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 7, 2025 from 11:00 am to 4:00 …
Homestead Gardens’ Fall Festival Weekends
Join us for Fall Festival Weekends at Homestead Gardens: Davidsonville! Give your family the same enchanting experiences you had as a child—seeing the barnyard animals, taking hayrides, picking out pumpkins, …
Know Before You Go: Annapolis Songwriters Festival
Annapolis is turning the volume up! The Annapolis Songwriters Festival, presented by Rams Head Presents in partnership with BMI, Visit Annapolis & Anne Arundel County, and the City of Annapolis, …
AACS Fall Festival
Don’t miss the Annapolis Area Christian School Fall Festival! There will be great family friendly fun with moon bounces, games, crafts, face painting, and more!
Huzzah! A Merry Guide to the Maryland Renaissance Festival
Hear ye, hear ye! The Maryland Renaissance Festival is back, and whether you’re a seasoned faire-goer or just wondering what all the “huzzah!” is about, we’ve got you covered. The …
Fall Fun Fest
Don’t miss this Fall Fun Fest at A Little Farm and Nursery! There will be live entertainment, food trucks, carnival games, and more! RSVP here!
Oktoberfest
The most anticipated event of the season—Oktoberfest 2025 in West Annapolis!Craft RaR beer will be flowing, provided by our dear friends and neighbors at Chessie’s Wharf. • 100+ amazing vendors• …
Eastport Terrace & Harbour House Family Community Event
The Resident Service Team is hosting a family fun day event with food, games, and activities for children and adults. We invite community members to join us in providing service …
EpCult Center 2025
We’re showcasing all the deliciousness that Shopping Center Road has to offer with food from 4 Sisters, El Jefe, Tokyo Bay, DePaola’s Bagel & Brunch, Hardee’s, Dunkin Donuts, and the …
Inaugural Corn-Hooley & Shamrock Shenanigans
Don’t miss the Inaugural Corn-Hooley & Shamrock Shenanigans! A fun filled day of cornhole, family fun events, and good ole’ tomfoolery! The Inaugural Corn-Hooley & Shamrock Shenanigans will take place …