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Fall weekend getaway: 3 perfect days at Cape Charles in Virginia

Visitors walk on the Cape Charles Fishing Pier. Photo by Parker Michels-Boyce Visitors can cast for striped bass and bluefish at the town’s fishing pier.

Tucked near the mouth of the Chesapeake Bay at the southern tip of the Delmarva Peninsula, the historic town of Cape Charles, Virginia, has gone through major transformations over the years. The once booming railroad and ferryboat depot fell into decades of hard times before finding its stride as one of the Mid-Atlantic’s most authentic, laid-back beach towns, especially for an autumn weekend getaway. 

Today, airy bed-and-breakfasts with porch swings and cold pitchers of lemonade sit near a restored downtown with eclectic restaurants, shops, and cultural attractions. Come October, the sweltering heat of summer has faded into dreamy days that are still warm enough to swim but too cool for the legions of carnivorous bugs. 

Plus, it’s migrating bird season, too. Here’s how to spend a long autumn weekend looking for dolphins, sampling spirits, and enjoying the vast expanses of a littoral paradise when nearly all the tourists have left. 

Day 1 itinerary: morning stroll along the pier, oyster shucking, and sunset cruise

The Oyster Farm at King’s Creek Marina.

The Oyster Farm at King’s Creek Marina.

Start off with an easy morning stroll south along the town’s boardwalk that lines Bay Avenue, stopping to check out the 7-foot statue of the Roman god of the sea, Neptune, installed in 2015 north of the fishing pier. Morning is a great time to cast for striped bass and bluefish. A fishing license isn’t required to fish from the pier. Pick up the gear you need at Bailey’s Bait and Tackle. Otherwise, head east on Mason Avenue, the town’s main business drag, and grab breakfast at The Almeta, a new restaurant that opened inside the Hotel Cape Charles. Try the sweet almond toast made with organic sourdough, blueberries, and toasted coconut, or go light with a mango smoothie. 

If you get tired of walking, consider renting a golf cart at CC Ryder Rentals or Eastern Shore Custom Carts. With little traffic and almost no chance of getting lost, it is the easiest (and most fun) way to get around town. Before the Chesapeake Bay Bridge-Tunnel connected the Eastern Shore of Virginia with the mainland in 1964, ferries would haul railroad cars, goods, and passengers across the bay to Norfolk. 

The Cape Charles Museum keeps those memories alive with exhibits inside a repurposed power plant. Check out the collection of ferry boat replicas or wander outside to sit inside a caboose. Ask if the museum will be hosting its annual fall oyster roast, a wildly popular community event with all you can eat oysters. 

Fresh oysters on the half shell at the Oyster Farm.

Fresh oysters on the half shell at the Oyster Farm.

Otherwise, the Oyster Farm at King’s Creek Marina overlooks oyster beds and serves oysters on the half shell harvested by local watermen. The clam chowder’s tasty, too. 

Cape Charles is one of the few places on the East Coast where you can watch the sun set over the water. Book a two-hour evening cruise with Captain Pete of Eastern Shore Boat Tours who can take you out to a “ghost fleet” of sunken ships and deploy a hydrophone to listen (and look) for dolphins. Alternatively, ask to explore the barrier islands just east of Cape Charles, where some of the longest stretches of undeveloped beaches on the Atlantic run for miles and miles with no way to see them other than by boat. 

A must: Drive an estimated 10 miles north to the Barrier Islands Center in nearby Machipongo and learn about what life was like on these islands when they were inhabited in the 1800s and 1900s. 

You may also like: Romance abounds at these Virginia bed-and-breakfasts

Day 2 itinerary: muffelettas, art viewing, and a nature walk

Fuel up on giant cinnamon rolls or the croissants du jour at Coastal Baking Co., a new pastry shop that also does biscuits and gravy and irresistible muffelettas. 

The diner inside Rayfield’s Pharmacy is also a popular spot for locals. Try the scrapple sandwich, a Mid-Atlantic specialty, with a runny egg, and note the enormous red drum (sometimes called channel bass in these parts) mounted over the grill. 

Lemon Tree Gallery and Studio.

Lemon Tree Gallery and Studio.

Cape Charles struts its artsy vibe at the Lemon Tree Gallery and Studio, where local artists such as Thelma Peterson and owner Clelia Cardona Sheppard display artwork, including watercolors, oil paintings, and sculpture. 

Look up and you’ll often spot a light aircraft circling over the marshes and bays with photographer Gordon Campbell at the helm taking pictures of the beauty below. See some of his best aerial work at the At Altitude GalleryMoonrise Jewelry bursts with unique wearables like fish leather bracelets and necklaces with freshwater pearls. 

Just down the street you’ll find Drizzles with olive oils from Italy, Greece, and Spain, along with tapenade, mustards, and sampler boxes. 

Cape Charles Natural Area Preserve.

Cape Charles Natural Area Preserve.

Take an afternoon stroll along the boardwalk of the Cape Charles Natural Area Preserve, a 29-acre refuge, to look for migrating raptors, royal terns, and great blue herons. 

Farther south at the 562-acre Kiptopeke State Park you’ll find 5.1 miles of hiking and biking trails, a fishing pier, and ample opportunities to spot hundreds of species of birds mustering their courage to fly over the open Chesapeake and continue south for the winter. 

For dinner, you can’t go wrong at the Shanty, a seafood shack on the water at Cape Charles harbor or at Kelly’s Gingernut Pub, an Irish-themed tavern and restaurant inside an old bank. Ask to sit in the vault.

You may also like: Following the wild ponies of Virginia’s Eastern Shore

Day 3 itinerary: fishing, kayaking, and local brews

Fishing trip with Marsh Madness Charters.

Fishing trip with Marsh Madness Charters.

Swing by the Cape Charles Coffeehouse for a morning parfait, a stiff cappuccino, and an earful of local gossip before heading out for a half day of fishing with Captain Zach Pfingst of Marsh Madness Charters, who’ll show you how to sight cast for speckled trout and redfish in the flats near the Virginia Coast Reserve. 

Otherwise, sign up for a guided kayaking tour with Southeast Expeditions along Church Creek to look for gulls and terns before stopping for wine and cheese at Chatham Vineyards. The company will also deliver kayaks to you for paddling along Cape Charles Beach. 

In October, the Between the Waters Bike Tour features a collection of group bicycle rides from 25 to 100 miles long that attract about 800 riders a year. 

Cape Charles Brewing Company.

Cape Charles Brewing Company.

Celebrate your efforts that evening with crab cake bites and a Cobb Island IPA at the Cape Charles Brewing Company

Tim Neville is a freelance writer for the New York Times, the Financial TimesOutside, and Men's Journal.

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