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 (80) Crisfield (5) Kennedyville (1) Oxford (3) Rock Hall (4) St. Michaels (155) Regions Eastern Shore (248) 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 23-30, 2025 Wine Tasting Cruises St. Michaels Learn More September 24-30, 2025 Wine Tasting Cruises St. Michaels Learn More September 24, 2025 J. Millard Tawes Crab & Clambake Crisfield Learn More September 25-30, 2025 Wine Tasting Cruises St. Michaels Learn More September 26-30, 2025 Wine Tasting Cruises St. Michaels Learn More September 27-November 22, 2025 St. Michaels Farmers Market St. Michaels Learn More September 27, 2025-January 2, 2027 Chestertown Farmers Market Chestertown 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 4-November 22, 2025 St. Michaels Farmers Market St. Michaels Learn More Pagination First Previous … Page 10 Page 11 Page 12 Page 13 Current page 14 Page 15 Page 16 Page 17 Page 18 … Next Last
