Maryland Ave Fall Festival
Don’t miss the Maryland Ave Fall Festival! There will be vendors, food trucks, live music, and entertainment! This is a Maryland Avenue tradition and a great time for the whole …
Fall Plant Sale
Join us for the Annual Plant Sale at Historic London Town & Gardens! Our Plant Sale is one of the most important fundraisers of the year, with all proceeds supporting …
Annapolis Moms Deal Drop | Sept. 24, 2026
This Tuesday is National Coffee Day! We know…every day is coffee day for us moms. But this is another great reason to get yourself a li’l treat. Below, you’ll also …
Third Sunday Market
Featuring over 20 local artists, artisans, bakers, brewers, chefs, crafters, distillers, farmers, watermen, and winemakers, the Third Sunday Market is a fantastic local shopping experience! Gather up your friends and …
Midnight Madness
Downtown Annapolis Partnership proudly presents Midnight Madness—a historic downtown Annapolis holiday tradition that captures the charm and character of our most beloved Norman Rockwell and Charles Dickens memories. We will …
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 4th from 10 AM–4 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!