Chesapeake County Maryland Eastern Shore Chesapeake Bay Maryland Scenic Highwqy
Chesapeake Country National Scenic Byway

Whether you are on your way to the beach or just taking a drive to admire the beautiful Bay, the Chesapeake Wine Trail will lead you through one of the most scenic and charming parts of the state. East of the Chesapeake Bay, Maryland’s Eastern Shore is abundant with seafood, beaches, wildlife and history, and now a beautiful—and delicious—wine trail.

Click here for more Wine Trail information.

Chesapeake BAy BRidge
Discover the Arts
Along the Byway!
"Wine and Dine for Art Tour" Thursday, March 14th, 6:30 PM. Chesapeake City. Multi-course dinner featuring wine pairing and lectures or presentations by local Cecil County artists. For more information, visit or Call (410) 392-5740. For more information, call (410) 920-7018.

"Eastern Shore Wind Ensemble - Band Concert." Chestertown. Sunday, March 16, 4PM. This free-admission program will appeal to listeners of all ages. The ESWE is an all-ages community concert band based in Chestertown directed by Dr. Keith Wharton. For more information, please call (410)778-2829.

"The David Schiff Trio Spontaneous Invention." Saturday, March 22,7:00PM. Centreville. For more information, call (410) 758-2520,or visit

Maryland’s first nationally
designated scenic byway
Working landscapes and waterfronts
Historic town centers
Pristine natural areas
Historic main streets
Fish from a nearby pier
Hike - Bike - Paddle
Beauty - Tranquility
History - Traditions



Cecil County

Kent County

Queen Annes County

Chesapeake Bay Gateways Network

War of 1812

Funded in part by the Federal Highway Administration,
Cecil County, Kent County, and Queen Anne’s County

Chesapeake Byway Wine Trail Brochure