Eastern Shore Fall Festivals – Fall 2024 MD Events

Berlin Oktoberfest - Berlin, MD - Oct 19 to Oct 19, 2024
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.

Winterfest of Lights - Ocean City, MD - Nov 16 to Dec 31, 2023
The 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 the 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.

OysterFest at Chesapeake Bay Maritime Museum - St Michaels, MD - Oct 28 to Oct 28, 2023
Celebrate the Chesapeake oyster featuring Sip, Slurp, & Savor! Live music, boat rides, retriever demos, oysters and local fare, oyster stew competition, cooking demos, children’s activities. Rain or shine.

Tilghman Island Day - Tilghman, MD - Oct 21 to Oct 21, 2023
Arts and nautical crafts, boat building demonstrations, oyster shucking, crab picking and a look at the life of a waterman. The watermen’s boat docking contest is always a highlight

Dorchester Out of the Darkness Walk for Awareness - Hurlock, MD - Oct 21 to Oct 21, 2023
Suicide prevention starts with you! 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

Sunfest - Ocean City, MD - Oct 19 to Oct 22, 2023
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.

OC-Toberfest - Ocean City, MD - Oct 19 to Oct 22, 2023
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.

Sailwinds Park East Kite Festival - Cambridge, MD - Oct 15 to Oct 15, 2023
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

Fall Fest with Oysters - Rock Hill, MD - Oct 14 to Oct 14, 2023
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

Nanticoke River Jamboree - Vienna, MD - Oct 14 to Oct 14, 2023
Through historic craftspeople, docents in period dress, an open hearth cooking demonstration by African American interpreters, Native life skills and the history of the Eastern Shore waterways, visitors can immerse themselves in over 350 years of history.

Good Beer Festival - Salisbury, MD - Oct 13 to Oct 14, 2023
Over 100 different craft beers and unlimited tastings from master brewers. Features live music and other fun activities. Held at the Pemberton Historical Park.

Chincoteague Island Oyster Festival - Chincoteague, VA - Oct 7 to Oct 7, 2023
Oysters and other food, beer, raffles and more.

ARToberFEST - Stevensville, MD - Oct 7 to Oct 7, 2023
Enjoy this celebration of local food, music, artisans and breweries in historic Stevensville.

Mid-Atlantic Small Craft Festival - St Michaels, MD - Oct 6 to Oct 8, 2023
Small craft, big fun. Join small boat enthusiasts and unique watercraft

Endless Summer Cruisin’ - Ocean City, MD - Oct 5 to Oct 8, 2023
Massive car show with over 2000 hot rods, custom cars, trucks and more, plus vendors

Chesapeake Film Festival - Easton, MD - Sep 30 to Oct 8, 2023
For 2023, both virtual and in person programming. The annual program focuses on stories about the Maryland region and local communities

Native American Festival - Vienna, MD - Sep 16 to Sep 16, 2023
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.

Maryland Wine Festival - Westminster, MD - Sep 16 to Sep 16, 2023
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 8 to Sep 9, 2023
Head to the Inlet, where wine offerings and regional cuisine abound, plus arts and crafts vendors, micro-brews for purchase, live music and more!

National Hard Crab Derby - Crisfield, MD - Sep 1 to Sep 3, 2023
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

Hurlock Fall Festival and Train Rides - Hurlock, MD - Oct 1 to Oct 1, 2022
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

National Folk Festival - Salisbury, MD - Aug 26 to Aug 28, 2022
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.