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 St. Michaels (430) Regions Eastern Shore (430) 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 June 8-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 8-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 9-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 9-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 10-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 10-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 11-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 11-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 12-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 12-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 13-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 13-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More Pagination First Previous … Page 6 Page 7 Page 8 Page 9 Current page 10 Page 11 Page 12 Page 13 Page 14 … Next Last
