National Hard Crab Derby - Crisfield, MD - Aug 31 to Sep 6, 2020
Features live entertainment, music, parade, fireworks, carnival rides, beauty pageant, races, contests and lots of family fun with crafts, arts, and more vendors. Famous for the crustacean race from which it gets its name
Maryland Wine Festival - Westminster, MD - Sep 19 to Sep 20, 2020
Sample over 150+ Maryland wines, enjoy a juried art show, listen to live music, snack on locally made food and artisanal cheeses, and more! Get a commemorative wine glass with sampling from all participating wineries! There is also a VIP package, and designated drivers get in for a reduced rate. Children under 12 get in free with a paid adult ticket. Held at the Carroll County Farm Museum. There is parking available onsite, plus free handicap-accessible shuttles from Carroll Community College and the Carroll County Office Building.
Wine on the Beach - Ocean City, MD - Sep 25 to Sep 26, 2020
Head to the Inlet, where wine offerings and regional cuisine abound, plus arts and crafts vendors, micro-brews for purchase, live music and more!
Chesapeake Film Festival - Easton, MD - Oct 1 to Oct 4, 2020
The annual program focuses on stories about the Maryland region and local communities
Sunfest - Ocean City, MD - Oct 1 to Oct 4, 2020
Free admission to this event that features great food, live music, hayrides, and lots of fun things to do. ;Held at the inlet lot on the south end of the boardwalk.
Endless Summer Cruisin’ - Ocean City, MD - Oct 8 to Oct 11, 2020
Massive car show with over 2000 hot rods, custom cars, trucks and more, plus vendors
Good Beer Festival - Salisbury, MD - Oct 9 to Oct 10, 2020
Over 100 different craft beers and unlimited tastings from master brewers. Features include a live music line-up, and the Sports Zone with telecasts of the biggest games of the weekend. Held at the Pemberton Historical Park.
Chincoteague Island Oyster Festival - Chincoteague, VA - Oct 10 to Oct 10, 2020
Oysters and other food, beer, raffles and more.
Sailwinds Park East Kite Festival - Cambridge, MD - Oct 18 to Oct 18, 2020
Free festival features kites of all shapes and sizes. Bring your own kite, buy one, or watch expert kite flyers, plus bungee bounce, face painting, food, music and more
National Folk Festival - Salisbury, MD - Sep 10 to Sep 12, 2021
Itinerant folk festival, held this year in Salisbury. One of the country’s largest, longest-running celebrations of arts, culture, and heritage offers three days of free fun with over 350 traditional musicians, dancers, craftspeople, and more, plus children’s activities, food and craft brews, dancing, storytelling, parades and more. Since 1934, this festival has celebrated Americans, no matter how long or how recently their families have lived on these shores. Free shuttles from Wicomico Youth & Civic Center to Downtown Salisbury.