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 (188) February (321) March (212) April (149) May (176) June (167) July (140) August (145) September (119) October (158) November (77) December (48) Cities Chestertown (54) Crisfield (1) Salisbury (10) St. Michaels (430) Regions Eastern Shore (495) Types Fairs & Festivals (1) Food & Drink (484) History & Heritage (60) Multicultural (10) Nature & Outdoor (430) Ongoing (432) Performing Arts (2) Visual Arts (60) 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 29-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 29-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 30, 2026-January 2, 2027 Chestertown Farmers Market Chestertown Learn More May 30-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 30-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 31-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 31-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 1-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 1-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 2-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 2-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 3-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More Pagination First Previous … Page 7 Page 8 Page 9 Page 10 Current page 11 Page 12 Page 13 Page 14 Page 15 … Next Last
