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 we’re most looking forward to over the next couple of weeks that will make your season merry and bright.
December 6
West Annapolis Holiday Market
11 AM to 4 PM
Located in the parking lot of 20 Ridgely, at the corner of Annapolis Street and Giddings Avenue, the annual West Annapolis Holiday Market invites locals and visitors alike to visit over 30 artisans. You’ll find handcrafted gifts, seasonal décor, warm drinks, and plenty of goodies. Making this the perfect stop for holiday shopping or a leisurely December morning.
This market tends to draw a neighborhood vibe, making it ideal for families, couples, or anyone looking for a more relaxed shopping experience than the usual downtown bustle.
Naptown Vinyl Record Show
Noon to 5 PM
Music lovers, this one’s for you! The Naptown Vinyl Record Show at Crooked Crab Brewing brings together record vendors from across the DMV for a day of crate-digging, music nostalgia, and great vibes. Whether you’re hunting for a rare pressing, rediscovering old favorites, or just curious about vinyl culture, you’ll find plenty to explore.
As you browse, enjoy fantastic craft beer from Crooked Crab and savor delicious brick-oven pizza. It’s the perfect pairing for a laid-back afternoon surrounded by music and community.
Vintage Christmas Market
1 to 4 PM
Join Wildberry Farm + Market for an outdoor market on their farm. Their final market of the season, you’ll find find unique ornaments, handmade winter decor, or one-of-a-kind gifts. It’s the perfect spot for a rustic, cozy, and vintage-inspired holiday atmosphere that makes you feel like you’re inside the Hallmark Channel. You’ll also find beer, wine, and hot chocolate available so you can sip while you shop. You may even spot the big man himself roaming around.
December 7
Italian Christmas Market
10 AM to 3 PM
Celebrate the season Italian-style! Enjoy a festive bazaar filled with live Italian holiday music and vendors offering handmade items that are perfect for holiday shopping.
Savor Italian favorites like meatball and sausage-and-pepper subs, fresh zeppole, calamari, and specialty beverages. Inside the Lodge, browse a delicious selection of dolci, including their famous cannoli and cannoli kits, biscotti, cakes, and homemade treats. Pair your sweets with espresso or Italian coffee.
Families can also visit Babbo Natale (Santa Claus) for photos. Proceeds benefit Alzheimer’s Research, American Lung Association, and additional local charities.
Chocolate Binge Festival
11 AM to 4 PM
Sweet lovers, take note: the Annapolis Chocolate Binge Festival is here once again over on West Street. With dozens of chocolatiers, candy makers, bakers, and confectionery vendors, this festival transforms downtown Annapolis into a cocoa-lover’s paradise. Local artisans will be there with a wide range of handmade items including jewelry, pottery, candles, wood turnings, ornaments, clothing and more.
Tickets for the festival are $5 and should be purchased in advance since they sometimes sell out. It’s a perfect opportunity to enjoy indulgent treats in a merry downtown setting.
December 9
10th Annual Brigade Holiday Market
10 AM to 4 PM
NABSD proudly presents the 10th Annual Brigade Holiday Market, a festive holiday gift market held inside the beautiful Dahlgren Hall at the U.S. Naval Academy. This special event brings together local businesses and talented craftspeople, offering Midshipmen and visitors alike the chance to shop for unique, handcrafted gifts. The market is open to the public with free admission, and guests can enjoy complimentary hot chocolate and cookies as they browse.
Please note: Access to the Naval Academy requires a U.S. Real ID, Enhanced Driver’s License, or U.S. Passport. Foreign nationals are not authorized for tourist entry.
December 11
West Street Holiday Market
6 to 10 PM
Celebrate the season on Thursday, December 11 and 18 during Annapolis’ festive Midnight Madness with the lively West Street Holiday Market. This free event brings West Street to life with holiday décor, live entertainment, art vendors, and plenty of seasonal treats. Grab dinner at one of the many local restaurants, enjoy a cocktail, and browse shops and vendor booths as the street fills with music and lights.
Feeling adventurous? Take a spin down the crowd-favorite Human Hamster Ball Run and challenge friends or family to a race! Popcorn, oysters, unique gifts, and holiday cheer make this a can’t-miss night out. Come ready to shop, dine, dance, and soak in the spirited energy of downtown Annapolis.
The market will also be available on Thursday, December 18.
December 13
Annapolis Holiday Market
11 AM to 9 PM
The beloved Annapolis Holiday Market returns for two festive weekends, now at its new 2025 location on the front lawn of St. John’s College. This year’s market will feature over 100 artisans, specialty food vendors, and plenty of holiday entertainment. Stroll through rows of local and regional makers offering art, crafts, handmade gifts, and delicious seasonal foods. Warm up with hot chocolate, hot apple cider, spiced wine, strudels, and more as you explore the festive open-air market.
Additional Annapolis Holiday Market dates:
- Thursday, December 18, from 4 to 10 PM
- Friday, December 19, from 11 AM to 9 PM
- Saturday, December 20, from 11 AM to 9 PM
- Sunday, December 21, from 11 AM to 5 PM
Whether you’re after handmade gifts, cozy farm-market vibes, decadent chocolate, or festive downtown charm, Annapolis’ holiday events cover a wide range of tastes.
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