The One Chesapeake Bay Town Everyone Should Visit At Least Once
Cape Charles is one of those charming places everyone needs to visit at least once in a lifetime. Founded in 1884 in Virginia’s southern tip of the Delmarva Peninsula, it quickly grew in importance as a railway hub ferrying trains across the Chesapeake Bay to Norfolk.
While the trains no longer run, you can still see some of the original tracks running through the town and a sprinkling of historic rail cars dotted around town as a reminder of its railway heritage. The railroads’ greatest legacy, though, is the many authentic Victorian-era commercial buildings and homes just steps away from the Chesapeake Bay.
Cape Charles’ Early Years
The town's origins can be traced back to Pennsylvania railroad magnates Alexander Cassatt and William Lawrence Scott, who purchased the land the town sits on for the southern terminus of their New York, Philadelphia, and Norfolk Railroad. It was certainly an ambitious undertaking, involving not just the laying of track, but also the construction of a harbor capable of handling the freight barges and passenger vessels steaming across the Bay.
Engineers were also brought in to lay out the town on a 27-block grid. Seven east-west avenues were named for Virginia statesmen, including Tazewell, Mason, Randolph, and Washington, while north-south streets bear the names of fruits that grew on the Eastern Shore. This original and well-planned layout still serves the town today, and was a contributing factor in Cape Charles's designation as a National Historic Landmark.
By 1912, Cape Charles Harbor was handling millions of tons of freight, ensuring the town’s place as the largest community on Virginia's Eastern Shore. This connection with the railroad continued right up to 1964 and the completion of the Chesapeake Bay Bridge-Tunnel, which eliminated the ferry service and triggered decades of economic decline.
That decline, though, ended up saving Cape Charles. Rather than be redeveloped or knocked down, forward-thinking townsfolk created the Cape Charles Historic District, which now helps protect one of the largest concentrations of late-Victorian and turn-of-the-century architecture on the East Coast.
Historic Downtown Cape Charles
One thing you’ll notice as you walk the streets of this delightful Chesapeake Bay town is its architectural diversity. As well as Queen Anne, Gothic Revival, and Neoclassical styles, you’ll find carefully preserved Spanish Colonial Revival and even Art Deco architectural eye-candy.
One of the best venues on the Bay, the Historic Palace Theatre is nice to look at inside and out. A staple of the town’s entertainment scene since 1942, this Art Deco theater features its original porthole glass-paneled doors and hand-painted murals.
Another must-see is the Cape Charles Museum and Welcome Center. This top-notch attraction provides a picture of Cape Charles's railroad days and its Chesapeake Bay heritage through photographs, documents, models of barges and ferries, as well as several vintage railway cars and an engine. Central Park, just a couple of blocks from Mason Avenue, is a pleasant stroll and hosts art events as well as a popular (and free) summer concert series.
Shop, Dine, Drink, and Stay on the Bay
You’ll also find the best shopping in Cape Charles along Mason Avenue and Peach Street. Bookworm or not, Peach Street Books is a one-of-a-kind shopping experience that occupies an old 1930s gas station and the neighboring 1950s service garage. Over 10,000 used and new titles are in stock at any given time, including books by local and regional authors. There’s also a café on the premises.
Gull Hummock Gourmet Market is the place to go for gourmet foods, wine, cheese, and regional food items, while Drizzles sells specialty oils and vinegars. The Boardwalk remains a perennial favorite for gifts of all kinds, and for art, Lemon Tree Gallery and Studio exhibits work from more than 100 artists. Much of the art on display is inspired by the Chesapeake Bay and the Eastern Shore.
Cape Charles is also making a name for its food and beverage offerings, too. Cape Charles Brewing Company is a must for its award-winning craft beers (go for its popular Smith Island Oyster Stout) and bar food, plus outside seating and a play area for the kids. Prefer something a little stronger? Cape Charles Distillery makes bourbon, whiskeys, vodka, and moonshine using locally grown corn and grains and Virginia mountain spring water (there’s also a tasting room).
