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 (683) August (610) September (336) October (225) November (118) December (105) January (13) February (11) March (14) April (14) May (9) June (8) Cities Cambridge (21) Chestertown (84) Crisfield (5) Oxford (17) Rock Hall (7) Salisbury (3) St. Michaels (23) Regions Eastern Shore (160) Types (-) Fairs & Festivals (47) Food & Drink (243) History & Heritage (250) Literary Arts (1) Multicultural (3) Nature & Outdoor (129) Ongoing (46) 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 December 6, 2025-January 2, 2027 Chestertown Farmers Market Chestertown Learn More December 6, 2025 Cambridge Ghost Walk - Most Haunted Street in Maryland Cambridge Learn More December 12-14, 2025 Christmas in St. Michaels St. Michaels Learn More December 12-14, 2025 Oxford Holiday Market 2025 Oxford Learn More December 13, 2025-January 2, 2027 Chestertown Farmers Market Chestertown Learn More December 13-14, 2025 Christmas in St. Michaels St. Michaels Learn More December 13-14, 2025 Oxford Holiday Market 2025 Oxford Learn More December 14, 2025 Christmas in St. Michaels St. Michaels Learn More December 14, 2025 Oxford Holiday Market 2025 Oxford Learn More December 20, 2025-January 2, 2027 Chestertown Farmers Market Chestertown Learn More December 27, 2025-January 2, 2027 Chestertown Farmers Market Chestertown Learn More January 3, 2026-January 2, 2027 Chestertown Farmers Market Chestertown Learn More Pagination First Previous … Page 5 Page 6 Page 7 Page 8 Current page 9 Page 10 Page 11 Page 12 Page 13 … Next Last