Your Guide to Chesapeake Bay Festivals

Sixteen music, art, and food festivals you don't want to miss this summer.

Fewer crabs, higher prices, not great! Photograph by Jay Fleming.

Country Life Festival

July 1-3

Chainsaw carving, air rifle shooting, watermelon-eating contests, and other diversions you won’t find at a typical DC street festival. 42455 Fairgrounds Rd., Leonardtown, Md.; 301-399-8523.


July 9

At the Calvert Marine Museum, attendees can see live sharks, craft a shark hat, pose for a picture in the jaws of a Megalodon shark, and have other fin fun. 14200 Solomons Island Rd., Solomons, Md.; 410-326-2042.

Potomac Jazz & Seafood Festival

July 9

This year’s lineup of jazz artists includes Selina Albright, Matt Marshak, and Eric Darius. 38370 Point Breeze Rd., Coltons Point, Md.; 301-769-2222.

Easton's Plein Air festival. Photograph by Mark Sandlin.
Easton’s Plein Air art festival. Photograph by Mark Sandlin.

Plein Air Easton

July 9-17

Dozens of artists fill the streets at the country’s largest outdoor painting competition. Downtown Easton, Md.; 410-822-0345.

Berlin Bathtub Races

July 15

As wacky as it sounds. Main Street, Berlin, Md.; 410-641-4775.

J. Millard Tawes Crab and Clam Bake

July 20

The festival, now in its 40th year, attracts seafood lovers as well as Maryland politicans out to shake palms stained with Old Bay. Admission: $45 and up. Somers Cove Marina, 715 Broadway, Crisfield, Md.; 410-968-2500.

Chincoteague ponies during the annual pony penning and swim from Assateague. Photograph by Bonnie U. Gruenberg/<a href="">Wikimedia Commons</a>.
Chincoteague ponies during the annual pony penning and swim from Assateague. Photograph by Bonnie U. Gruenberg/Wikimedia Commons.

91st Annual Chincoteague Pony Swim

July 27

A team of “saltwater cowboys” leads a herd of wild ponies across the channel from Assateague Island to Chincoteague Island, where they’re auctioned off the next day. Memorial Park, 7427 Memorial Park Dr., Chincoteague Island, Va.

Tidewater Archaeology Days

July 30-31

Tour the excavations and the archaeology lab at this colonial site. Historic St. Mary’s City, 18559 Hogaboom Lane, 240-895-4990.

12th Annual Oyster Buy Boat Reunion and Shuck-N-Suck

August 4-7

See boats that are part of the Chesapeake’s heritage, and eat oysters every which way—raw, roasted, fried, and more. Oyster Farm Marina at Kings Creek, Cape Charles, Va., 757-331-8640.

Rotary Club of Annapolis Crab Feast

August 5

The world’s largest crab feast, now in its 71st year, attracts nearly 2,500 people who devour about 350 bushels of crabs, 3,400 ears of corn, and hundreds of gallons of beer. Adult admission: $65 and up. Navy-Marine Corps Memorial Stadium, Annapolis, 877-333-9667.

The Great Chesapeake Balloon & Wine Festival

August 5-6

Ride a hot air balloon ($225) or just see them all lit up at night. Triple Creek Winery, 11138 Three Bridge Branch Rd., Easton, Md., 410-924-4190.

St. Mary’s County National Lawn Mower Races

August 5-6

If Berlin can race bathtubs, why not lawn mowers down on a farm? 22880 Budd’s Creek Rd., Clements, Md., 301-475-2139.

Governor’s Cup Yacht Race

August 5-6

This annual event, now in its 44th year, is an overnight race on the Chesapeake—from Annapolis, the Maryland capital, to the state’s first capital, St. Mary’s City. Email for more information.

L’il Margaret’s Bluegrass & Old Time Music Festival

August 11-13

On the schedule: 27 hours of live country music, including The Hillbilly Gypsies, Little Roy Lewis and Lizzy Long, and Kody Norris and the Watauga Mountain Boys. 20529 White Point Rd., Leonardtown, Md., 301-475-8191.

Photograph courtesy of Rock Hall's Pirates and Wenches Weekend.
Photograph courtesy of Rock Hall’s Pirates and Wenches Weekend.

Rock Hall’s Pirates and Wenches Weekend

August 12-14

Rum tastings, live music, sea-chantey sing-alongs, a pirate encampment, and decorated dinghies fill a wild weekend in Rock Hall. Rock Hall, Md.

Watermen’s Appreciation Day & Crab Feast

August 14

This Chesapeake Bay Maritime Museum event includes a “watermen’s rodeo” boat-docking contest, live music, games for kids, and bushels of steamed crabs. 213 N. Talbot St., St. Michaels, Md., 410-745-2916.

This article appears in our July 2016 issue of Washingtonian.