Cape Charles, Virginia: A Guide To The Beach Town

I know it is odd to be posting a beach-centric travel guide after summer’s over, but Sherry has been fielding so many questions lately about what to do in Cape Charles that we hoped all the answers in one place. Now people can simply drop in on this post for all the details. And boy, are there details (have you met me? If not, hi, I am John “Thorough” Petersik).

The first question is consistently for the link to our Airbnb (the Doublemint Duplex) so here is a link to the left side & here is a link to the right side.

And no matter where you stay, if you are thinking of making a visit to our go-to little beach town (which was also lately voted #3 Happiest Seaside Town by Coastal Living!), or are simply curious about why we chose this place to renovate two vacation homes, this post is for you! We are covering some lively activities for the family, our go-to meal places, and other reasons we think Cape Charles is the ideal place to unwind and soak up some fairly memorable sunsets.

Where Is Cape Charles?

Cape Charles is located near the southern pointer of Virginia’s Eastern Shore right on the Chesapeake Bay. The Eastern Shore is a small, rural portion of the state that is separated from mainland Virginia by the Chesapeake Bay. Cape Charles is a small town (the historic area is roughly a six block by six block square) that sits on the peninsula’s western coast… meaning you can sit on the beach in Cape Charles and watch the sunset right over the water. Highly recommend that.

It is about a 2.5-hour drive from our home in Richmond, which culminates in crossing the Chesapeake Bay Bridge-Tunnel, a 23-mile long stretch of several bridges and two tunnels that offers quite the impressive welcome to the area (vivid water views). It is also accessible from the north via a quiet drive through Maryland (it is about 4 hours from Washington DC). Or, if you need to fly, the Norfolk International Airport is simply across the bridge-tunnel – about 45 minutes away.

The town is relatively unknown and only in the last 5-10 years has it been experiencing an upswing as people have discovered it as a low-key alternative to your typical beach town, which means plenty of homes are getting fixed up, new restaurants and shops are opening up, etc.

It has been truly remarkable to watch this town spring back to life and be revitalized, beautified, and enjoyed. Especially because the historic area is home to hundreds of striking 100+ year old houses, many of which needed a lot of enjoy, and many of which have been lovingly restored. And our two are tucked right into the middle of it all.

The Beach

First lets talk about the beach, because it is what sold us on Cape Charles (and it is typically our go-to place every time we visit). It is uncrowded, low-key, and straightforward to get to. Since it is on the Chesapeake Bay, not the Atlantic Ocean, the water is calm and shallow.

At high tide you can walk out several dozen yards and still be barely waist deep in most parts (I am sitting in the photo below, so the water is only about 18″ deep there) and at low-tide you can park your beach chair right in the water to keep your feet cool. It attracts plenty of families like ours because kids can play for hours in the water without us parents having to fear the break of a big wave or the pull of a sudden riptide.

Our kids have spent HOURS splashing around, riding on floats, or even hunting for hermit crabs (yup, you can find them walking around on the sand in low tide).

Yup, these are all little hermit crabs we collected one evening at low tide. They are such a novel thing to discover with kids, and they can put them in a bucket to watch them swim (and even witness them switching shells if you are lucky!) and then toss them back in the water before heading out.

I you crave a bit more activity when you go to the beach, Cape Charles Beach is strong for kayaking, stand up paddle boarding, fishing, jet skiing, or boating. On a windy day you will even see kite boarders. If you do not have your own, there are a couple of rental places, like SouthEast Expeditions and the Oyster Farm at Kings Creek.

The other strong thing is that PARKING IS FREE AND PLENTIFUL! You can park right along the beachfront street, Bay Avenue, with no problem – even on most summer weekends. No circling the block to find a spot or having to pay for metered parking. We ENJOY that fact. There are also public restrooms with showers behind them near the big “ENJOY” sign at the corner of Mason Ave & Bay Ave, and on summer weekends there is frequently a delicious taco truck and an Italian Ice stand parked nearby.

Where To Stay

For such a compact town, there is a surprising variety of options for your stay. We should first mention that there are vacation rentals through sites like HomeAway and Airbnb, which can be strong for long stays, like a full week. The one shown below was even featured on HGTV! Simply be mindful that those sites frequently return results outside of the historic district (but being inside the historic district is where you will get the most proximity to the beach, shops, and restaurants). So simply double check that it is in fact in Historic Cape Charles if you plan to walk to shops, the park, the beach, restaurants, etc.

