National Hard Crab Derby - Crisfield, MD - Aug 26 to Sep 1, 2019
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
National Folk Festival - Salisbury, MD - Sep 6 to Sep 8, 2019
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.
CrowFest - Kennedyville, MD - Sep 8 to Sep 8, 2019
Festival at Crow Vineyard & Winery with live music, vendors, wine, food, tours, grape stomping, games and hayrides.
Native American Festival - Vienna, MD - Sep 14 to Sep 15, 2019
The Native American Festival features traditional dancers, singers, drumming, crafts, artists’ demonstrations, authentic Native food, a large silent auction and more. This pow-wow is organized by the Nause Waiwash Band of Indians, made up of descendants of local Nanticoke Indians.
Sunfest - Ocean City, MD - Sep 19 to Sep 22, 2019
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.
Maryland Wine Festival - Westminster, MD - Sep 21 to Sep 22, 2019
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.
Dorchester Out of the Darkness Walk - Hurlock, MD - Sep 21 to Sep 21, 2019
Suicide prevention starts with us! Walk to fight suicide and raise awareness about mental health. Funds raised by the walk benefit the American Foundation for Suicide Prevention, plus a memorial table to honor loved ones and resource tables both before and after the walk
GrooveFEST Downtown Music Festival - Cambridge, MD - Sep 21 to Sep 21, 2019
Soul, funk, jazz and blues sound out throughout downtown Cambridge.
Wine on the Beach - Ocean City, MD - Sep 27 to Sep 28, 2019
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 3 to Oct 10, 2019
The annual program focuses on stories about the Maryland region and local communities
Chincoteague Island Oyster Festival - Chincoteague, VA - Oct 6 to Oct 16, 2018
46th annual event. Oysters and other food, beer, raffles and more.
Endless Summer Cruisin’ - Ocean City, MD - Oct 10 to Oct 13, 2019
Massive car show with over 2000 hot rods, custom cars, trucks and more, plus vendors
Good Beer Festival - Salisbury, MD - Oct 11 to Oct 12, 2019
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.
OC-Toberfest - Ocean City, MD - Oct 19 to Oct 27, 2019
A two weekend celebration of October and Halloween with a beach maze, pet parade, Great Pumpkin Race and Halloween costume party for kids. Events vary by day.
Sailwinds Park East Kite Festival - Cambridge, MD - Oct 27 to Oct 27, 2019
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