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 (365) March (222) April (151) May (178) June (167) July (140) August (145) September (122) October (159) 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 (66) Miscellaneous (3) 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 28-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More July 29-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More July 29-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More July 30-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More July 30-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More July 31-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More July 31-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More August 1, 2026-January 2, 2027 Chestertown Farmers Market Chestertown Learn More August 1-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More August 1-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More August 2-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More August 2-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More Pagination First Previous … Page 17 Page 18 Page 19 Page 20 Current page 21 Page 22 Page 23 Page 24 Page 25 … Next Last
