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: June (449) July (780) August (542) September (297) October (200) November (108) December (101) January (11) February (8) March (9) April (12) May (9) Cities Cambridge (23) Chestertown (90) Crisfield (5) Oxford (3) Princess Anne (13) Rock Hall (7) Salisbury (3) St. Michaels (243) Regions Eastern Shore (387) Types Fairs & Festivals (50) Food & Drink (296) History & Heritage (272) Multicultural (3) Nature & Outdoor (177) Ongoing (71) Performing Arts (8) Visual Arts (114) Narrow Your Event Search Start Date End Date Search By Keyword Quick Search This Week Next Week This Month Next Month Reset Applied Filters June 16-November 30, 2025 Private Catamaran Sailing Tour in St. Michaels, Maryland St. Michaels Learn More June 16-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More June 17-November 30, 2025 Private Catamaran Sailing Tour in St. Michaels, Maryland St. Michaels Learn More June 17-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More June 18-November 30, 2025 Private Catamaran Sailing Tour in St. Michaels, Maryland St. Michaels Learn More June 18-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More June 19-November 30, 2025 Private Catamaran Sailing Tour in St. Michaels, Maryland St. Michaels Learn More June 19-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More June 20-November 30, 2025 Private Catamaran Sailing Tour in St. Michaels, Maryland St. Michaels Learn More June 20-September 30, 2025 Wine Tasting Cruises St. Michaels Learn More June 20-December 13, 2025 Saint Michaels Ghost Walk - Spirits of Rowdy Women St. Michaels Learn More June 21-November 22, 2025 St. Michaels Farmers Market St. Michaels Learn More Pagination First previous Current page 1 Page 2 Page 3 Page 4 Page 5 Page 6 Page 7 Page 8 Page 9 … Next Last
June 16-November 30, 2025 Private Catamaran Sailing Tour in St. Michaels, Maryland St. Michaels Learn More
June 17-November 30, 2025 Private Catamaran Sailing Tour in St. Michaels, Maryland St. Michaels Learn More
June 18-November 30, 2025 Private Catamaran Sailing Tour in St. Michaels, Maryland St. Michaels Learn More
June 19-November 30, 2025 Private Catamaran Sailing Tour in St. Michaels, Maryland St. Michaels Learn More
June 20-November 30, 2025 Private Catamaran Sailing Tour in St. Michaels, Maryland St. Michaels Learn More