Celebrate the Season on the Shore

From Cape Charles to Chincoteague, Exploring the Charms of Virginia’s Eastern Shore in Autumn

by CoVa Mag | Sep 1, 2023

Famous Sunsets.

When those cool autumn breezes finally provide some welcome relief from summer’s heat and humidity, the Eastern Shore of Virginia beckons locals and visitors alike to make the most of the season in its charming coastal towns. Fine fall weather and famous sunsets set the backdrop for exciting activities, scenic beauty, cultural events and, of course, fresh seafood as far as your fork can follow. From shopping trips to outdoor adventures and delicious dining, here are a few ideas about how to soak up all the Eastern Shore has to offer from September to December.

Outdoor Adventures
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 Refuges 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.

Shopping and Antiquing
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. Don’t miss Moonrise Jewelry’s beautiful, one-of-a-kind jewelry made of fish leather.

Festivals and Events
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 those beloved bivalves—raw, steamed, fried and more—while enjoying live music and entertainment, happening Oct. 7 this year. When the holidays roll around, you do not want to miss Festive Fridays in Cape Charles, which transforms into something akin to the set of a Hallmark Christmas movie with vendors, treats, live performers and good ol’ Saint Nick.

Historical Sites and Museums
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.

Farmers’ Markets
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 September 30. 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.

Dining and Seafood Delights
The Eastern Shore’s culinary offerings are a blend of traditional and contemporary with a strong emphasis on all things freshly caught (or farmed) in nearby waters. From Hook @ Harvey and The Oyster Farm Seafood Eatery to Mallards on 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, Irish-inspired fare at Kelly’s Gingernut Pub, eye-opening java at Cape Charles Coffee House or creamy, cool treats at Brown Dog Ice Cream.

Wine, Beer & Spirits
Gather around a fire pit with your friends and a glass of Church Creek Cab Franc at Chatham Vineyards in Machipongo, or check their schedule for Wine & Oyster Weekends in the cooler months. Craft beer and cider lovers will also find plenty brewing on the Eastern Shore. Cape Charles Brewing Company serves up pints and bites to help you fuel up and fill up this fall, and Buskey Cider on the Bay (a welcome outpost of the Richmond original) has cornered the local market on fresh, crisp brews made from 100% Virginia apples. Visitors to Cape Charles Distillery will find a sophisticated ambience to set the mood for tasting their flagship bourbon, whiskeys, moonshine and vodka.

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