National Hard Crab Derby - Crisfield, MD - Aug 27 to Sep 5, 2021
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 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.
Wine on the Beach - Ocean City, MD - Sep 10 to Sep 11, 2021
Head to the Inlet, where wine offerings and regional cuisine abound, plus arts and crafts vendors, micro-brews for purchase, live music and more!
Maryland Wine Festival - Westminster, MD - Sep 18 to Sep 19, 2021
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.
Native American Festival - Vienna, MD - Sep 18 to Sep 19, 2021
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 30 to Oct 3, 2021
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.
Chesapeake Film Festival - Easton, MD - Oct 1 to Oct 10, 2021
For 2021, both virtual and in person programming. The annual program focuses on stories about the Maryland region and local communities
Mid-Atlantic Small Craft Festival - St Michaels, MD - Oct 1 to Oct 3, 2021
Small craft, big fun. Join small boat enthusiasts and unique watercraft
Dorchester Out of the Darkness Walk for Awareness - Hurlock, MD - Oct 2 to Oct 2, 2021
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
Hurlock Fall Festival and Train Rides - Hurlock, MD - Oct 2 to Oct 2, 2021
The parade kicks off on Main St at 10am; train rides from Hurlock to Federalsburg leave the station on Gay Street at 11am, 12:30pm, 2, 3:30 and 5pm ($8 Round Trip). Enjoy food, music, fishmobile, bubble show, zoo to you, scales & tales display, pony rides, more
ARToberFEST - Stevensville, MD - Oct 2 to Oct 2, 2021
Enjoy this celebration of local food, music, artisans and breweries in historic Stevensville.
Endless Summer Cruisin’ - Ocean City, MD - Oct 7 to Oct 10, 2021
Massive car show with over 2000 hot rods, custom cars, trucks and more, plus vendors
Good Beer Festival - Salisbury, MD - Oct 8 to Oct 9, 2021
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 9 to Oct 9, 2021
Oysters and other food, beer, raffles and more.
Fall Fest with Oysters - Rock Hill, MD - Oct 9 to Oct 9, 2021
A celebration of family, community and oysters. Enjoy music, crafts, food and fun on Main Street in Rock Hall which includes a kids’ court and more, rain or shine
Berlin Oktoberfest - Berlin, MD - Oct 16 to Oct 16, 2021
Music, German food, craft vendors, annual Fall sidewalk sale, beer garden, games and activities such as face painting, scarecrow making, pumpkin painting and others for the kids. Annual cornhole tournament at Burley Tavern. Free parking at Berlin Intermediate School with shuttle to downtown.
OysterFest at Chesapeake Bay Maritime Museum - St Michaels, MD - Oct 17 to Nov 2, 2021
Celebrate the Chesapeake oyster featuring Sip, Slurp, & Savor! Live music, boat rides, retriever demos, oysters and local fare, oyster stew competition, cooking demos, childrens activities. Rain or shine.
OC-Toberfest - Ocean City, MD - Oct 22 to Oct 24, 2021
A celebration of October and Halloween with a beach maze, pet parade, Great Pumpkin Race and Halloween costume party for kids. Events vary by day.
Winterfest of Lights - Ocean City, MD - Nov 18 to Jan 1, 2022
The 2021 Winterfest of Lights will be an expanded walking tour that takes you through thousands of sparkling holiday lights and many animated light displays located along a paved path in Northside Park. Sip hot chocolate, take a photo with Santa, visit our gift shop and enjoy the array of holiday exhibits – including many surprises. Come see the 50-foot Christmas tree put on a show for you and soak up all of the holiday spirit at Winterfest of Lights.