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 (352) March (245) April (172) May (195) June (198) July (154) August (157) September (130) October (165) November (77) December (48) January (1) Cities Chestertown (51) Crisfield (4) St. Michaels (430) Regions Eastern Shore (485) Types (-) Fairs & Festivals (4) (-) Food & Drink (485) History & Heritage (56) Miscellaneous (3) Nature & Outdoor (432) Ongoing (432) Performing Arts (3) Visual Arts (48) Narrow Your Event Search Start Date End Date Search By Keyword Quick Search This Week Next Week This Month Next Month Reset Applied Filters May 18-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 18-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 19-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 19-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 20-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 20-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 21-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 21-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 22-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More May 22-November 15, 2026 St. Michaels Wine Tasting Cruise on Epiphany! St. Michaels Learn More May 23, 2026-January 2, 2027 Chestertown Farmers Market Chestertown Learn More May 23-November 15, 2026 2 Hour Relaxing Chesapeake Day Sail on Epiphany! St. Michaels Learn More Pagination First Previous … Page 4 Page 5 Page 6 Page 7 Current page 8 Page 9 Page 10 Page 11 Page 12 … Next Last
