Holiday Markets in Annapolis
There’s no shortage of festive fun and shopping opportunities in Annapolis this December. From classic holiday bazaars to chocolate-filled strolls, here’s a look at some of the markets and festivals …
Midnight Madness Holiday Artisan Market
Start your Midnight Madness in Annapolis on West Street! Grab a bite to eat at our restaurants, enjoy a few cocktails, and check out our shops and vendors. Dare to …
Brigade Holiday Market
Join us in Dahlgren Hall at the US Naval Academy for the holiday event of the season! Shop local at the Brigade Holiday Market. Complimentary cookies, hot chocolate, and hot …
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, …
Holiday Market
From hot chocolate to holiday shopping to a visit with Santa Claus (11:00 am – 1:00 pm), you won’t want to miss this year’s Holiday Market! Located in the parking …
10th Annual Brigade Holiday Market
Join us in the gorgeous Dahlgren Hall at the US Naval Academy for the event of the season! Get all of your holiday shopping done with hot cocoa while supporting …
Jingle Jubilee
Celebrate the season with QAC Parks and Recreation at our Jingle Jubilee on Saturday, December 13, 2025 from 3:00 pm – 7:00 pm at the Matapeake Beach and Clubhouse! This free, family-friendly event is open …
Naptown Vinyl Record Show & Vintage Market
Hosted by Maryland Hall, Naptown Vinyl & Vintage is Annapolis’ premier record shopping opportunity. Come dig through hundreds of crates to find that hidden gem you have been looking for. The …
Deale Volunteer Fire Department’s Fall Market
Don’t miss the Deale Volunteer Fire Department’s Fall Market! There will be pumpkins, apple cider, vendors, yard sales, snacks, and so much more!