Home to wildlife, wineries, oysters and history, this 200-mile-long estuary along the coasts of Maryland and Virginia—the largest in North America—boasts plenty to do on the water and along its wild shoreline. Put these 15 favorites at the top of your next Chesapeake itinerary.
Photo: Tim Horvath
The Thomas Point Shoal Lighthouse looks more like a quaint cottage lost in the middle of the Bay, which might be why it’s one of the most photographed lighthouses in America. The hexagonal structure was built in 1875 one-and-a-half miles from shore; now, a consortium of the Chesapeake Chapter of the U.S. Lighthouse Society, the City of Annapolis, Anne Arundel County, and the Annapolis Maritime Museum, manages and preserves this beloved National Historic Landmark. The museum offers docent-led tours several months of the year, including a 30-minute boat ride to and from the lighthouse.
Photo: Courtesy of Annapolis Sailing School
In a city that dubs itself “America’s Sailing Capital,” what better way to spend a day than learning the ropes of a classic Chesapeake Bay pastime? The Annapolis Sailing School offers 2-hour “TrySail” courses for novice watermen (and women) looking for a hands-on crash course in captaining a sailboat. Following the lesson, pop into Middleton Tavern, an Annapolis mainstay known for its crab cakes and oyster shooters.
Photo: James Trudeau
Fly over rivers, trees, farmland, and shorelines while taking in stunning 360-degree views of the Chesapeake Bay aboard a hot-air balloon. Delmarva Balloon Rides in Chester, Maryland, offers year-round rides. Or, witness a spectacle in the sky at the annual Chesapeake Bay Balloon and Wine Festival in August, where up to 15 hot air balloons float in tandem in Easton, Maryland.
Photo: Paula Jasinski
The Chesapeake Bay is rife with aquatic delicacies—oysters and blue crabs, especially—but exactly how do they get from Bay to plate? Watermen Heritage Tours connects you with commercial fishermen, crabbers, and oystermen who will give you an insider’s look at things like oyster tonging, crab shedding, and aquafarming in customized trips. Bonus points for the scenery you’ll encounter (think lighthouses and nature preserves) along the way.
Photo: Courtesy of Jamestown-Yorktown Foundation
At the mouth of the York River, which empties into the Chesapeake in Virginia, Yorktown's brand-new American Revolution Museum tells the story of America’s fight for independence through interactive exhibits, artifacts, and films in the city where it all happened. Down the street, the Watermen’s Museum documents the Chesapeake’s seafaring history, including an exhibit dedicated to Captain John Smith’s inaugural trek up the bay more than 400 years ago.
Photo: Courtesy of Bay Creek Resort & Club
No choice is a bad one at the Bay Creek Resort & Club, where you can tee off at one of two signature courses designed by Jack Nicklaus and Arnold Palmer. The award-winning golf resort boasts breathtaking views of the Chesapeake Bay and Old Plantation Creek, miles of walking and biking trails, and a casual tavern to kick back with an icy brew post-game.
Photo: Virginia State Parks
The Delmarva Peninsula—which encompasses the parts of Virginia and Maryland that separate the Chesapeake from the Atlantic—is a highway for more than 400 bird species, thanks to its wetlands, swamps, forests, and fields. Bird watchers gather several times a year to scout the skies in places like Kiptopeke State Park, one of many stops along the way in the Eastern Shore Birding and Wildlife Festival.
Photo: Courtesy of Chesapeake Bay Maritime Museum
The Chesapeake Bay Maritime Museum in St. Michaels, Maryland, maintains the largest collection of historic Chesapeake Bay watercraft, from skiffs and skipjacks to old crabbing vessels. In the museum’s working boatyard, you can witness restoration of historic wooden boats in action. Or, if you’re up for it, sign up to apprentice with a shipwright to learn the trade hands-on. The 18-acre waterfront museum also features a historic lighthouse, butterfly garden, living shoreline, and exhibits highlighting the Bay’s history.
Photo: Courtesy of Dog & Oyster Vineyard
Spend a day exploring the Chesapeake Bay Wine Trail, which features nine wineries mostly along the middle peninsula of Virginia. Jacey Vineyards offers dock access for water-bound travelers, and The Dog and Oyster Vineyard crafts wines specifically suited to oyster pairings. Visit the trail during the spring and fall oyster crawls, where each participating winery whips up a unique local oyster dish to serve with their wine.
Yes, this is a thing. This half-day tour from SouthEast Expeditions in Cape Charles, Virginia, takes you on a 45-minute paddle through marshy creeks (a bird-watcher’s paradise) before dropping you on the banks of Chatham Vineyards, where you’ll score a tasting and a bottle of wine (included in the tour). Just remember: You do have to paddle back.
Photo: Courtesy of Maryland Department of Natural Resources
Once submerged beneath a shallow sea, the rugged shoreline at Calvert Cliffs State Park in Maryland is now a treasure chest of prehistoric gems. More than 600 species of fossils from the Miocene era (10 to 20 million years ago) have been discovered here, with ancient oyster shells and sharks’ teeth being the most common finds.
Photo: @fireflourfork via Instagram
With the Chesapeake Bay’s long history of working watermen, it’s no surprise the shores of the Bay are a jewel box of coastal souvenirs, from vintage fishing lures and buoys to artwork made from discarded oyster shells. The Blue Crow Antique Mall in Keller, Virginia, is home to roughly 200 antiques and crafts dealers, and on the opposite side of the Bay in Kilmarnock, Virginia, Kilmarnock Antique Gallery houses the largest collection of vintage oyster plates in the country.
Photo: Courtesy of the Chesapeake Bay Environmental Center
See the Bay and its untouched beauty at the Chesapeake Bay Environmental Center in Grasonville, Maryland. The 510-acre preserve is home to native woodlands, tidal marshes, meadows, and a plethora of wildlife, from otter and stingrays to terrapin turtles and more than 200 species of birds. Hop on a guided kayak tour where a certified naturalist will lead you on a narrated exploration through a marshy creek.
Photo: Scott Hardaway/VIMS
Score an insider’s look at the science that goes into understanding—and improving—the Bay and its wildlife at the Virginia Institute of Marine Science, the largest marine science laboratory in the U.S. focused on coastal and estuarine science. The Gloucester, Virginia, campus includes an oyster hatchery, one-acre teaching marsh, a seawater research laboratory, and a preserved fisheries collection with over 128,000 species collected from the Chesapeake Bay and around the world. The institute offers free behind-the-scenes tours with marine scientists in the summer, or by appointment year-round.
Photo: Courtesy of The Avalon Foundation
Small-town Easton, Maryland, is becoming increasingly known for its budding arts and culture scene. The Academy Art Museum, partially housed in an early 19th-century schoolhouse, features a permanent and rotating collection of local and national artists. Nearby, the Avalon Theatre, an impressive Art-Deco-style venue once dubbed the “Showplace of the Eastern Shore,” hosts a variety of performances, from comedians and orchestras to local and national musical acts.