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 (736) August (610) September (336) October (225) November (118) December (104) January (13) February (11) March (14) April (14) May (9) June (8) Cities Chestertown (79) Crisfield (4) Oxford (15) Princess Anne (11) Salisbury (3) (-) St. Michaels (142) Regions Eastern Shore (142) Types Fairs & Festivals (23) Food & Drink (157) (-) History & Heritage (142) Nature & Outdoor (134) Ongoing (48) Performing Arts (3) 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-December 13, 2025 Saint Michaels Ghost Walk - Spirits of Rowdy Women St. Michaels Learn More August 10-September 30, 2025 Wine Tasting Cruises St. Michaels 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 August 15-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More August 15-December 13, 2025 Saint Michaels Ghost Walk - Spirits of Rowdy Women St. Michaels Learn More August 16-November 22, 2025 St. Michaels Farmers Market St. Michaels Learn More August 16-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More August 16-December 13, 2025 Saint Michaels Ghost Walk - Spirits of Rowdy Women St. Michaels Learn More August 17-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More Pagination First Previous Page 1 Page 2 Page 3 Page 4 Current page 5 Page 6 Page 7 Page 8 Page 9 … Next Last
August 9-December 13, 2025 Saint Michaels Ghost Walk - Spirits of Rowdy Women St. Michaels Learn More
August 15-December 13, 2025 Saint Michaels Ghost Walk - Spirits of Rowdy Women St. Michaels Learn More
August 16-December 13, 2025 Saint Michaels Ghost Walk - Spirits of Rowdy Women St. Michaels Learn More