The journey across the Chesapeake Bay Bridge-Tunnel alone is worth the drive to this quaint beach town on Virginia’s Eastern Shore. The 17.6-mile engineering marvel begins in Virginia Beach, and, once you’re on “Shore time,” it’s less than 20 minutes to the picturesque town of Cape Charles, known for its adorable shops, free public beach, and colorful golf carts zipping about.
Explore Mason Avenue
Get to know the town and the locals with a casual stroll along Mason Avenue. Start at Peach Street Books, a delightfully charming bookstore housed in a storybook building with a blue roof and shutters. Grab a latte and a bagel, then browse a curated selection of new and used books for adults, children, and everyone in between.
People are also reading…
From there, peruse locally crafted wearable art at Moonrise Jewelry, known for its eco-friendly fish leather products and gold or silver cuffs featuring a map of the Eastern Shore. The shop donates 15% of each cuff purchase to Machipongo’s Barrier Islands Center, a museum showcasing Virginia’s unique coastal history and the people — watermen, artisans, farmers, scientists, innovators — who love the land. Next, visit At Altitude Gallery to admire detailed aerial photographs of Virginia’s waterways and towns, along with beautiful scenes from neighboring East Coast states. Sharing the space is North Street Market, offering a tempting selection of gourmet foods and wines, along with infused olive oils and vinegars.
Savor local seafood
A visit to the Shore is sure to inspire cravings for fresh seafood and sweeping water views. Fortunately, there are a couple of great places to satisfy both. The Shanty is a casual favorite overlooking Cape Charles Harbor, serving the usual suspects — fry baskets, rice bowls, and tacos — alongside local specialties like Virginia blue crab dip, Virginia lump crab cakes, and Hungars Creek oysters.
Speaking of oysters, they’re practically a must at The Oyster Farm at Kings Creek where you can enjoy them raw with cocktail sauce, horseradish, and mignonette or chargrilled with garlic-herb butter. Dinner may include Chesapeake flounder and crab or a land-based favorite like Steak Diane. It’s also one of the area’s best spots to catch the evening sunset.
Paddle your glass off
Looking to experience wine and water all at once? Book an afternoon Chatham Vineyards Kayak Winery tour with SouthEast Expeditions. Paddlers cross the calm waters of Nassawaddox Creek before entering Church Creek along the banks of Chatham Farm, home to picturesque Chatham Vineyards & Winery. After a leisurely tasting flight, each couple or pair of paddlers is welcome to take a bottle to enjoy on the return trip or later on at home. The winery also offers snacks, including cheese plates and local baked bread, to purchase.
Cool off in the sweetest way
A trip to Cape Charles simply isn’t complete without a stop at Brown Dog Ice Cream, a small-batch ice cream shop churning out both traditional and inventive flavors while incorporating locally sourced ingredients whenever possible. Recent collaborations have included Mason Avenue Bakery’s chocolate chip cookies, coffee ice cream featuring Eastern Shore Coastal Coffee, and a lemon curd flavor created with Deadrise Italian. They’ll always have your favorite chocolate and vanilla, but don’t be afraid to step outside the box with options like beet mascarpone with orange zest and poppy seeds.
Stay more than a day
Situated just blocks from the beach and conveniently on Mason Avenue among shops and eateries, Hotel Cape Charles is a modern boutique hotel with small-town charm and coastal vibrancy. Along with being in the center of it all, the hotel offers perks including golf cart and complimentary bicycle rentals, beach towels and chairs, and excursion lunches to enjoy on the go. Its on-site cafe, The Almeta, serves locally roasted coffee and healthy breakfast fare.
End with this hidden gem
Before heading back home (if you must), spend a little time immersed in the natural beauty the Eastern Shore is known and loved for at the Savage Neck Dunes Natural Area Preserve, less than 20 minutes outside town. Across the 298-acre preserve, wander through beach, dune, and maritime forest habitats while listening for migratory songbirds. The preserve is also home to the largest population of northeastern beach tiger beetles, a globally rare and federally protected sand-colored beetle marked with black swirls that inhabits wide, undisturbed beaches. To protect this unique species, sand disturbance — including digging by visitors or their dogs — is prohibited.
