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: January (174) February (329) March (216) April (150) May (176) June (167) July (140) August (145) September (122) October (158) November (77) December (48) Cities Chestertown (54) Crisfield (4) St. Michaels (430) Regions Eastern Shore (488) Types Fairs & Festivals (4) (-) Food & Drink (488) History & Heritage (62) Multicultural (9) Nature & Outdoor (430) Ongoing (432) Performing Arts (2) Visual Arts (59) Narrow Your Event Search Start Date End Date Search By Keyword Quick Search This Week Next Week This Month Next Month Reset Applied Filters June 19-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 19-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 20, 2026-January 2, 2027 Chestertown Farmers Market Chestertown Learn More June 20-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 20-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 21-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 21-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 22-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 22-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 23-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 23-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 24-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More Pagination First Previous … Page 10 Page 11 Page 12 Page 13 Current page 14 Page 15 Page 16 Page 17 Page 18 … Next Last
