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 …
Naptown Flea
Naptown Flea is coming to Eastport for the first time! Shop 20+ local vintage sellers, small businesses, and creators on Sunday, October 11 from 10:00 am–4:00 pm at MRE Mercantile. …
Annapolis Moms Deal Drop | Sept. 17, 2026
We’ve got a long weekend (at least for your public school kiddos), then it will finally be here—fall! And a lot of local businesses are gearing up not only for …
Annapolis Moms Deal Drop | Sept. 10, 2026
This weekend might be packed full of activities, but don’t forget about Grandparents Day! Maybe your child’s school or daycare invited grandparents and grandfriends into the classroom. But if not, …
PUMC Craft Fair
Don’t miss the Pasadena United Methodist Church (PUMC) annual craft fair. Come join us for craft vendors and homemade soup!
Naptown Vinyl Record Market
Don’t miss the Naptown Vinyl Record Market! Join us on the front lawn for a day of crate digging, good music, and great finds in a fun and welcoming atmosphere. …
AACLC Book Fair
Our sixth annual fundraiser book fair is on Saturday, September 26 from 10:00 am until 4:00 pm at Annapolis Mall, inside, near Discoveries: The Library at the Mall and Crate …
Annapolis Moms Deal Drop | Sept. 3, 2026
It’s Labor Day weekend, and we’ve got sidewalk sales and summer clearance events to finish out the summer. But with the warm weather not quite letting up, we think there’s …
Mad Cute Market
Mad Cute Market is a space for the people of Annapolis, MD to embrace their inner whimsy! Every month, we bring together a new mix of local small businesses that …
Annapolis Moms Deal Drop | Aug. 27, 2026
Earlier this week, we were feeling fall and ready to break out the flannel. Temperatures and humidity have gone up since then, but you can’t convince us that pumpkin season …