JessFest
Don’t miss JessFest! Join us for a fun event packed with “All the Things” Jess Stach Beard loved in this world while raising money for those she fought with and …
Day of the Dead Festival (Día de los Muertos)
Celebrate culture, community, and tradition! The Day of the Dead Festival (Día de los Muertos) is an annual Annapolis celebration with live music, traditional dance, altars, art, food, and family-friendly …
Fall Harvest Festival
You won’t want to miss the Annapolis Recreation & Parks Fall Harvest Festival! Sing along with Princesses Elsa, Mirabel, and Tiana, experience the Superhero Training Camp with Batman, Black Panther, …
Family Fall Festival
Join Waugh Chapel Towne Centre on South Main Chapel Way for our annual Family Fall Festival on Saturday, October 24, 2026 from 12:00 pm-2:00 pm! Visit for balloon art, live …
Paws and Pumpkins Fall Fest
Join us for a fun-filled day at the AmericanK9 Dog Ranch in Davidsonville as we celebrate the beauty of fall with our furry friends! The Paws and Pumpkins Fall Fest …
5th Annual Riviera Beach Fall Fest
Get ready for one of Riviera Beach’s favorite community traditions! Join us for an afternoon filled with fall fun, food, live music, games, local vendors, activities for the kids, and …
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 …