastern Shore told me that Hook-U-Up Gourmet was their absolute favorite eatery.

After dining at this Cape Charles restaurant for myself, I can see why.

Chef Timothy Brown is classically trained, and it shows in his dishes, which are mainly seafood focused.

While their menu changes weekly, some options when I went included pan seared jumbo scallops, fresh catch of mahi and a saffron-laced seafood fettuccine.

eastern shore getaways
Fresh catch of the day. Photo via Hook-U-Up Gourmet.

They also typically have a seafood-stuffed pastry as an appetizer on the menu.

While the offerings are dominated by seafood, you’ll find other options, too. The rack of lamb rubbed with honey Dijon was delicious the night I visited.

Despite the upscale menu, the ambiance is casual, like with almost all other venues in Cape Charles. And they serve local wine to pair!

11. Drink Up Locally (Machipongo + Cape Charles)

When researching Virginia’s Eastern Shore getaways, you may decide you want to add some imbibing to really relax.

The good news:

No matter what your libation of choice is, the Eastern Shore makes it locally.

First of all, there is a local wine region, which has been growing grapes since the late 1970s/early 1980s. The main grapes of the region include chardonnay, merlot, petit verdot, cabernet franc and cabernet sauvignon, with Chatham Vineyards in Machipongo being the place to try them.

eastern shore getaways
Chatham Vineyards. Photo via Virginia Is For Lovers.

If you like to mix your wine drinking with some activity, SouthEast Expeditions offers a kayaking wine-tasting trip that begins in the waterfront village of Bayford, down the Nassawadox Creek to Chatham Vineyards.

Not a wine drinker? No problem!

In Cape Charles, you’ll find the brand new Cape Charles Distillery crafting moonshine, whiskey and vodka. They also have a craft cocktail menu, and you can sip your drink on plush leather couches surrounded by boozy cocktail books and a chalkboard educating visitors on how liquor is made.

eastern shore getaways cape charles distillery
Sipping some apple pie moonshine at Cape Charles Distillery

Within a five minute walk is also the Cape Charles Brewing Co., which serves up two delicious IPAs, a pils and a stout, all inspired by the local Eastern Shore islands.

Finally, Buskey Cider on the Bay satiates the taste buds of those who love hard ciders.

12. Attend Popular Eastern Shore Virginia Events

If you’re Googling Eastern Shore getaways that align with a fun festival, this Virginia destination has many annual events.

Don’t miss:

Pony Polar Plunge (January). This annual New Year’s Day tradition is all about jumping into the icy Atlantic — in your craziest costume, of course. The event offers the perfect opportunity to be a part of something quirky and local you’ll never forget.

Low Country Shrimp Boil (April). Attention foodies: This tasty festival is hosted by the Cape Charles Museum every year on the last Saturday in April. If you love all-you-can-eat seafood with the fixins’, don’t miss it.

Chincoteague Island Oyster Festival (October). Coastal Virginia is known for its oyster heritage, which you can celebrate at this fun one-day festival where you’ll munch on raw oysters, steamed oysters, oyster fritters and more.

To help those planning their own Virginia Eastern Shore getaways, what experiences would you add to this list?

Enjoyed this post? Pin it for later!

About Jessie Festa

Jessie Festa is an New York-based travel content creator who is passionate about empowering her audience to experience new places and live a life of adventure. She is the founder of the solo female travel blog, Jessie on a Journey, and is editor-in-chief of Epicure & Culture, an online conscious tourism magazine. Along with writing, Jessie is a professional photographer and is the owner of NYC Photo Journeys, which offers New York photo tours, photo shoots, and wedding photography. Her work has appeared in publications like USA Today, CNN, Business Insider, Thrillist, and WestJet Magazine.

Jessie Festa standing in front of grafitti wall

Hi, I’m Jessie on a journey!

I'm a conscious solo traveler on a mission to take you beyond the guidebook to inspire you to live your best life through travel. Come join me!

Blogging Courses

Want to live your best life through travel?

Subscribe for FREE access to my library of fun blogging worksheets and learn how to get paid to travel more!



  1. Jessica on at 11:39 am

    I didn’t know much about this area before, but now I definitely want to visit!

  2. April on at 12:40 pm

    Clearly I didn’t take full advantage of living in Virginia (albeit I was in junior high at the time, but still). I didn’t even know about the eastern shore. Looks so idyllic with so much to do. thank you for all the great tips and ideas!

    • Nosilla on at 2:13 pm

      I love to sail and didn’t bring my own but found a sailing tour of Onancock. It was divine.

  3. Kathi on at 5:25 am

    Wow, I never even considered Virginia for a holiday before – but it looks amazing! The tunnel alone is such a novelty – would be great to experience that! Thanks for sharing!

  4. Caroline on at 5:24 pm

    I love how in depth this is… I’d admit that I never really thought of visiting Virginia (I haven’t been to many places around the US, to be honest!). But this has definitely gone on my radar now. Your photos are stunning too! I haven’t tried apple pie moonshine before, should be interesting and would love to check out the cidery!

  5. Sally on at 1:29 am

    What a great blog!! So glad to see my happy place so well documented…photos are amazing. I also stayed at the Northhampton Hotel…spent Memorial Day weekend on that same swing…the sunrise and sunset view is killer! The town has made an incredible comeback these last 15 or so years…happy to see the attention it is getting from blogs like yours!

  6. Elyn Mckenzie on at 12:31 pm

    Your trip looks amazing. You’re so lucky! I really like the look of the Northampton hotel. It’s just the kind of place in like staying in – lots of history and atmosphere. I didn’t know Virginia had islands, so thanks for mentioning that! We are off to Barbados this month, but you have inspired me to visit Virginia now.

  7. Wouter - Reisroutes on at 10:34 am

    He Jessy thanks for this unique piece of inside info … the abandoned ship is really amazing

  8. Chris Bloomfield on at 12:19 am

    Before we visited Virginia I wasn’t sure what to expect. You paint a picture that is spot on with our experiences. We have wild horses where we are from in Nevada, but it was still fun to see wild ponies strolling up the beach on Assateague. We didn’t get to hang glide though! How exciting and terrifying at the same time. The retro sign you saw looks neat. One of my favorite things is finding odd things like old signs or a crazy looking building. Of all the states we have visited, Virginia is the one I often think about going back to for some more fun.

  9. John on at 3:17 pm

    SOLD! Will definitely make a point to visit!

  10. Sam on at 12:49 pm

    Virginia looks like such a diverse and green place! Hadn’t really thought about going there before, but well… Now I certainly must visit this gem!!!

  11. Wow what an incredible post and amazing photos. Virginia was not really on my toplist for an USA roadtrip, but after reading this post it just made it on my wishlist. Thanks Jessie!

Leave a Comment