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 (63) February (375) March (236) April (166) May (179) June (171) July (146) August (150) September (124) October (159) November (77) December (48) Cities Chestertown (52) Crisfield (4) St. Michaels (430) Regions Eastern Shore (486) Types Fairs & Festivals (4) (-) Food & Drink (486) History & Heritage (59) Miscellaneous (3) Multicultural (2) Nature & Outdoor (432) Ongoing (432) Performing Arts (3) Visual Arts (51) 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 12-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 12-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 13-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 13-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 14-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 14-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 15-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 15-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 16, 2026-January 2, 2027 Chestertown Farmers Market Chestertown Learn More May 16-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 16-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 17-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More Pagination First Previous … Page 3 Page 4 Page 5 Page 6 Current page 7 Page 8 Page 9 Page 10 Page 11 … Next Last
