20th Annual Holiday Drive
Join us for a FREE family holiday event benefiting The Blue Ribbon Project! Kids of all ages are invited to become Holiday Explorers and embark on an unforgettable North Pole …
Capitol Hill Chamber Music Festival (Annapolis Shows)
The 2026 Capitol Hill Chamber Music Festival celebrates our shared humanity through the musical depiction of experiences of conflict resolution and compassion, featuring 17th and 18th-century chamber music performed by …
Mid-Autumn Moon Festival Celebration
Celebrate the Mid-Autumn Moon Festival with a cozy storytime. We’ll learn about this special harvest tradition, make paper lanterns, and even sample mooncakes! This event will take place at Discoveries. …
Annapolis Chocolate Binge Festival
The Inner West Street Association brings you the popular Annapolis Chocolate Binge Festival to downtown Annapolis for the holidays. Held on Sunday, December 6 from 11:00 am to 4:00 pm …
Maryland Korean Festival
Don’t miss the Maryland Korean Festival! There will be K-music, K-games, K-food, K-culture, and K-fun, including photo booths, face painting, crafts, and more! The Maryland Korean Festival will take place …
CBEC Fall Fest 2026
Don’t miss the CBEC Fall Fest! There will be oysters, live music, sunset sound healing, Halloween bingo, an adult yoga soul flow, and children’s yoga. Register here! This event will …
5th Annual Riviera Beach Community Fall Festival
Get ready to shop, eat, sip, and explore because this year’s lineup is ! We have an amazing mix of local businesses, talented makers, live music, delicious food vendors, crafters, …
Bluegrass by the Bay: Annapolis Baygrass Returns to Sandy Point
Did you know Annapolis is home to a 2026 Event of the Year nominee from the International Bluegrass Music Association? That’s right! The Annapolis Baygrass Music Festival is right around …
Harvest Festival
Enjoy FREE family fun with face painting, hay rides, a pumpkin patch, Trunk-o’-Treating, games & more!! Come celebrate the season with costumes, candy, and community fun!
Drug Education and Awareness Sporting Festival
Drug Free All Stars will be hosting the 2026 Drug Education and Awareness Sporting Festival on September 12, 2026 at Annapolis Recreation & Parks, Griscom 1, from 11:00 am-5:00 pm.