Fall for Cape Charles: an off-season guide to our corner of the Eastern Shore

Cape Charles is more than just a summer hideaway. When the temperatures cool off, Cape Charles is still here, businesses bustling, golf carts rolling, and adventures awaiting. We’re here to tell you all of the reasons you should visit Cape Charles in the off-season.

Avoid the crowds: Hate waiting in lines? Traveling to Cape Charles in the off-season ensures you will have first-class access to the town. Don’t worry about calling ahead for dinner reservations, how long the check out line is at your favorite store, or getting to the bakery early. Just show up and revel in the greatness of a blissfully uncrowded Cape Charles.

The beach never closes: The water may not be a comfortable temperature for swimming, but our beautiful beach still offers an escape. Stroll around looking for shells, go on a beach run, or watch one of our spectacular sunsets to soak in our sandy coastline. The beach isn’t just for swimming, make it yours!

Year-long events season: You might know us for our Saturday night concerts in the park, annual Crab Slam, or July 4th celebration, but did you know we have unforgettable events all year long? In October, Dock Dogs brings tail-wagging, high-flying fun to town as our furry friends compete to win a tournament. At the end of October, our spooky secrets come alive as Cape Charles is haunted at the Halloween Hootenanny. November brings holiday spirit when Festive Fridays begin, four consecutive Friday nights of holiday fun on Mason Avenue. February highlights Love the Locals Week, a week of specials, promotions, and discounts at local businesses. And in April, join us for our annual LOVE Run, featuring a 10K, 5K, and 1-mile color run. Not to mention all of the fantastic events our businesses put on!

Observe unique wildlife: The early fall is the best time to see wildlife on the Eastern Shore of Virginia. Witness the fall migration of hawks, falcons, herons, egrets, and more from one of our nearby nature preserves. And as winter settles in, stick around to see cold-weather waterfowl like snow geese, tundra swans, or bufflehead ducks.

The opportunities are endless: No matter where your interests lie, Cape Charles has something for everyone! Outdoorsy? Try kayaking through our marshland, touring Fisherman’s Island, or hopping on a fishing charter. Girls trip? Head over to Chatham Vineyards and Winery or shop the local boutiques in our Historic Shopping District. Need fun for the whole family? Grab dinner at Cape Charles Brewing Company, see a show at the Historic Palace Theatre, or simply cruise around town on a golf cart.

Fall in Cape Charles just has a certain type of charm to it. From scenic backroads to breezy mornings on the porch, the off-season in Cape Charles offers unrestrained access to all the Eastern Shore has to offer. Stay a while in Cape Charles and discover what makes our town special year-round.

From fine dining to landscaping, Cape Charles business owners go above and beyond to provide guests and clients with top-notch experiences. This town is made special not by the individual items we procure, but how we use them to create the perfect seaside dish, exquisite spirits, a cozy place to stay minutes from the beach, or a unique display of locally-inspired merchandise. In Cape Charles, everyone is treated like family, precisely why our tiny town of 1,200 boasts 66 winning businesses and organizations across Virginia Living Magazine’s Best of Virginia campaign and Coastal Virginia Magazine’s Best of the Eastern Shore campaign. Oh, and not to mention that the town of Cape Charles won Overall Gold for Best Weekend Getaway in Coastal Virginia Magazine’s Reader’s Choice Awards.

Browse our list of winners & plan your next getaway to Cape Charles!

