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 (552) August (625) September (340) October (226) November (119) December (106) January (13) February (11) March (14) April (14) May (9) June (8) Cities Chestertown (84) Crisfield (5) Oxford (14) Princess Anne (11) Rock Hall (7) Salisbury (3) St. Michaels (136) Regions Eastern Shore (260) Types (-) Fairs & Festivals (46) Food & Drink (235) (-) History & Heritage (240) Literary Arts (1) Multicultural (3) Nature & Outdoor (123) Ongoing (43) Performing Arts (8) Visual Arts (117) Narrow Your Event Search Start Date End Date Search By Keyword Quick Search This Week Next Week This Month Next Month Reset Applied Filters August 9, 2025-January 2, 2027 Chestertown Farmers Market Chestertown Learn More August 9-10, 2025 Pirates and Wenches Weekend Rock Hall Rock Hall Learn More August 9-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More August 9-December 13, 2025 Saint Michaels Ghost Walk - Spirits of Rowdy Women St. Michaels Learn More August 9-10, 2025 Prates and Wenches Weekend in Rock Hall Maryland! Rock Hall Learn More August 10, 2025 Pirates and Wenches Weekend Rock Hall Rock Hall Learn More August 10-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More August 10, 2025 Prates and Wenches Weekend in Rock Hall Maryland! Rock Hall Learn More August 11-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More August 12-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More August 13-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More August 14-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More Pagination First Previous … Page 2 Page 3 Page 4 Page 5 Current page 6 Page 7 Page 8 Page 9 Page 10 … Next Last
August 9-December 13, 2025 Saint Michaels Ghost Walk - Spirits of Rowdy Women St. Michaels Learn More