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 …
Locally Gathered HERE. a pop-up shop
Don’t miss Locally Gathered HERE. a pop-up shop! It will be open from October 16 to November 8, 2026. There will be so many amazing makers and fun events! (DNML)
Annual Craft Bazaar
Don’t miss the Annual Craft Bazaar at Broadneck High School! Shop handmade gifts and decor! (DNML)
Annapolis’ Holiday Market
Visit Annapolis’ West Street this holiday season and enjoy a special outdoor Holiday Market on Thursday night, December 10 and 17 when the first block of West Street transforms into …
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 …
Blanca Flor Pop-Up at Hobo Annapolis
Blanca Flor Silver Jewelry is popping up at Hobo Annapolis for a special one-day shopping event in downtown Annapolis. Shop a curated collection of Mexican silver and artisan jewelry from …
Annapolis Moms Deal Drop | Oct. 1, 2026
It might be the beginning of Spooky Season, but don’t forget that October is also Breast Cancer Awareness Month. Anne Arundel County offers no-cost cancer screenings to those who are …
Small Business Saturday
Small Business Saturday has become an annual event for our downtown Annapolis business districts. It has been over 12 years since we started celebrating our small local businesses on this …
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 …