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: July (722) August (610) September (336) October (225) November (118) December (105) January (13) February (11) March (14) April (14) May (9) June (8) Cities Chestertown (1) Crisfield (1) Rock Hall (4) St. Michaels (135) Regions Eastern Shore (141) Types Fairs & Festivals (47) Food & Drink (247) History & Heritage (252) Literary Arts (1) Multicultural (3) (-) Nature & Outdoor (133) Ongoing (48) (-) Performing Arts (8) Visual Arts (122) Narrow Your Event Search Start Date End Date Search By Keyword Quick Search This Week Next Week This Month Next Month Reset Applied Filters September 27, 2025 Crisfield Heritage Festival Crisfield Learn More September 27-30, 2025 Wine Tasting Cruises St. Michaels Learn More September 28-30, 2025 Wine Tasting Cruises St. Michaels Learn More September 29-30, 2025 Wine Tasting Cruises St. Michaels Learn More September 30, 2025 Wine Tasting Cruises St. Michaels Learn More October 11, 2025 Rock Hall FallFest Rock Hall Learn More December 12-14, 2025 Christmas in St. Michaels St. Michaels Learn More December 13-14, 2025 Christmas in St. Michaels St. Michaels Learn More December 14, 2025 Christmas in St. Michaels St. Michaels Learn More Pagination First Previous … Page 4 Page 5 Page 6 Page 7 Page 8 Page 9 Page 10 Page 11 Current page 12 next Last
