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 (142) March (469) April (338) May (342) June (280) July (234) August (236) September (202) October (241) November (118) December (63) January (1) Cities Chestertown (48) Crisfield (4) Easton (5) St. Michaels (860) Regions Eastern Shore (917) Types (-) Civil War (5) Fairs & Festivals (10) (-) Food & Drink (912) History & Heritage (52) Miscellaneous (2) Nature & Outdoor (868) Ongoing (861) Performing Arts (11) Visual Arts (62) 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 23-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More April 23-November 15, 2026 Beer Tasting Cruises on Epiphany! St. Michaels Learn More April 23-November 15, 2026 Half-Day Private Sail 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 24-November 15, 2026 Beer Tasting Cruises on Epiphany! St. Michaels Learn More April 24-November 15, 2026 Half-Day Private Sail on Epiphany! St. Michaels Learn More April 25, 2026-January 2, 2027 Chestertown Farmers Market Chestertown 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 April 25-November 15, 2026 Beer Tasting Cruises on Epiphany! St. Michaels Learn More April 25-November 15, 2026 Half-Day Private Sail 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
