The Weekender: Cape Charles

Spend some time winding down on the Eastern Shore.

Where to stay, what to do and where to find good things to eat for a weekend in charming Cape Charles.


Retreat Indoors

Fig Street Inn, 711 Tazewell Avenue

This boutique-style bed and breakfast opened in 2011 after owners Donna and Greg closed up shop on their successful Rhode Island business and moved down to Virginia’s Eastern Shore to renovate the 1899 property which now houses the Fig Street Inn. Rates from $169.

Set Up Camp

Kiptopeke State Park, 3540 Kiptopeke Drive

The Kiptopeke State Park is an excellent option for large groups visiting the area. There are five 6-bedroom lodges complete with kitchen, bathrooms, linens, heat and air. Pets are permitted for an additional fee. In addition to these family lodges, the park has a yurt which can accommodate up to six people, and more than 140 campsites are available to book. Rentals from $83, $20 for campsites.

Look Out

Kings Creek Inn, 3018 Bowden Lane

The 1746 Colonial plantation home that houses Kings Creek Inn was completely renovated in 2000 and has been operating as a bed and breakfast since 2003. Located on 2.5 acres of land, the inn overlooks Kings Creek and the Chesapeake Bay. Kings Creek Inn offers 4 guest rooms and working fireplaces as well as on-site dining in the brick-clad salon. Rates $124 – $210.

Be Front and Center

The Oyster Farm, 500 Marina Village Circle

The Oyster Farm offers luxury waterfront villas and operates as part of the Kings Creek Marina and Resort. All rentals are within walking distance of the historic downtown area and just a short ride away from local golf courses. Rates $250 – $795.

Lounge Around

Bay Haven Inn, 403 Tazewell Avenue

The Bay Haven Inn’s large wrap-around porch is only the first of its enticements. Owners Jim and Tammy Holloway are known state-wide for their excellent innkeepers’ breakfast, including the very popular sweet potato biscuits. In addition to comfortable rooms, the 1906 Colonial-Revival home is surrounded by a lush garden, which in the spring and summer months is an absolute trove for bloom-lovers and hummingbird-watchers. Rates from $169.


Shack Up

The Shanty, 33 Marina Road

Located directly on the Cape Charles Harbor, The Shanty menu offers locally-sourced meals and fresh catch seafood daily. Be sure to try the steamed mussels, blackened fish tacos and bayshore burger, which is topped with an extra helping of cheddar and grilled chorizo. The covered deck and bar are a popular gathering spot and the restaurant often hosts live music.

Stay Awhile

Kelly’s Gingernut Pub, 133 Mason Avenue

Located in a restored 1907 bank building, Kelly’s Gingernut Pub has wide menu featuring everything from steaks and game to local seafood and basic barfare. Open for lunch, dinner and drinks year round, Kelly’s invites guests to sit down at the 100-year-old yellow pine bar and have a pint of Guinness.

Raise Your Spirits

DeadRise Pies, 425 Mason Avenue      

This community-oriented pizza shop is all about the dough—which is made from 100 percent non-GMO domestic wheat. In fact, all of the ingredients at DeadRise Pies (a name which derives from the Deadrise workboats so prevalent throughout the Chesapeake) are locally sourced and organic when possible.

Cool Off

Brown Dog Ice Cream, 203 Mason Avenue

Using only fresh and locally-sourced ingredients, this coastal creamery prides itself in producing unique flavor combinations in its so-called “test kitchen.” The winning results of these “secret recipes” include black raspberry, coconut almond crunch and avocado with strawberry. (Please note that Brown Dog Ice Cream is closed for the winter, but pints of your favorite flavor may still be purchased at Gull Hummock Gourmet Market.)

Park Yourself

Coach House Tavern, 1 Clubhouse Way

The Coach House Tavern at Bay Creek has beer on tap, five large screen televisions and a comfortable rustic ambiance. The menu also features regular lunch, brunch, and dinner options, including fish sourced from local waters.

Have a Sip

Chatham Winery offers tastings through December.

Photo by Keith Lanpher Photography

Chatham Vineyards and Winery, 9232 Chatham Road (Machipongo)

Chatham Farm has been a working farm for 400 years, and since 1999 . Currently owned and operated by the Wehner family, who are second-generation winegrowers on the property, Chatham Vineyards has been operating since 1999. The more than 20 acres of vines yield nearly 5,000 cases of Merlot, Cabernet Franc, Chardonnay and Provence-style Rosé each year. The winery offers tastings April – December. Closed Tuesday and Wednesday. $

Enjoy a Cuppa

Cape Charles Coffee House, 241 Mason Avenue

The building which houses the Cape Charles Coffee House was built in 1910 as a bank. After being damaged in a fire, the bank building later housed a fine clothing store. Now, you can find a charming and comfortable café on the first floor, with a menu of all the usual prepared drinks and a selection of artisan pastries, muffins, and cakes, including the decadent mascarpone custard cake. Upstairs, a gallery offers a look at the building’s art deco chandeliers and tin panel ceilings.


Trade Up

Machipongo Trading Company, 13037 Lankford Highway (Machipongo)

The Machipongo Trading Company began in 2008 as a retail outlet for the Eastern Shore Coastal Roasting Company’s tea and coffee. Today, there’s a bit more to it. The smallish shop has everything from art and gifts to breakfast, lunch, ice cream, tea and coffee. Machipongo has been voted best by the community for their supply of local goods in particular.

Take a Stroll

The Boardwalk, 316 Mason Avenue

The Boardwalk is a specialty shop full of unique regional gifts: jewelry, accessories and home wares run the gamet. Open since 2011, the boutique aims to delight customers with surprising souvenirs that will always remind them of time spent in Cape Charles.

Indulge Your Tastes

Gull Hummock Gourmet Market, 115 Mason Avenue

Named for a low-tide island on which waterfowl tend to perch and preen, the Gull Hummock Gourmet Market invites visitors to come in and stay awhile. The market stocks a wide variety of wine, beer, crackers, cheeses and other entertaining products and also hosts regular tastings of local artisanal food and wine on the weekends.

Leave Your Mark

Love Letters, 12 Strawberry Street

Love Letters is a specialty retail shop with gifts, clothing, and accessories that can be personalized at the in-house personalization bar. Closed Tuesdays.


Know Your History

Eastern Shore Historical Society, 69 Market Street, Onancock

The Eastern Shore Historical Society serves as an educational center for the Eastern Shore community. With numerous sites along the Heritage Trail, like Ker Place with its Georgian architecture and permanent displays of period furnishings, ESHS offers visitors a chance to dig deeper into the culture and history of the Eastern Shore.

Shoot the Breeze

Bay Creek Golf Courses, 3335 Stone Road

Bay Creek was the first resort to feature two signature 18-hole golf courses. The Arnold Palmer course is situated on the Chesapeake Bay and features manicured landscaping and large sand bunkers, while the Jack Nicklaus course offers views of Old Plantation Creek and pairs the landscape with natural dunes.

June 11, 2022

Star Gazing and Laser Nights

Virginia Living Museum
July 9, 2022

Star Gazing and Laser Nights

Virginia Living Museum
August 13, 2022

Star Gazing and Laser Nights

Virginia Living Museum