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 (164) February (360) March (219) April (150) May (176) June (167) July (140) August (145) September (122) October (158) November (77) December (48) Cities Chestertown (53) Crisfield (4) St. Michaels (430) Regions Eastern Shore (487) Types Fairs & Festivals (4) (-) Food & Drink (487) History & Heritage (63) Multicultural (8) Nature & Outdoor (432) Ongoing (432) Performing Arts (3) Visual Arts (58) Narrow Your Event Search Start Date End Date Search By Keyword Quick Search This Week Next Week This Month Next Month Reset Applied Filters July 6-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More July 6-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More July 7-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More July 7-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More July 8-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More July 8-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More July 9-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More July 9-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More July 10-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More July 10-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More July 11, 2026-January 2, 2027 Chestertown Farmers Market Chestertown Learn More July 11-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More Pagination First Previous … Page 13 Page 14 Page 15 Page 16 Current page 17 Page 18 Page 19 Page 20 Page 21 … Next Last
