Naptown Flea w/ Annapolis Idiot
In collaboration with Naptown Vinyl & Vintage and Maryland Hall, Naptown Flea goes indoors for the first time! Come dig, shop, vibe, and kick off the season with the best …
Midnight Madness Preview
If you’re looking for a holiday experience that feels like stepping straight into a snow globe someone shook a little too enthusiastically, downtown Annapolis is about to become your happy …
Annapolis Holiday Market
The Annapolis Holiday Market will feature 100 artisan vendors, specialty food stalls, and festive entertainment. Visitors can shop for handcrafted gifts, including jewelry, pottery, glass art, and home décor, while …
Heroes Holiday Market
Don’t miss the Heroes Holiday Market! It will take place on December 14, 2025 from 8:00 am to 11:00 am at Heroes Pub. There will be different vendors, custom cocktails, …
Museum Store Sunday has Unique Gifts for Great Causes
Do you need something to do with your kiddos but also need to check off that holiday shopping list? After Black Friday and Small Business Saturday, keep your support local …
Supporting Local on Small Business Saturday
Kick off the holiday season downtown by participating in Small Business Saturday! On November 29, celebrate the local shops and businesses that give our community its unique character. From boutique …
Tiny Art Show + Artisan Market
Discover the joy of small-scale creativity at our Tiny Art Show + Artisan Market. This festive showcase features 14 local artists presenting original wall art—perfect for gift giving, collecting, or …
Give Back Event for Bernie House
Don’t miss this Give Back Event for Bernie House on December 5, 2025 from 5:00 pm to 8:00 pm. This Give Back Event for Bernie House will take place at …
Sleigh Bells Ring HERE. a pop-up shop
Don’t miss the Sleigh Bells Ring HERE. a pop-up shop! It will be open from 11/14-12/21 from 10:00 am to 6:00 pm daily. This shop will benefit Bernie House.
First Saturday Artist Event
Don’t miss this First Saturday Artist Event! Stop by Honey’s Harvest Farm on December 6, 2025 between 10:00 am – 2:00 pm to meet local potter Marguerite Marinakis. She will …