From Cape Charles sunsets to Chincoteague Salts, the flavor and fun on Virginia’s Eastern Shore are calling you
Photo Above By Leona Baker
Those months ending “er” are upon us, and that means cooler breezes and more spacious beaches on our many shores. Speaking of shores, The Eastern Shore of Virginia is a great place to get away (or be a tourist in your own town if you’re a Shore local) during the so-called “shoulder months” of the tourism season, when the weather is still great and there are fewer folks vying for a spot on the sand or a table at your favorite restaurant.
The Shore’s charming coastal towns from Cape Charles to Onancock to Chincoteague offer legendary sunsets, fun activities, gorgeous scenery, cultural events and, of course, enough delicious seafood to satisfy even the crabbiest of diners. From shopping trips to outdoor adventures and unique dinner dates, here are a few ideas about how to soak up all the Eastern Shore has to offer from September to December.
Get Outside and Thrive
The Eastern Shore’s natural beauty is especially magnificent in the fall, making it the perfect time for hiking, biking, birding, boating and beyond. Explore the scenic trails of the Eastern Shore or Chincoteague National Wildlife Refuge and Kiptopeke State Park. See migratory birds and other wildlife among the picturesque marshlands. Launch your own kayak from one of many available spots or sign up for a rental or guided tour with companies like Assateague Explorer Cruises & Kayaking or Burnham Guides Paddle & Bike. Charter fishing and boating are big, too, with outfits like Tidewater Charters and Top Dog Charters.
Rock the Retail Therapy
Whether you’re more of a browser or a buyer, if shopping is your bag, the Eastern Shore is for you. Antiquing enthusiasts should bring their walking shoes to Blue Crow Antique Mall in Painter to stroll 35,000 square feet of vintage furniture, clothes, toys, tools and more. Also check out Exmore’s Antique Emporium and a host of shops boasting antique nautical items like decoys. Cape Charles and Onancock are great for finding unique or handcrafted clothing, accessories, original art and home goods. Check out Moonrise Jewelry, Local-ish Art and, for the kids, Chessie’s Toys & Games and Chuckletown Productions.
Fall for the Festivities
The fall season on the Eastern Shore is alive and shucking with fun festivals and community events that celebrate the region’s unique community, history, aquaculture and more. Among the most anticipated is the Annual Chincoteague Oyster Festival, where visitors gather to savor “Chincoteague Salts”—raw, steamed, fried and more—while enjoying live music and entertainment, happening Oct. 11 this year. When the holidays roll around, you do not want to miss Festive Fridays in Cape Charles, which transforms into the set of a Hallmark Christmas movie with vendors, treats, live performers and good ol’ Saint Nick from Nov. 28 through Dec. 19.
Make a Little History
History buffs will find themselves enchanted by the Eastern Shore’s rich heritage and well-preserved historical sites. Pay a visit to the Cape Charles Museum and Welcome Center to learn about the town’s intriguing past and its significance as a railroad terminus. Step back in time at the Barrier Islands Center in Machipongo, which houses exhibits on the unique culture of the Barrier Islands and its brave inhabitants. Some other historic destinations include the Assateague Lighthouse, Eastern Shore Maritime Museum, Ker Place and the Museum of Chincoteague Island.
Savor Homegrown Goods
Fall is harvest season, of course, and Virginia’s Eastern Shore is known for its famed, farm-fresh veggies almost as much as its seafood. And what better way to experience that local farmers’ markets? Take your pick of just-harvested fruits, vegetables and artisanal products. Sample homemade apple cider, freshly baked pies and locally crafted cheeses. The Onancock Market is open Saturday mornings through November, while Chincoteague Island Farmers and Artisans Market is rolling through October 25. Or visit Pickett’s Harbor Farm near Cape Charles for gorgeous greens, butter beans, those famous Hayman sweet potatoes and, if the weather cooperates, beautiful Brussels sprouts.
Dine Like a Local
The Eastern Shore’s culinary offerings are a blend of traditional and contemporary with a strong emphasis on all things freshly caught or farmed. From Hook @ Harvey and The Shanty to Mallards at the Wharf and Bill’s PRIME, you can treat yourself to a seafood feast and, in many cases, a stunning waterfront view to match. But there’s also lots to choose from for an array of palates. Find great pizza at Deadrise Italian Kitchen, elevated pub fare at the new E&O Pub, eye-opening java at Cape Charles Coffee House, old-school comfort food at Exmore Diner, or creamy, cool treats at Brown Dog Ice Cream.
Wine, Beer & Spirits
Gather around a fire pit with your besties and a glass of Church Creek Chardonnay at Chatham Vineyards in Machipongo, or check their schedule for live performers on tap in their Crush Pad Music Series. Craft beer and cider lovers will also find plenty brewing on the Shore. Cape Charles Brewing Company serves up pints and bites to help you fuel up and fill up this fall. Also a don’t-miss for discerning drinkers is the recently relocated Cape Charles Distillery, featuring a distinctively sophisticated and moody ambience complete with a killer rooftop view for tasting their flagship bourbon, whiskeys, moonshine and Woo Woo vodka.
100th Chincoteague Pony Swim
HISTORY ON HORSEBACK
A cherished local tradition a century in the making celebrated an incredible milestone this year. The 100th Annual Chincoteague Pony Swim in Chincoteague, Virginia, on the Eastern Shore took place on July 30, 2025, and was part a weeklong celebration that included the Pony Penning, Pony Auction, Fireman’s Carnival and more. Shown here, Saltwater Cowboy Tom Newman (top) and the ponies swimming from Assateague Island to Chincoteague Island (bottom).
