Things to Do In Onancock VA and Tangier Island on The Chesapeake

WHY GO: Onancock VA, on the southern end of the Delmarva Peninsula, and the working man’s Tangier Island in the Chesapeake Bay have never been on any “hotspot” list. Life in these parts revolves around the water: oysters, crabs, duck-hunting, millions of migratory birds.

But all this peace and quiet does have its advantages as a romantic getaway. The Eastern Shore of Virginia is a mere 5 hours drive from New York City (as long as it takes to get to Lake Placid), and attractions, food and lodging are surprisingly sophisticated.  Where else can you kayak to an award-winning vineyard for a wine and cheese tasting afternoon?

To extend your Getaway, combine with this visit to Chincoteague and this one to Cape Charles VA at the tip of the Delmarva Peninsula.

Onancock is on our list of 20 Surprisingly Romantic Getaways in VA. Check it out if you wish to explore the state further.

Looking for someplace dreamy outside of Virginia? Check out our 150 Best Romantic Getaways in the Northeast US (Virginia to Maine).

Things to Do in and around Onancock VA on the Eastern Shore

DO: Kayak To Chatham Vineyards for Wine Tasting on the “Paddle Your Glass Off” Tour

No big surprise that kayaking Chesapeake Bay, especially on a kayaking-wine tasting tour to Chatham Vineyards, is one of the most popular activities on the Eastern Shore. Paddle from a tiny bayside village of Bayford (Southeast Expeditions provides directions), around a spectacular cove, walk about ½ mile past an 1818 Federal red brick Manor House to taste some award-winning wine, and leave with a bottle of said wine per couple.  What’s not to like?

Winery owner Jon Wehner grew up on his parent’s vineyard in Northern Virginia.  He and his wife, Mills, established Chatham Vineyards in 1999 on twenty acres of Eastern Shore. With its moderate maritime weather, and sandy loam soils it was the perfect region to grow Chardonnay, Merlot, Cabernet Franc, Cabernet Sauvignon and Petit Verdot grapes.

“This isn’t a big party place – we’re serious wine maker – the real deal,” says Wehner, who buys his oak casks from France. Wine Enthusiast Magazine has named Chatham’s Steel Chardonnay (fermented in stainless steel vats) as one of the top 100 Chardonnay’s in the country. “You can taste this place,” Jon admits.  Check website for tour dates and prices.

TOUR: Tangier Island, from Onancock

At 1.2 square miles (and disappearing fast) Tangier Island, is one of the last authentic fishing villages in the Chesapeake Bay, and where many of the 400 or so residents still speak with an Elizabethan dialect. It is 12 miles – and a world away – from the mainland.

Though there are no banks (or ATM’s), no jails or hospitals, Tangier Island does have its own mayor. And though it welcomes tourists, the island has its own insular, quirky ways. You might have lived on Tangier for decades, but if you weren’t born and raised here, you’re forever a “come-‘ere.”

Take the ferry from Onancock (Joyce Marie II, $30 roundtrip)  and pay attention as you pull into harbor – you’ll pass bungalows on stilts where Eastern Shore watermen haul their catch, and small crabbing boats plying the waters.

Tour Tangier

Golf carts are the accepted mode of transport here, and you can get a quick ten minute tour of the island (that’s all it takes!) given by lively residents. Stop into the Tangier History Museum for a quick overview of life here, and be sure to make some purchases at women-owned gift shops, like  Sandy’s Place.

Go on a Crab Shanty or Waterman tour to find out where your evening’s soft-shell crab dinner comes from then grab a creamy, delicious Queen Crab Soup, and a Crab Cake at Lorraine’s. 

VISIT: Ker Place, Onancock

Built in 1799, and the only fully intact Greek Revival Federal-era home on the eastern shore, Ker Place is considered the “Crown Jewel of the Peninsula” by many historical preservationists. John and Agnes Ker (pronounced “car”) received this home and 675 acres as a wedding gift.

Astoundingly, all window glass panes and moldings are original to the house. Most of the furniture, including the couple’s carved four-poster trundle bed, is as well. Mauve parlor walls, and cantaloupe-yellow painted bedrooms are indicative of the bold use of color at the time.

