Maryland Seafood Festival
The Maryland Seafood Festival hosts loads of seafood vendors, local shopping and vendor options, live music, a fantastic beverage selection, contests, kids activities, and more! This event will take place …
Annapolis Spring Sailboat Show
The Annapolis Spring Sailboat Show provides a local, fun, and accessible entry point to the sailing lifestyle. Located in the heart of America’s sailing capital, the event offers opportunities to …
Annapolis Irish Festival
The Annapolis Irish Festival roars back in 2026 with your beloved Irish bands and a lot of craic! Enjoy Carbon Leaf, Gaelic Storm, Scythian, Dublin 5, and more! This Irish celebration goes Friday night and all day Saturday! Join us Friday night for our first responder and military night featuring two incredible bands. Then return Saturday for a full day of Irish fun for all ages. Enjoy great live music, delicious food and drinks, and exciting Irish-themed vendors and activities. Get …
Day on the Bay to St. Michaels
Cruise across the Chesapeake Bay to St. Michaels on the Eastern Shore. Enjoy one complimentary non-alcoholic beverage on the way there! This quaint historic village offers fresh seafood, boutique shopping, …
Last-Minute Gift Ideas
Uh oh…is Christmas around the corner, already? It seems like only yesterday you were setting the table for Thanksgiving! You’ve got to get those presents wrapped and ready to put …
SoCo Holiday Market
Calling all fellow procrastinators! Come join us for our 5th annual last minute Holiday Market! If you are a gift getting procrastinator like me, this market is perfect for you! …
Jeff’s Christmas Light Show Spectacular
Don’t miss Jeff’s Christmas Light Show Spectacular! Show starts at 7:00 pm, runs for 15 minutes, and repeats until 9:00 pm. The market and walk-through display open at the end …
Gents’ Last Call: Sliders & Spirits at Zachary’s Jewelers
Finish your holiday shopping in style at Zachary’s Jewelers’ annual Gents’ Last Call event, an Annapolis tradition for last-minute shoppers. From December 22-23 (10 AM-8 PM) and December 24 (10 …
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 …