For the 50+ Traveler

Captain John Smith explored the Eastern Shore of Virginia around 1607 and discovered a long peninsula with a gentle bay on the west side and the Atlantic Ocean on the east. The fertile land, shallow water, and tidal flats confirmed the area as a jewel for commerce. Sailing ships began transporting the region’s seafood and vegetable bounty to the colonies up the coast.

It wasn’t until the railroad was extended from Pocomoke City, Maryland, in 1884, however, that Cape Charles became one of the most prosperous regions in the United States. Barges transported railroad cars and ferries carried people across the Chesapeake Bay to Norfolk, Virginia. After World War II, automobiles were all the rage, and passenger rail service ended by 1958. In 1964, the 23-mile Chesapeake Bay Bridge-Tunnel was built to connect Cape Charles to mainland Virginia, making the trip more comfortable and faster than the long ferry ride.

Today the peninsula is known as the Delmarva -- a combination of the names Delaware, Maryland, and Virginia -- since it extends through three states. The Virginia portion is 70 miles long and is divided into three separate areas: the Upper, Middle, and Lower Shores. Cape Charles is located on the Lower Shore. While the charming city has had its fair share of economic ups and downs, it is currently experiencing a renaissance. Known for its pristine beach, historic town, and relaxed vibe, Cape Charles makes for a perfect long weekend escape.

Things To Do In Cape Charles

There are so many things to do in the small town of Cape Charles. The surrounding waters offer opportunities for fishing and sailing charters, Jet Skiing, paddleboarding, and kayaking. The gentle waves on Cape Charles Beach are perfect for a dip or a day spent sunbathing on the soft, white sand. Just steps away is the free public fishing pier, and both are within walking distance of Mason Avenue, the shopping district.

In town, you’ll discover art galleries and eclectic shops selling artisan jewelry, clothing, and home decor. When hunger strikes, there are a variety of eateries for breakfast, lunch, and dinner. Sip a beer, cider, or a handcrafted spirit made from local ingredients. The town is small enough that you can rent a golf cart to see it all.

If you are a golfer, you can play a round or two at Bay Creek, where you can choose between a Nicklaus-designed course and a Palmer-designed course. If you love history, stop at the visitor center to learn about the Eastern Shore’s past, and make time to stroll around town and admire the beautiful architecture, including 20th-century revival homes, bungalows, and late Victorian homes.

A kayak tour with SouthEast Expeditions.
Jeanine Consoli

Take A Tour With SouthEast Expeditions

SouthEast Expeditions has more than 20 years of experience operating tours on the Eastern Shore. Recognized by The New York Times and dozens of other publications, SouthEast Expeditions offers unique tours including winery tours by kayak -- the perfect way to spend a day in Cape Charles.

Our expert guide, Nick, explained how to steer our single kayaks, and we took a leisurely paddle along Church Creek from the wharf in Bayford to the Chatham Vineyards. Along the way, we observed low-flying herons and fishermen hoisting their bounty from the shallow waters. Our small group explored the historic Chatham Vineyards property and enjoyed a delicious wine tasting, including our choice of a bottle of wine (for every two paddlers).

The experience took 2.5 hours total and is perfect for beginners, nature enthusiasts, and wine lovers. It can be challenging to get in and out of the kayak, however, so if you have back issues, this tour may not be for you. SouthEast Expeditions also offers bikes, stand-up paddleboards, and kayaks as daily or weekly rentals.

A golf cart rental in Cape Charles.
Jeanine Consoli

Rent A Golf Cart And Cruise Like A Local

Golf carts are the way to get around in Cape Charles, and it’s a fun way to get from town to the beach or to sightsee in the historic district.

C.C. Ryder Rentals is located on Mason Avenue. You can't miss this small business, because you get a free beer with your rental! The website reads, “I guess legally, I can’t give you the keys and hand you a beer, but on return, if I’ve got one here, we’ll kick back on the porch.” That’s why owner Steve Smith has so many five-star reviews -- he’s willing to go above and beyond for his clients. He charges reasonable rates for his late model carts for the afternoon, 24 hours, or the week.

Buy Some Tackle And Go Fishing Off The Free Pier

Bailey’s Bait & Tackle has been in business for 51 years. Their motto is and always has been that the customer comes first. They can supply all your fishing needs right in the shop. If you are a first-timer, look for the inexpensive rods, reels, and string sets for as low as $21. If you don't have your own gear, you can buy some equipment and walk (or ride) to the free fishing pier at the end of Mason Avenue. You don't need a license to fish off the dock, since the town has covered the cost. Get ready to write your own big fish story!

The Cape Charles Museum and Welcome Center.

Discover The History Of Cape Charles

If you love history, stop at the Cape Charles Museum and Welcome Center. Did you know that an impact crater was formed by an asteroid 35 million years ago around Cape Charles? It landed right in the Chesapeake Bay. You’ll learn about this and more at the museum. Look for the exhibits related to the historic railroad and ferry service, including replicas and artifacts from the period. There are also special exhibits that change regularly. When you visit, don’t forget to pick up the brochure featuring a self-guided walking tour of the historic district.

