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 …
Zachary’s Jewelers Midnight Madness Night Two
Join Zachary’s Jewelers for Night Two of Midnight Madness on Thursday, December 11, featuring complimentary pours and festive treats, a special guest experience at the Breitling Bar, a gift with …
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 …
Zachary’s Jewelers Midnight Madness One
Join Zachary’s Jewelers for night one of Midnight Madness on Thursday, December 4, featuring complimentary pours and festive treats, a special guest experience at the Breitling Bar, a gift with …
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 …