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: February (356) March (241) April (169) May (187) June (192) July (149) August (150) September (125) October (160) November (77) December (48) January (1) Cities Chestertown (2) (-) St. Michaels (430) Regions Eastern Shore (430) Types Food & Drink (430) Nature & Outdoor (430) (-) Ongoing (430) 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 9-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 9-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 10-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 10-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 11-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 11-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More 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 Pagination First Previous Page 1 Page 2 Page 3 Page 4 Current page 5 Page 6 Page 7 Page 8 Page 9 … Next Last