While both the distillery and the brewery serve food, splash out on a classy Italian dining experience at Ambrogia Caffé & Enoteca. They’re also known for their extensive Virginia wine list. And no visit to the Chesapeake Bay is complete without sampling some local seafood. The Shanty, situated on the docks at Cape Charles Harbor, specializes in fresh seafood, even going so far as listing the watermen who supplied the day’s catch on the menu.
If you can make a weekend of your visit, Hotel Cape Charles is a great choice. Located downtown on Mason Avenue, the building has been a hotel for over 100 years and is within walking distance of shops, restaurants, the beach, and the fishing pier. They also rent golf carts, which you’ll see everyone zipping about in here.
Cast a Line and Dip Your Toes in the Chesapeake Bay
As you approach the Chesapeake along Mason Avenue, you’ll find the Cape Charles Fishing Pier stretching for 300 feet out over the water. It’s a must-visit for fishers looking to cast a line in the deep water of the Cape Charles Harbor Federal Channel. Fishing here is free of charge, with lighting for night fishing, and restroom facilities nearby. Common catches include flounder, croaker, puppy drum, spot, grey trout, and ribbonfish, with the best fishing typically occurring when the tide turns
The pier also provides superb views over the harbor and Cape Charles Beach. Stretching along Bay Avenue and facing west toward the Bay, the beach provides calm, shallow waters that are perfect for families. There's even a designated, roped-off swimming area at the south end of the beach.
Beach access and parking along Bay Avenue are free, and the beach is an easy walk to the downtown area. And try to stay long enough to catch a glorious sunset over the Chesapeake Bay.
Back to Nature on the Bay
The Cape Charles Natural Area Preserve protects an important coastal habitat near the town. In addition to beach, dune, and maritime forest communities on the Chesapeake Bay, the preserve is a significant stop for migratory birds and forms part of the Virginia Birding and Wildlife Trail. There’s a boardwalk that traverses several natural communities, including a rare Maritime pine forest; it ends at several benches overlooking the Chesapeake Bay.
A few miles out of town, the Eastern Shore of Virginia National Wildlife Refuge is a must-visit to learn more about the Chesapeake Bay’s flora and fauna. Positioned between the Atlantic Ocean and the Bay, millions of songbirds and monarch butterflies converge here along with thousands of raptors on their voyage south, creating one of the most important avian migration funnels in North America.
The Visitor Center features an indoor wildlife observation deck and interactive exhibits exploring local ecology, migration patterns, and the refuge's diverse habitats. There’s also a butterfly garden, and admission is free.
Chesapeake Bay Bridge-Tunnel
Its proximity to the amazing Chesapeake Bay Bridge-Tunnel (CBBT) is another great excuse to visit Cape Charles. Just 10 miles south of the town, this remarkable feat of engineering spans 17.6 miles across the mouth of the Chesapeake Bay, connecting Virginia's Eastern Shore with Virginia Beach and the Norfolk metropolitan area.
Designated one of the "Seven Engineering Wonders of the Modern World", it combines bridges, tunnels, and four man-made islands in a single crossing. Two tunnels pass beneath the Thimble Shoals and Chesapeake navigation channels, allowing large vessels to pass in and out of the bay without obstruction.
The Chesapeake Bay Bridge Scenic Overlook is where you’ll get panoramic views of both the Chesapeake Bay and the bridges as they seem to disappear in the distance (they’re actually heading into tunnels). There’s ample parking, so be sure to stop, and get ready to be impressed by the sheer scale of this massive bay.
The Chesapeake Bay Town to Visit
This American beach town will provide everything you need for a memorable Chesapeake Bay break. In addition to its immensely walkable historic downtown, Cape Charles also boasts a great public beach on the Chesapeake Bay, superb local restaurants serving Eastern Shore seafood, and plenty of opportunities to get outside and enjoy nature. Even though you’ll visit it once, odds are you’ll likely come back.
