The historic district of Cape Charles is a lovely place to wander in the fall, with its tree-lined streets and Victorian architecture. Stop by Mason Avenue Bakery for a warm coffee and pastry, then explore local shops like The Boardwalk for gifts or Moonrise Jewelry for handcrafted accessories. Hungry? Grab a drink and a bite at the newly minted Salty Rooster. Cape Charles’ downtown area exudes small-town charm, especially during the autumn months.

Shop the length of Mason Avenue for unique souvenirs. Pop into Moonrise Jewelry for accessories crafted from fish leather—eco-friendly leather made from byproducts of the Icelandic fishing industry—or stop by Gull Hummock Gourmet Market to sample local wines and snacks.

For a more relaxed fall activity, head to Chatham Vineyards & Winery, located just outside Cape Charles. Their Church Creek Chardonnay is a local favorite, and the scenic vineyard is the perfect place to sip and enjoy the flavors of fall.

Cape Charles Distillery, voted the #1 distillery in Eastern Virginia, offers smooth and quality spirits and craft cocktails in a casual speakeasy space. Visit their new location on Mason Avenue and enjoy the local products and the history of the Eastern Shore.

For a dose of local history, stop by the Cape Charles Museum and Welcome Center. Learn about the town’s origins as a bustling railroad town and explore artifacts that tell the story of life on the Eastern Shore. In the fall, the museum often hosts special exhibits and events, making it a great indoor activity.

Fall is the perfect time to enjoy Cape Charles’ beaches without the summer crowds. Stroll along the shoreline of Cape Charles Beach, and watch the stunning sunsets over the Chesapeake Bay. If you’re looking for a more secluded experience, visit the Cape Charles Natural Area Preserve, where you can enjoy peaceful walks through the fall landscape.

The Barrier Islands Center in Machipongo offers a deep dive into the maritime history and culture of Virginia’s barrier islands, with engaging exhibits and seasonal events. Fall visitors can enjoy art workshops, lectures, and hands-on history programs, making it a great educational stop on the Eastern Shore.

The Cape Charles Natural Area Preserve covers 29 acres of forested natural communities. Stroll two boardwalks along freshwater wetlands and a rare maritime dune woodland. The trail ends with views from a bluff overlooking the Chesapeake Bay. The preserve is a habitat for the northeastern beach tiger beetle, a federally threatened species. It’s also a good place for birding year-round and more than 240 species of birds have been observed there, including migratory birds and waterfowl.

Learn how a former sheriff, his brother and their mother transformed a dilapidated lumber shop into a coastal brewpub with locally inspired beers and bites. Cape Charles Brewing Company offers 30 taps, a canning line, a full-service kitchen and a historic ambiance in the bayside town.

For a fun fall outing, visit Pickett’s Harbor Farms just outside of Cape Charles. This family-run farm offers a pumpkin patch along with a variety of fresh, local produce and seasonal activities. Another great option is Shockley Farms, where you can enjoy fresh, locally grown vegetables throughout the season. Both farms provide a great way to experience the best of fall!