Best of Virginia Winners via Virginia Living Magazine:

Bailey’s Bait & Tackle : Silver Best Sporting Goods or Outdoor Outfitter

Barrier Islands Center: Gold Best Annual Charity Event (Oyster Roast), Gold Best Museum, Bronze Best Art Event (Art & Music on the Farm)

Bay Creek: Bronze Best Resort, Bronze Best Golf Course

Bay Haven Inn: Bronze Best Bed & Breakfast 

Bayside Chiropractic Rehabilitation & Laser: Bronze Best Chiropractic Practice 

Blue Heron Realty: Gold Best Real Estate Firm

Brown Dog Ice Cream : Silver Best Ice Cream Shop

Cape Charles Beach : Bronze Best Tourist Attraction, Bronze Best Family Entertainment 

Cape Charles Brewing Company: Silver Best Brewery 

Cape Charles Distillery: Gold Best Distillery, Silver Best Cocktails

Chatham Vineyards: Bronze Best Winery 

Chuckletown Productions: Silver Best Children’s Store

Deadrise Italian Kitchen: Gold Best Pizzaria 

Eastern Shore Dog: Silver Best Dog Training Company

Edible Picasso: Silver Best Vegan, Vegetarian, or Gluten Free Fare

Gull Hummock Gourmet Market: Gold Best Specialty/Gourmet Food Shop, Bronze Best Wine Shop 

Historic Palace Theatre: Bronze Best Performing Arts Theatre 

Hook @ Harvey: Silver Best Fine Dining

Jeff Klingel Landscape Design: Silver Best Landscape Design

Kiptopeke State Park: Silver Best State Park 

LemonTree Gallery and Studio: Silver Best Entertainment for Adults

Peach Street Books: Silver Best Bookstore 

The Shanty: Gold Best Seafood Restaurant, Bronze Best Outdoor Dining

Best of the Eastern Shore Winners via Coastal Virginia Magazine:

A1 Seafood: Gold Best Seafood Market 

AJ’s Bar & Grill: Gold Best Casual Eatery, Gold Best Place for Oysters, Gold Best Nightlife, Silver Best Cocktails 

Ambrogia Caffè & Enoteca: Gold Best Dinner (Tie), Gold Best Restaurant Overall, Silver Best Wine Selection 

At Altitude Gallery: Bronze Best Art Gallery, Bronze Best Art Store 

Bailey’s Bait & Tackle: Gold Best Bait and Tackle Store, Gold Best Outdoor Sporting Store 

Barrier Islands Center: Gold Best Historical Attraction, Gold Best Museum, Silver Best Kid-Friendly Attraction

Bay Creek Resort: Gold Best Resort 

Bay Creek Realty: Silver Best Real Estate Agent (Linda Buskey)

Bay Creek Vacation Rentals: Bronze Best Vacation Rental Company (Tie)

Bay Haven Inn: Gold Best Bed and Breakfast 

Beach Market: Bronze Best Seafood Market 

Brown Dog Ice Cream: Gold Best Ice Cream Shop 

Blue Heron Realty Co: Silver Best Real Estate Company 

Buoy 56: Gold Best Women’s Boutique 

Cape Charles Brewing Co: Gold Best Winery/Brewery/Distillery, Silver Best Outdoor Dining, Silver Best Nightlife 

Cape Charles Candy Co: Gold Best Candy Store 

Cape Charles Coffee House: Gold Best Breakfast, Gold Best Coffee, Silver Best Brunch 

Cape Charles Distillery: Gold Best Cocktails, Bronze Best Winery/Brewery/Distillery 

Cape Charles Fishing Adventure: Bronze Best Fishing Guide/Charter (Tie)

Cape Charles Main St: Gold Best Event/Festival (Festive Fridays)

Cape Charles Marina: Gold Best Marina 

Cape Charles Mini Golf: Gold Best Kid-Friendly Attraction  

Cape Charles Museum: Silver Best Historical Attraction, Silver Best Museum

Cape Charles Tiny Livin’: Bronze Best Wedding Venue, Bronze Best Hotel/Motel

Cape Charles Vacation Rentals: Silver Best Vacation Rental Company (Tie)

Chatham Vineyards & Winery: Silver Best Winery/Brewery/Distillery

Chesapeake Bay KOA: Bronze Best Campground  

Chesapeake Properties: Gold Best Real Estate Agent (Kim Starr), Gold Best Real Estate Company, Gold Best Vacation Rental Company (Tie), Bronze Best Real Estate Agent (Eva Noonan)

