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 (94) 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 (2) St. Michaels (860) Regions Eastern Shore (914) Types (-) Civil War (2) Fairs & Festivals (10) (-) Food & Drink (912) History & Heritage (52) Miscellaneous (2) Nature & Outdoor (868) Ongoing (861) Performing Arts (8) 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 June 26-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 26-November 15, 2026 Beer Tasting Cruises on Epiphany! St. Michaels Learn More June 26-November 15, 2026 Half-Day Private Sail on Epiphany! St. Michaels Learn More June 27, 2026-January 2, 2027 Chestertown Farmers Market Chestertown Learn More June 27-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 27-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 27-November 15, 2026 Beer Tasting Cruises on Epiphany! St. Michaels Learn More June 27-November 15, 2026 Half-Day Private Sail on Epiphany! St. Michaels Learn More June 28-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More June 28-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More June 28-November 15, 2026 Beer Tasting Cruises on Epiphany! St. Michaels Learn More June 28-November 15, 2026 Half-Day Private Sail on Epiphany! St. Michaels Learn More Pagination First Previous … Page 23 Page 24 Page 25 Page 26 Current page 27 Page 28 Page 29 Page 30 Page 31 … Next Last
