Discover Virginia's Oyster Trail: 7-Day Itinerary

Oyster Tasting, Virginia Beach, Virginia, water, seafood, beach, USA
Enjoy an oyster farm tour and tasting in Virginia Beach (Photo courtesy Virginia Tourism Corporation)
Visit Merroir, the waterfront tasting room of Rappahannock Oyster Company
The 20-mile-long Chesapeake Bay Bridge Tunnel
oysters, roast, event, Reedville, Virginia, museum, seafood, festival, USA
Reedville Fishermen's Museum annual oyster roast
Tangier Island
Oyster Tasting, Virginia Beach, Virginia, water, seafood, beach, USA
oysters, roast, event, Reedville, Virginia, museum, seafood, festival, USA

Virginia is the largest producer of fresh, farm-raised oysters on the East Coast of the US. Here, the Chesapeake Bay (the largest estuary in the US) and its tributaries provide a mix of saltwater and fresh, creating different flavours among Virginia oysters. Virginia oysters thrive in eight regions and visitors can experience a taste of each along the Virginia Oyster Trail. 

Covering coastal and tidewater Virginia, the trail highlights restaurants, seafood companies, oyster farms and tours where visitors can experience Virginia oyster culture, sampling different varieties of oysters along the way. This itinerary provides an in-depth exploration of Virginia’s Oyster Trail. Most regions are located within an hour’s drive of each other, so the tour can be shortened to include highlights from each region for visitors with less time. 

Day 1: Upper Bay Western Shore Region

Fly into Washington Dulles International Airport and then travel by car to Stratford, Virginia (2.5 hours).  Spend the night at the Inn at Stratford Hall and tour the historic home of General Robert E. Lee. Travel to nearby Colonial Beach for a meal at Denson’s Grocery and R&B Oyster Bar. Learn more about the waterman culture at the Fishermen’s Museum in Reedville which also hosts an annual oyster roast in November. 

Day 2: Middle Bay Western Shore

Follow the Rappahannock River south to the Tides Inn in Irvington (1.25 hours). This waterfront resort is located where the Chesapeake Bay Wine Trail meets the Virginia Oyster Trail, offering visitors numerous culinary excursions. The Dog and Oyster Vineyard features Virginia wines crafted to complement the local oysters available at the winery every weekend courtesy of Byrd’s Seafood Company. Visit Merroir, the tasting room of Rappahannock Oyster Company in Topping for a waterfront meal from Virginia’s oyster experts. Book a Virginia Watermen Heritage Tour to get a firsthand look at the local watermen culture while exploring the bay.

Day 3: Lower Bay Western Shore

This region includes the historic locations of Williamsburg and Yorktown. Travel to the Williamsburg Winery (1.25 hours) which features not only a winery but a tavern, restaurant, and lodging at The Wedmore Place. The winery’s Gabriel Archer Tavern hosts a Wine & Brine Lounge every Saturday and Sunday, featuring Virginia oysters and seafood. Tour the Watermen’s Heritage Museum in nearby Yorktown.

Day 4: Tidewater

Travel an hour south to Virginia Beach, the state’s premier beach destination. Located right on the beach, The Oceanfront Inn offers packaged experiences highlighting the local culture. Pleasure House Oysters hosts boat-based farm and tasting tours along the Lynnhaven River. The “Chef’s Table Tour” is a unique dining experience featuring local foods served at a table on the farm or on the boat. Taste Tidewater Tours offers a Virginia Wine and Oyster Tour and a Local Oyster and Craft Brew Tour, where guests sample oyster-based dishes from Virginia Beach restaurants paired with local wines and beers.  

Day 5: Lower Bay Eastern Shore, Upper Bay Eastern Shore and Seaside

No visit to Coastal Virginia is complete without a trip across the Chesapeake Bay Bridge Tunnel, a four-lane 20-mile-long vehicular toll crossing the lower Chesapeake Bay. The tunnel connects the 70-mile long Eastern Shore to the mainland. The Eastern Shore is home to three regions of the Virginia Oyster Trail. Spend two nights at the centrally located Inn at Onancock (1.5 hours from Virginia Beach). From here, explore quaint fishing villages including Chincoteague Island, home to the famous Chincoteague ponies that live in the Chincoteague National Wildlife Refuge. Schedule a visit during the town’s annual oyster festival in October. 

Day 6: Tangier/Middle Chesapeake Bay

Your final stop along Virginia’s Oyster Trail takes you to the newest region to be added to the trail and one of the most unique destinations in Virginia. Tangier Island is located 12 miles out in the Chesapeake Bay and is only accessible by air or sea. The Tangier Onancock Ferry departs runs twice daily from May to October and private charters are also available. Once on the island, explore the narrow streets travelled mostly by bicycle or golf cart and enjoy the warm hospitality of the island’s residents. Enjoy a meal at Lorraine’s, home to the Tangier Island Oyster Company. 

Day 7: Return

The drive time from Onancock to Washington Dulles International Airport is four hours. Traveling north along the Eastern Shore into Maryland and around Washington, DC, this scenic route provides numerous opportunities to continue exploring the Capital Region. 

Related: 
Scenic Drives
Outdoors & Nature
Tours & Trails
Wine & Cuisine
City Adventures
History & Culture