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 (321) March (212) April (149) May (176) June (167) July (140) August (145) September (119) October (158) November (77) December (48) Cities Chestertown (2) St. Michaels (430) Regions Eastern Shore (432) Types Fairs & Festivals (1) Food & Drink (484) History & Heritage (59) 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 April 20-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More April 20-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More April 21-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More April 21-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More April 22-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More April 22-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More April 23-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More April 23-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More April 24-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More April 24-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More April 25-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More April 25-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More Pagination First Previous Page 1 Current page 2 Page 3 Page 4 Page 5 Page 6 Page 7 Page 8 Page 9 … Next Last
