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: May (853) June (681) July (503) August (349) September (212) October (112) November (61) December (84) January (11) February (8) March (9) April (12) Cities Chestertown (98) Crisfield (7) Easton (3) (-) Galena (1) (-) Rock Hall (6) Salisbury (4) St. Michaels (283) Regions Eastern Shore (7) Types Fairs & Festivals (4) Food & Drink (4) Performing Arts (7) Visual Arts (1) Narrow Your Event Search Start Date End Date Search By Keyword Quick Search This Week Next Week This Month Next Month Reset Applied Filters May 10, 2025 Annual Galena Dogwood Festival Galena Learn More May 10, 2025 Vance Gilbert at The Mainstay Rock Hall Learn More May 17, 2025 Don Vappie at The Mainstay Rock Hall Learn More August 8-10, 2025 Pirates and Wenches Weekend Rock Hall Rock Hall Learn More August 9-10, 2025 Pirates and Wenches Weekend Rock Hall Rock Hall Learn More August 10, 2025 Pirates and Wenches Weekend Rock Hall Rock Hall Learn More October 11, 2025 Rock Hall FallFest Rock Hall Learn More