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 (466) April (335) May (342) June (280) July (234) August (236) September (202) October (241) November (118) December (63) January (1) Cities Cecilton (1) Chesapeake City (1) (-) Chestertown (69) Church Creek (3) Crisfield (4) (-) Easton (9) (-) Rock Hall (1) St. Michaels (860) Regions Eastern Shore (78) Western Maryland (1) Types Civil War (5) Fairs & Festivals (6) Food & Drink (50) History & Heritage (49) Miscellaneous (1) Multicultural (1) Nature & Outdoor (7) Ongoing (2) Performing Arts (10) Visual Arts (66) Narrow Your Event Search Start Date End Date Search By Keyword Quick Search This Week Next Week This Month Next Month Reset Applied Filters February 20-28, 2026 The Prompted Image: A Challenge To Artists Chestertown Learn More February 21, 2026-January 2, 2027 Chestertown Farmers Market Chestertown Learn More February 21-28, 2026 The Prompted Image: A Challenge To Artists Chestertown Learn More February 21, 2026 Native American Heritage & Artifact Day Easton Learn More February 22-March 29, 2026 Elegant Afternoon Tea at Brampton 1860 Chestertown Learn More February 22, 2026 A Cozy Winter Concert of Classical Music Rock Hall Learn More February 22-28, 2026 The Prompted Image: A Challenge To Artists Chestertown Learn More February 23-28, 2026 The Prompted Image: A Challenge To Artists Chestertown Learn More February 23-27, 2026 Uncle Nace: The Day Freedom Came One Man Performance Easton Learn More February 24-28, 2026 The Prompted Image: A Challenge To Artists Chestertown Learn More February 24-27, 2026 Uncle Nace: The Day Freedom Came One Man Performance Easton Learn More February 25-28, 2026 The Prompted Image: A Challenge To Artists Chestertown Learn More Pagination First previous Current page 1 Page 2 Page 3 Page 4 Page 5 Page 6 Page 7 Next Last
