Chesapeake Country Scenic Byway Events Plan your road trip on our Byways to visit during local special events and enjoy an authentic Maryland experience. Filter Results: February (262) March (465) April (332) May (341) June (280) July (234) August (236) September (202) October (241) November (118) December (62) January (1) Cities (-) Chestertown (2) Church Creek (1) Crisfield (1) Easton (6) Rock Hall (1) Regions Eastern Shore (2) Types Fairs & Festivals (5) Food & Drink (910) History & Heritage (46) Nature & Outdoor (865) Ongoing (862) (-) Performing Arts (2) Visual Arts (65) Narrow Your Event Search Start Date End Date Search By Keyword Quick Search This Week Next Week This Month Next Month Reset Applied Filters April 25-26, 2026 Paint The Town Show + Sale Chestertown Learn More April 26, 2026 Paint The Town Show + Sale Chestertown Learn More
