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 (142) February (366) March (225) April (151) May (178) June (167) July (140) August (145) September (122) October (159) November (77) December (48) Cities Chestertown (54) Crisfield (4) St. Michaels (430) Regions Eastern Shore (488) Types Fairs & Festivals (4) (-) Food & Drink (488) History & Heritage (65) Miscellaneous (3) Multicultural (7) Nature & Outdoor (432) Ongoing (433) Performing Arts (3) Visual Arts (57) 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 22-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More July 23-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More July 23-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More July 24-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More July 24-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More July 25, 2026-January 2, 2027 Chestertown Farmers Market Chestertown Learn More July 25-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More July 25-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More July 26-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More July 26-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More July 27-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More July 27-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More Pagination First Previous … Page 16 Page 17 Page 18 Page 19 Current page 20 Page 21 Page 22 Page 23 Page 24 … Next Last