Chessie’s Toys &  Games: Gold Best Toy Store 

Chuckletown Productions: Gold Best Gift Shop, Bronze Best Toy Store

Citizens for Central Park: Silver Best Event/Festival (Concerts in the Park)

Coastal Baking Co: Bronze Best Bakery 

Coldwell Banker Harbour Realty: Silver Best Real Estate Company (Tie)

Cowlick’s Creamery: Bronze Best Ice Cream Shop 

Cravings Grab-N-Go: Silver Best Lunch

Deadrise Italian Kitchen: Gold Best Pizza, Silver Best Casual Eatery, Bronze Best Dinner 

Drizzles: Silver Best Gourmet/Specialty Foods Store 

Edible Picasso: Gold Best Lunch, Bronze Best Casual Eatery 

Fig Street Inn: Silver Best Bed and Breakfast 

Grant’s Grinds: Bronze Best Coffee 

Gull Hummock: Gold Best Wine Selection, Gold Best Gourmet/Specialty Foods Store 

Historic Palace Theatre: Gold Best Place for Live Entertainment 

Hook @ Harvey: Gold Best Dinner (Tie), Silver Best Restaurant Overall, Silver Best Waterfront Restaurant 

Hotel Cape Charles: Gold Best Hotel/Motel

K-Coast: Gold Best Surf/Skate Shop

Kiptopeke State Park: Gold Best Hiking Spot, Silver Best Place for Birding, Silver Best Campground

Lemon Tree Gallery and Studio: Gold Best Art Gallery, Gold Best Art Store 

Live Local-ISH: Silver Best Vacation Rental Company (Tie)

Local-ISH Art: Silver Best Art Gallery, Silver Best Art Store, Bronze Best Home Goods/Decor

Love Letters: Silver Best Consignment Store, Silver Best Women’s Boutique 

Love Sign: Gold Best Place for Photos; Most Instagrammable 

Mason Avenue Bakery: Gold Best Bakery 

Mimosa Barn: Silver Best Wedding Venue 

Moonrise: Gold Best Jewelry Store 

Poseidon Watersports: Silver Best Water Sport Rental Company 

SHO-NUF Sportfishing: Silver Best Fishing Guide/Charter

Southeast Expeditions: Gold Best Kayak Rental Company, Gold Best Water Sport Rental Company, Silver Best Tour Company 

Sun Outdoors Cape Charles: Gold Best Campground 

Sunset Beach Resort: Bronze Best Resort 

Table & Tonic: Silver Best Gift Shop, Silver Best Home Goods/Decor

Tidewater Charters: Gold Best Fishing Guide/Charter, Gold Best Tour Company 

The Boardwalk: Gold Best Home Goods/Decor, Silver Best Toy Store, Bronze Best Gift Shop 

The Northampton Hotel: Gold Best Brunch, Silver Best Hotel/Motel, Silver Best Breakfast

The Oyster Farm: Gold Best Wedding Venue, Silver Best Place for Oysters, Silver Best Marina, Silver Best Resort, Bronze Best Farmers Market, Bronze Best Seafood Restaurant, Bronze Best Waterfront Restaurant 

The Shanty: Gold Best Outdoor Dining, Gold Best Seafood Restaurant, Gold Best Waterfront Restaurant, Bronze Best Event/Festival (Crab Slam), Bronze Best Cocktails 

Top Dog Charters: Bronze Best Fishing Guide/Charter

Vance’s Furniture Store: Gold Best Furniture Store 

Posted August 7, 2025 by Allie Etheridge

Visit the LOVE sign. Head to the town’s beachfront at the intersection of Bay Avenue and Mason Avenue to check out Cape Charles’ famous LOVE sign, creatively composed of materials that reflect what the Eastern Shore is all about — from a tractor tire to kayaks. After you take a family photo, your kids will love climbing on the letters!

Go shell-hunting on the Barrier Islands. Taking a boat ride is thrilling in itself, but the shells you’ll find at your destination will give your kids a souvenir they’ll treasure for the rest of their lives.

