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 (777) June (463) July (361) August (243) September (142) October (86) November (58) December (83) January (11) February (8) March (9) April (9) Cities Chestertown (97) Crisfield (7) (-) Easton (3) (-) Galena (1) Rock Hall (4) Salisbury (4) (-) St. Michaels (284) Regions Eastern Shore (288) Types Fairs & Festivals (34) Food & Drink (287) History & Heritage (180) Nature & Outdoor (255) Ongoing (101) Performing Arts (4) Sports (1) 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 3-November 22, 2025 St. Michaels Farmers Market St. Michaels Learn More May 3-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More May 4-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More May 5-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More May 6-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More May 7-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More May 8-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More May 9-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More May 10-November 22, 2025 St. Michaels Farmers Market St. Michaels Learn More May 10, 2025 Annual Galena Dogwood Festival Galena Learn More May 10, 2025 C3 Tri-County Ice Cream Classic Easton Learn More May 10-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More Pagination First previous Current page 1 Page 2 Page 3 Page 4 Page 5 Page 6 Page 7 Page 8 Page 9 … Next Last
