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 (188) February (321) March (212) April (149) May (176) June (167) July (140) August (145) September (119) October (158) November (77) December (48) Cities Chestertown (2) St. Michaels (430) Regions Eastern Shore (432) Types Fairs & Festivals (1) Food & Drink (484) History & Heritage (60) Multicultural (10) Nature & Outdoor (430) (-) Ongoing (432) Performing Arts (2) Visual Arts (60) Narrow Your Event Search Start Date End Date Search By Keyword Quick Search This Week Next Week This Month Next Month Reset Applied Filters January 25-February 22, 2026 Elegant Afternoon Tea at Brampton 1860 Chestertown Learn More February 22, 2026 Elegant Afternoon Tea at Brampton 1860 Chestertown Learn More April 15-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More April 15-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More April 16-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More April 16-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More April 17-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More April 17-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More April 18-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More April 18-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More April 19-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More April 19-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More Pagination First previous Current page 1 Page 2 Page 3 Page 4 Page 5 Page 6 Page 7 Page 8 Page 9 … Next Last