There are also a lot of bed & breakfasts in Cape Charles, like the Bay Haven Inn (below), Cape Charles House, and Alyssa House to name a few. We had the chance to visit several during a holiday open house event and they are all striking with strong historic details.

Another strong option, especially for shorter stays, are hotels. The two in town are both Excellent, but quite distinct. Hotel Cape Charles is a modern “zen-like” hotel with loft style rooms (think: exposed brick, reclaimed wood, and those glass balconies that you see in the photo below). They also have lively perks like golf carts and bikes that are available to guests. We stayed there one night while tiling the pink house and enjoyed it!

By contrast, the newly opened/restored Northampton Hotel has water views (it is closer to the beach) and a more historic/Southern feel (like a giant front porch with a blue ceiling where you can have coffee and breakfast, with plenty of traditional and ornate details like wallpaper, detailed molding, etc). There are also some more bargain-priced hotels and motels simply outside of Cape Charles if you simply need a place to plop your head at night.

Lastly, Kiptopeke State Park offers campsites and a few cabins (even a yurt!) nearby – as does Cherrystone Campground. Both are also waterfront, so you can enjoy the beach there without coming into town. But we’d certainly recommend venturing into Historic Cape Charles simply to check out a few of the places we are about to talk about below.

Where To Eat

The restaurant scene in Cape Charles is, well, not quite a scene yet. But that does not meant there are not plenty of good meals to stuff in your face hole. Most of the commercial action in Cape Charles is concentrated on Mason Avenue, the town’s de facto “main street.” But our go-to dining spot is in fact a short distance away, called Shanty. It is a casual seafood place, complete with an oyster shell parking lot and an old boat out front full of plants. It has a ton of fresh fish tuna, shrimp, and oysters (for either lunch or dinner) as well as strong options for non-seafood lovers and children as well (chicken fingers, quesadillas, burgers, etc).

It is on the water so you can catch strong sunsets, and in the summertime they frequently have live music on weekends. It is popular with locals and visitors, so if you want to avoid a long wait it helps to come early (before 5:30 is the best time to aim for), or get a reservation (typically you have to call the day before to score one). Or simply put your name on the list and they’ll text your phone when your table is ready – so you can walk around outside or even play corn hole out back and watch the boats in the marina while you wait.

Another go-to of ours is Deadrise Pies, which is a pizza/Italian place operated by the Shanty folks.

It is also especially kid-friendly, has strong outdoor seating, and is also truly pleasant when you need some straightforward carryout. We frequently get pizza and take it to eat on the beach at sunset! Some argue that Gerry’s Ristorante outside of town has better pizza (we like ’em both) but Deadrise wins for location and ambiance.

A newer go-to of ours is Cape Charles Brewing Company, which serves food and has strong outdoor seating. We ate at shaded picnic tables while the kids played corn hole and ladder golf nearby and it was ideal!

Kelly’s Gingernut Pub is also a good option for kids, and people recommend Hook-U Up and The Oyster Farm for nicer adult date-night dining excursions, but since we have consistently got kids with us we have not tried them yet.

Our go-to spots for breakfast are the Cape Charles Coffee House and the cafe at The Northampton Hotel (above), or you can eat more casually at Rayfield’s soda fountain. We like to grab lunches at Gourmet Alley or Tim’s Place too. There are also other staples outside of town (like fast food and carryout Chinese) and in other exciting news: it looks like we are getting a couple of new bakeries soon!

Where To Treat Yourself

A satisfying meal is all well and good, but one of our go-to parts about Cape Charles (and, well, life in general) is DESSERT. And if you are more into the “grown-up desserts” (aka, drinks) we will cover that here too.

Reigning dessert champ in Cape Charles is Brown Dog Ice Cream. This charming ice cream parlor with an ever-rotating menu of flavors was named among the “Top 10 Best Ice Creams in America” by TripAdvisor. They’ve got plenty of classic flavors, but I consistently enjoy their experimental ones with names like Lemon Curd Coconut Hot Milk Cake and Peach Raspberry Goat Cheese Crumble (the one below with sprinkles is Caramelized Fig with Mascarpone & Coco-Ginger Dust). And you can get any flavor as a milkshake, malt, float, or an ice cream sandwich too.

The new kid in town is Peach Beach Shave Ice Shack, which was began out of someone’s shed. They shipped in an authentic Hawaiian shave ice machine to make finely shaved treats that are distinctly better than your typical snow cone. Plus, the interior is especially charming! They are only open in the summer season for the most part, but they are excellent on a hot day.