Search out the Little Free Libraries. Because kids need beach reads, too! You’ll find at least three of these free library boxes around town, including one conveniently situated on Bay Avenue right beside the beach.

Rent jet skis. Got an adrenaline junkie in your family? Older kids will love the thrill of racing across the Chesapeake Bay on a jet ski. You’ll find local rentals available through Poseidon Watersports at the Town Harbor. 

Go shopping on Mason Avenue. With a candy store, kids’ store, and welcoming boutiques stocking plenty of toys and games, Mason Avenue is just as fun for kids as it is for their parents.

Take a carriage ride. Golf carts may be the preferred mode of transportation in Cape Charles, but if you’re looking for something a little bit different, try a carriage ride. Your family will love the feeling of going back in time while traversing city the historic district by horse and buggy.

Man and little boy riding a jet ski on the sea

With charming Cape Charles as your home base, here are five off-the-grid excursions where you can explore and make memories with your nearest and dearest.

Pretend that you’re on a deserted island at Savage Neck Dunes. This natural area preserve, a few minutes north of town feels like a world away. Savage Neck Dunes is known for its outstanding Chesapeake Bay beach, dune, and maritime forest communities, with three trails winding through nearly 300 acres. Look for rare migratory songbirds, tiger beetles, or just search for shells on your own quiet stretch of sand.

Kayak alongside the Ghost Ships at Kiptopeke. Head to Kiptopeke State Park for one of the most unique experiences on the Shore: kayaking or stand-up paddleboarding around nine partially sunken concrete ships known as the Ghost Fleet. You’ll often see dolphins as well as migratory and nesting birds around the ships. You’ll need to bring your own kayak or paddleboard.

Take a hike through the Cape Charles Natural Area Preserve. Craving a break from the beach? Discover the beauty and tranquility of the maritime loblolly pine forest at this natural preserve just outside of Cape Charles. A wide boardwalk leads you through several natural habitats on the way to an overlook beside the Bay. 

Look for birds at the Eastern Shore of Virginia National Wildlife Refuge. The location of this Eastern Shore refuge — right at the tip of the Delmarva Peninsula — creates a unique migration funnel for birds that results in some spectacular bird-watching, particularly in the fall. Stop by to see millions of songbirds, raptors, and butterflies converge as they fly south.

Explore the gardens of Eyre Hall. Mosey through some of the oldest gardens in the country, dating back to 1800. You’ll find ancient boxwood and gnarled crape myrtles towering over winding paths surrounded by brick walls brought as ballast from England. Allow yourself to be transported to another time as you’re drawn deeper into the gardens — we all could use a bit of healthy escapism now, couldn’t we?

When you’re craving a drink in Cape Charles, your biggest challenge may just be choosing between all of the options that local businesses have on offer. Whether your preferred beverage is coffee, beer, or moonshine, there’s sure to be an option to wet your whistle. Here are a few of the best things to drink in Cape Charles.

Packages of coffee placed on a shelf in store

Coffee from Eastern Shore Coastal Roasting Co. Start your day with a healthy jolt of caffeine from the Eastern Shore’s favorite coffee roasters. ESCR specializes in ethically grown products that are custom blended and roasted to order. Pick up a bag to make at home at Gull Hummock Gourmet Market, or grab a freshly brewed cup at Peach Street Books.

Beer at Cape Charles Brewing Co. Named one of Virginia’s best breweries by readers in Virginia Living’s annual Best of Virginia poll, Cape Charles Brewing Co. is a family-run business with an impressive line-up of brews. Choose from locally inspired options like the Assateague Island IPA, Smith Island Oyster Stout, and Bayside Belgian Farmhouse Ale. 