At Altitude Art Gallery in Cape Charles, Virginia.
Jeanine Consoli

Visit An Art Gallery

Ever wish you could get a bird’s-eye view of a beautiful place? Visit At Altitude Gallery, the only known gallery to feature aerial photography exclusively. At Altitude, you will discover the work of aerial photographer Gordon Campbell, whose stunning images of Cape Charles (and other locations) are printed on ChromaLuxe photo panels. These are vibrant photos with incredible dimension.

Mason Avenue features two other fine art galleries: the LemonTree Gallery and the Ellen Moore Gallery.

Hit The Links

Bay Creek is a private golf club that offers visitors a few different ways to play a round on their Nicklaus or Palmer course. If you choose to rent a condo at Bay Creek, you can play as a resort guest. Additionally, several hotels and bed and breakfasts around town have partnership agreements with the clubhouse. If you arrive by boat and rent a slip at the marina, you can also reserve a tee time. The courses are challenging, but some holes offer spectacular views of the Chesapeake.

The Coastal Baking Co. in Cape Charles, Virginia.
Jeanine Consoli

Best Restaurants In Cape Charles

For a small town, there are some excellent dining options in Cape Charles. Some are housed in renovated historic buildings on Mason, and a few are on the shore of the bay. Dinner at a bayside restaurant offers a chance to catch a glorious view of the spectacular sunset. With the Chesapeake’s bounty being just steps away, many of the menus feature fresh seafood and shellfish, including native oysters and clams. But there are plenty of options for any type of food, from pizza to ice cream. Just like everything else on Cape Charles, the restaurant dress code is relaxed, even if the cuisine is five star.

Coastal Baking Co.

The Coastal Baking Co. is a fantastic way to start your day. Along with classic bakery items like bread, cakes, and pies, you can get breakfast between 8 a.m. and 10:30 a.m. If you are a fan of Southern-style biscuits, the ones here are not to be missed. Order them with ham and marmalade, with sausage gravy, or with a side of sausage. If you prefer sweeter items, they sell massive cinnamon rolls, muffins of all kinds, and specialty croissants like almond and praline.

Lunch is served after 10:30 a.m. and includes several sandwich options on bakery bread, casseroles, and entrees like Cajun gumbo. The patio offers open seating.

Whatever time you choose to stop by, get yourself a slice of the coconut cake. It’s heavenly.

Cape Charles Brewing Company

Cape Charles Brewing Company is a casual brewpub with tasty beer and delicious food for lunch or dinner. A small business owned and operated by the Marshall family, the brewing company is committed to making your experience a memorable one. The menu offers burgers and sandwiches featuring everything from ahi tuna to pulled pork, plus starters like their award-winning clam chowder. Entrees include fish and chips, steak frites, and surf and turf with shrimp and sirloin.

The beer menu is extensive, featuring everything from hop-forward drafts to ales, wheats, pilsners, porters, and stouts. Wine lovers have options by the glass or bottle, including selections from the local Chatham Vineyards.

Don’t miss the soft pretzel with the signature beer cheese and Dijon mustard -- it pairs perfectly with the beer.

The Oyster Farm At Kings Creek

The Oyster Farm at Kings Creek is an Eastern Shore favorite for waterfront dining in Cape Charles. The chefs use fresh seafood and local ingredients to prepare unique water-to-table entrees that never disappoint. Its location on the marina provides views of the magnificent sunsets over the Chesapeake Bay. Dinner dress is casual, but the quality of the food and cocktails is top notch.

Order a cup of the crab soup simmered with sherry, brandy, and cream -- it’s out of this world.

Mason Avenue in Cape Charles, Virginia.
Jeanine Consoli

Where To Shop In Cape Charles

To find some excellent shopping, walk along Mason Avenue. There are a variety of shops offering one-of-a-kind finds.

Moonrise Jewelry, just off Mason, is famous for exotic pearls and wearable art created right on the Eastern Shore. Voiajer sells unique artisan-made products, fair-trade goods, and gifts for a cause.

Periwinkles is an award-winning consignment and artisan boutique that offers upscale women’s clothing, accessories, home decor, and handmade products by local artisans.

Peach Street Books, housed in a quaint, converted garage, is the place to find new and used titles for your next beach read.

Best Places To Stay In Cape Charles

There are many accommodations in Cape Charles, from campsites and bed and breakfasts to inns and boutique hotels.

The Cherrystone Family Camping Resort has more than 700 campsites with either cabins or RV rentals right on the property. It boasts tons of amenities, including a beach just for dogs.

Chesapeake Properties has a portfolio of vacation rental accommodations, from cottages to waterfront estates.

Bay Creek offers home and townhome rentals that include golf privileges at their Nicklaus and Palmer courses.

Hotel Cape Charles is a boutique hotel in the center of town with 22 modern rooms; some have balconies with stunning harbor views.

The Cape Charles Bed and Breakfast Association will point you to all the inns and bed and breakfasts in and around Cape Charles.

What To Know Before You Go

Cape Charles is a special place where the pace is slow and hospitality abounds. The best time to visit is April through early June and September through early November. It can get sweltering by the end of June and into July and August, but if you like hot weather, there is no shortage of things to see and do then, and plenty of events and festivals take place all year long. Cape Charles is a slice of heaven, no matter when you plan to visit.