A less known, but also less pricey dessert option is CC Kool Eatz, which is hidden in a residential area on the north side of the historic downtown district (at the corner of Jefferson & Strawberry). They have some strong soft serve with little tables to enjoy it outside. We also got a new candy shop this year, the Cape Charles Candy Co, which was opened by the family who was featured in the episode of HGTV’s Beachfront Bargain hunt that our house photobombed!

As for places to grab an adult beverage, in 2018 Cape Charles got a brewery, a distillery, and a cidery. Sherry likes to call it the trifecta of hipster spots to grab a drink – and they each have some fairly strong atmosphere and that craft-brew feeling. As I mentioned above in the food section, the Cape Charles Brewing Company serves meals for the whole family and has plenty of outdoor space as well as craft beer (flights, samplers, etc). We have not been to Buskey Cider on the Bay yet (an offshoot of a Richmond cidery!) but it has plenty of board games and outdoor games (think oversized Jenga) on their outdoor patio. The Cape Charles Distillery is a decidedly more grown up space that sells upscale whiskeys, bourbons, moonshine, and vodka.

And if wine is your thing, Chatham Vineyards is simply up the road. They even offer a “Paddle Your Glass Off” tour where you kayak to the winery on a guided tour and then get to sample some wines when you get there.

What ELSE To Do

You’ve hit the beach, stuffed your belly, and enjoyed the sunset. Now what? Cape Charles is certainly a quieter beach town than those you may think of with a boardwalk, mini golf, arcades, and outlet malls (although there is one of those beaches right across the bridge). So our “to do” list here typically involves a lot of relaxing, walking, and exploring.

The town’s main street, Mason Avenue, has plenty of charming shops – including beach souvenirs, decor, clothing, jewelry, vintage furniture, art, wine, and more. Some of our go-tos for browsing are Chuckletown Productions, The Boardwalk, Destination 23310, and the gift shop at The Northampton Hotel (seen below).

There is also a large park that is centrally located in the historic district (yup, it is in fact called Central Park – simply like our old go-to in NYC). It has a large public field for tossing or kicking a ball around, a walking path, a playground, and tennis courts. We use it most for the playground and every Saturday in the summer they host live music in the gazebo and people bring lawn chairs and food/drinks to enjoy on the field while they watch the musicians play.

We typically end up doing a lot of walking around the downtown area to check out all of the houses (especially if we remember to bring the kids’ scooters). But if you want a more natural hiking spot, the Cape Charles Natural Area Preserve is a shaded boardwalk through the woods that is simply a short drive from town (I run there in the mornings from our beach house). Further out of town is the Southern Pointer Hike & Bike Trail which is a wide 5-mile paved trail that terminates into a Nature Center that we have not visited yet, but we hear it is good for kids (it and Kiptopeke State Park have more trails too).

We also truly enjoyed a visit to the Barrier Island Center about 15 minutes up the road…

…and we took a day trip about an hour north to Chincoteague Island this summer to see the wild ponies. That was INCREDIBLE. We took this tour, but we hear there are a bunch that are good.

Cape Charles is also strong for fishing, crabbing, boating, and golfing – but none of those are pastimes of ours so we are not truly qualified to advise on them. But there is a free fishing pier in town and simply outside the historic district are two signature golf courses (one Nicklaus, one Palmer – that means something right???).

When To Visit

Someone asked lately if there is anything to do in Cape Charles in the off-season. The answer is “Yes!” but also with a little bit of “no.” While the town is truly at its best in the summer months, it is still lively to visit in the Spring, Fall, and Holiday season too. Heck, we have had beach days – including going in the water! – as early as April and as late as November!

There are plenty of activities and events in the off-season, so it is likely best to plan around one of those. We have come for the garden tours in April, a trunk-or-treat event in October, and their holiday main street celebrations in December (complete with Santa and free movies at the historic theater – last year they played Home Alone and it was excellent). We also came for New Year’s Eve this year, where they dropped a decorated crab pot to ring in 2018! Does not get much more small-town-quirky than that.

The only thing to note is that business hours get a bit funky in the off-season with shops and restaurants being closed more frequently (or even fully), so it is consistently a good idea to call before heading out anywhere. Do not trust any website to be updated! We have found the January through March months to be especially slow, but if you are simply looking for some quiet time it could be ideal!

I am sure we missed some stuff – especially since new things are popping up every few months. we have a cute little bookstore in the works down the street, and I simply noticed a sign for another upcoming bakery. We hope you folks have a strong time if you ever decide to slip through Cape Charles! And if you ever see us out and about while you are visiting, please come say hello and tell us what we are missing on this list! Ha!