Close-up view of two glasses of beer and two plates of French fries and sausages on a restaurant table outside
Close-up view of three colorful cocktails placed on a bar

Cocktails at Cape Charles Distillery. You don’t have to leave the Shore for an upscale cocktail bar experience — Cape Charles Distillery offers top-notch cocktails made with hand-crafted local spirits. Grab a seat in their always-bustling tent for a craft cocktail, or pick up a bottle of their flagship bourbon, whiskeys, moonshine, or vodka. It’s no wonder they won Best Distillery and Best Cocktails in Eastern Virginia in Virginia Living’s 2024 Best of Virginia poll.

Wine from Chatham Vineyards. Take a little road trip to scenic Chatham Vineyards, located just a few miles north of Cape Charles. This working farm has been in operation for four centuries, most recently serving as a high-density, European-style vineyard. Would you rather arrive by water? Book a spot on Southeast Expedition’s “Paddle Your Glass Off” kayak tour for a relaxing creek paddle that ends at the vineyards.

There are so many different ways to explore Cape Charles — and one of our favorites is driven by the tastebuds.

This small town offers an impressively robust culinary landscape, with unique flavors that you’ll find only on our little slice of the Eastern Shore. Stick with us, and we’ll show you how to get to know Cape Charles through some of its most delectable food.

Female pastry chef in front of three pieces of cake placed on cake holder

Start the Day with Something Sweet. A busy day at the beach requires proper fuel, so treat yourself to an indulgent pastry from one of our bakeries — or sit down to a full breakfast. Mason Avenue Bakery, and Coastal Baking Co. have been known to see lines out the door as happy customers wait patiently to get their fix of scones, sticky buns, and muffins.

For a sit-down experience, grab a seat on the patio at the Cape Charles Coffee House for pancakes and prime people-watching, or head to Rayfield’s Pharmacy for a budget-friendly breakfast with the locals. Don’t miss out on the latest addition to the Cape Charles breakfast and lunch scene – The Northampton Hotel – offering homemade specialties on the porch or inside! Attached to the lobby of the Hotel Cape Charles, Sonny’s is a newer addition to the local scene that offers specialty lattes, breakfast sandwiches, and more filling plates ranging from the virtuous (avocado toast) to the indulgent (like the banana pudding waffle). 

Don’t Skimp on Lunch. How does a picnic on the beach sound? Or maybe a leisurely lunch overlooking the water is more your style? These are just a few of the tough choices you’ll be faced with when midday arrives on the Eastern Shore. The Shanty is a top-rated local spot for lunch (and dinner, for that matter) thanks to one of the best views in town and an extensive menu spotlighting local seafood (think blue crab dip and fried local oyster baskets). Stop by Kelly’s Gingernut Pub for classic Irish cuisine in a cozy setting, or return to any of our recommended breakfast spots for equally enjoyable lunchtime fare. Both Cape Charles Coffee House and Rayfield’s Pharmacy switch over to their lunch menus midday with classic options like wraps, sandwiches, and burgers. If you are looking for award-winning sandwiches? Head over to Cravings for amazing sandwiches! Right on the edge of town, Cape Charles Brewing Company serves lunch daily in their spacious tasting room or out on the expansive lawn — the Brew Daddy Burger, topped with bacon, caramelized onions, and dripping with beer cheese, is legendary.

A Dinner to Remember. For authentic Italian cuisine and a romantic vibe, visit Ambrogia Caffe & Enoteca. Or wrap up your day with a view of the water — The Shanty, Hook @ Harvey, and The Oyster Farm Seafood Eatery are all waterfront spots known for their fresh seafood and sunset views. Head over to Aj’s Bar and Grill for the ultimate elevated sports bar cuisine! Voted the best burger on the Eastern Shore by the Local’s Choice 2024! If you’re craving some homestyle classics, visit Salt and Sand. The entire family will thank you! Or order some pizza from Deadrise Italian Kitchen to-go and take your pizza party right to the beach!

Close up of a restaurant table with two dishes, with harbor in background

In the warmer months, a cone from Brown Dog Ice Cream, Chases, Rayfields, or frozen custard from Cowlicks Creamery is the ideal way to cap off a day of dining out on the Cape Charles.

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