John died of Mercury poisoning in his 30’s (he was taking medication laden with it). So Agnes, in her grief, had black stripes added to green moldings throughout the house.

Don’t leave before inspecting a small portrait of George Washington, painted by Gilbert Stuart and his daughter, Jane, who helped him complete many of his portraits. Both Gilbert and Jane’s name grace the frame, a rare find indeed. Check website for tour dates, hours, and fees.

VISIT: Barrier Islands Center, Route 13 between Onancock and Cape Charles

A map of the Eastern Shore at the engaging Barrier Islands Center shows a string of barrier islands off the Atlantic Coast. Known as “Nature’s Speed bumps” – because they mitigate hazardous swells created by Atlantic Ocean storms – some of these spits of land, such as Hog Island and Cobb’s Island, once featured popular resorts, Gun Clubs, seafood companies, and self-sufficient full-time residents.

But after major storms in 1933 destroyed homes and endangered lives, islanders gave up this way of life. They actually floated whole houses off the island and onto the Eastern Shore, where they were relatively safe.

In the 1970’s, out-of-town and out-of-state collectors were buying anything and everything that came off those barrier islands. The Barrier Island Center was established to preserve and keep these artifacts where they belong: for example, remnants from Cobb’s Island Hotel. This fine establishment catered to wealthy hunters who arrived with personal hunting guides.

There’s also  a whole section on duck decoys fashioned by famous carvers. The antique farmhouse in which the museum is housed features a rare 1890’s “twisted chimney” in the attic. To learn more about this vanished way of life, watch the Barrier Island Center documentary, “Our Island Home,” shown on PBS.

SHOP: Red Queen Gallery, Onancock

Contemporary paintings, arts and crafts, photography, antique sea glass, old Coke bottle pencil holders, pottery, sculpture, functional art made from golf clubs – it’s a mix of delights for thinking people.  “We’re lucky we have a wealth of people here,” says the owner. And she wasn’t talking net worth.

SHOP: Crocket Gallery, Onancock

Local landscape artist, Willie Crocket, talks to you as he paints. His oils start at reasonable amounts, and includes frames! In fact, the photo above, of a spectacular Onancock sunrise, is a Willie Crocket original.

SHOP: Market St. Antiques, Onancock

This is the go-to place for antiques and architectural salvage, plus some local “flavor.” Pick up a can of Blue Crab Bay Co. flavored nuts – a welcome souvineer of the area for so many.

SHOP: Main Street Onancock

More shops to peruse include Dawn and Marker 29 for women’s clothing and accessories; Fable Made, Morphosis Gallery and Imaginarium for cool and unusual gifts, and more antique and restoration stores.

 Where to Eat in Onancock VA and the Eastern Shore

EAT: Mallard’s At the Wharf

In its prior life, this was Hopkin’s Bros. General Store. It’s now home to “musical chef” Johny Mo. Nosh on local oysters, salads, wings and wraps on the outdoor deck hard by a dock where boats practically nod up onto your lap.

EAT: Locals also recommend

Onancock Taphouse for craft beer on tap. Market St. Grill for traditional American. Maurice for French/Thai fusion. The Charlotte Hotel Restaurant for innovative fare. and Bizzotto’s Gallery Cafe for seafood. Blarney Stone Pub, for fish and chips.

Best Places to Stay in Onancock Virginia

STAY: Inn at Onancock

In November 2016, new owners Kim Moore and Matt Spuck purchased Inn at Onancock from Lisa and Kris LaMontagne. Opulent, eclectically decorated rooms will not disappoint the most jaded traveler. Stone floor soaking-tub bathrooms are of a “let me ease back and unwind” caliber.

Breakfast includes a locally roasted private blend of coffee, fresh buttermilk biscuits, Greek yogurt with locally sourced fruits, home made granola, frittata made from local eggs (Shine and Rise Farm) and other delicacies you’d expect from a Select Registry property. 

STAY: Charlotte Hotel and Restaurant, Onancock

An old-world in-town hotel with a modern twist, The Charlotte Hotel is an intimate boutique hotel. Charlotte is also known for it’s terrific restaurant.

STAY: Several other Worthy Bed and Breakfasts

Both the 1882 Colonial Manor Inn, and Spinning Wheel B&B and ooze Onancock hospitality.