3 hours, 45 minutes
There is no well-trodden wooden boardwalk in Cape Charles. You also won’t find surfing-caliber waves. You will, however, find easygoing ripples, toddler-friendly beaches, and the most breathtakingly beautiful bay sunsets you’ve ever seen. Situated on the southern tip of Virginia’s Eastern Shore, Cape Charles is a short drive from bustling Virginia Beach, yet few have heard of it, much less strolled its tree-lined streets dotted with ornate Victorians. But this coastal gem that grew up as the last stop on a rail line is beloved by those in on the secret.
The 134-year rail history of Cape Charles came to a halt just three years ago and has since led to a growth in tourism, drawing sunseekers eager for a more relaxed summer vibe. The town may be ushering in more visitors, but is maintaining its small-town appeal. You won’t find chains of any kind here. For coffee, order a cuppa at Cape Charles Coffee House. Need some aloe after too much sun? Go to Rayfield’s Pharmacy.
This summer, a few more local boutiques and snack shops are making their debut in the historic district, like K-Coast Surf Shop and Suzy’s Old Fashioned Custard. For made-to-order sandwiches and chips, stop in at the brand-new Beach Market before spreading out your towel on Cape Charles Town Beach or laying down a picnic blanket at Central Park. The large green space there has long been a welcoming in-town fixture with benches, a gazebo, and a fountain. This year, kids will see a new zipline and ball pit to kick up the fun when not on the beach. The whimsical Cape Kids playground continues to be a favorite with little ones taking a break from the sand and surf.
Golf carts are the go-to way to get around Cape Charles, and a new historic self-guided golf-cart tour gives new reason to putter around the historic district. Pick up a tour booklet when renting from Eastern Shore Custom Carts on Randolph Avenue, just one block west of the town’s welcome center.
By the beach
It’s easy to laze the day away on the pristine Cape Charles Town Beach, listening to the gently lapping waves from Chesapeake Bay. Located on Bay Avenue, the sandy white beach is steps from the historic district and can be freely accessed at the end of every block in town.
Snap a photo with the colorful LOVE sign at the corner of Bay and Mason Avenues. Each letter of the LOVE sign reflects a separate aspect of Cape Charles: The “L” is made of seashells (beach life), the “O” is a tractor tire (agriculture), the “V” is made of two kayaks (water adventures), and the “E” is made from crab pots (fishing and, yes, crabbing).
Plan a day to visit the sandy shores of Kiptopeke State Park, but for more than just soaking in the sun. From the beach, it’s an easy quarter-mile paddle to a convoy of crumbling ghost ships that date back to World War II. These nine vessels were once used to transport wartime commodities and later served to protect a now-defunct ferry terminal from severe weather.
Wine lovers, book the Paddle Your Glass Off Tour with Southeast Expeditions. This half-day kayaking tour includes a 45-minute glide (each way) through Church Creek with a stop on the shores of Chatham Vineyards for a glass or two, maybe even a cheese board. Plus, get a behind-the-scenes look at this coastal winery.
There’s a lot more to do on the water, too, of course, like fishing, sailing, kayaking, paddleboarding, and Jet Skiing. Rent paddleboards, single kayaks, and double kayaks from Southeast Expeditions. Even better, the outfitter will deliver your human-powered watercraft of choice directly to you.
Make time to stroll historic downtown, if only for a scoop of Vanilla Chip Latte or Muddy Paws at Brown Dog Ice Cream on Mason Avenue, the main drag in Cape Charles. Walk up to the window to order a cone. The flavors change fairly often, but rest assured: You can’t go wrong with any of them.
For dinner, try The Shanty for an order of hush puppies with honey butter and a basket of fried oysters. This casual, cottage-style seafood restaurant serves up a daily catch along with live music on certain nights. It also happens to be adjacent to the marina, a spot many consider to be the very best place for a wildly colorful sunset. In late afternoon, watch as anglers come in to offload the day’s catches.
In Cape Charles, you’ll also find coastal hiking trails at Savage Neck Dunes State Natural Area Preserve. These 298 acres along a mile of pristine Chesapeake Bay shoreline include three hiking trails and unusual bayside sand dunes that reach as high as 50 feet tall. On the beach, keep your eyes open for rare northeastern beach tiger beetles that scurry across the sand to the delight of beachgoers.
In the historic district, book an Airbnb, maybe a charming old home with a harbor view that was featured on HGTV’s Beachfront Bargain Hunt. Or look to a historic beachfront inn, like the Northampton Hotel. This property was built in the early 1900s, and extensive renovations were finished in 2018. Enjoy a luxury stay in the heart of the Cape Charles historic district with winning Chesapeake Bay views.
Families, look to Cherrystone Family Camping Resort on the north end of Cape Charles. Stays range from deluxe cottages and glamping-friendly tents to classic campsites for RVs and tents. Here, you’ll find all the kid-friendly amenities, like a swimming beach, multiple pools, mini golf, and a massive lineup of daily activities, from bingo and cornhole to arts and crafts.