December in Annapolis: A Month of Magic, Lights, and Holiday Spirit
December in Annapolis: A Month of Magic, Lights, and Holiday Spirit
As December arrives, Annapolis transforms into a sparkling haven of holiday cheer. Twinkling lights line the streets, festive music fills the air, and the community comes alive with celebrations that embody the spirit of the season. Whether you're a resident or a visitor, there's no better time to immerse yourself in the charm and magic of Annapolis.
Here’s your guide to the must-attend events happening in and around Annapolis this December:
🎄 Grand Illumination & Tree Lighting
Kick off the holiday season with the annual Grand Illumination & Tree Lighting. Join the community as the city’s towering Christmas tree is illuminated in all its glory, marking the start of the festivities. Enjoy carolers, hot cocoa, and the excitement of the season.
📅 When: Dec 1st
🌐 More Info: Visit Annapolis Events
🌙 Midnight Madness
Experience the magic of late-night shopping in Downtown Annapolis during Midnight Madness. Stroll through historic streets decked with holiday décor, enjoy special sales, and soak in the festive ambiance. Keep an ear out for live music and carolers that bring an extra sparkle to the night.
📅 When: December 5 | December 12 | December 19
🌐 More Info: Midnight Madness Annapolis
🛍️ Annapolis Holiday Market
For unique gifts and artisanal finds, the Annapolis Holiday Market is a must-visit. Browse a variety of local vendors offering handcrafted items, festive treats, and more. It’s the perfect opportunity to shop small and support local businesses.
📅 When: December 12 - 15
🌐 More Info: Annapolis Market Info
✡️ Town Center Menorah Lighting
Celebrate the Festival of Lights with the annual Menorah Lighting at the Annapolis Town Center. This heartwarming event brings the community together to honor tradition with blessings, songs, and refreshments.
📅 When: During Hanukkah (December 25 - January 2)
🌐 More Info: Annapolis Town Center
🚤 Eastport Yacht Club Lights Parade
A highlight of the holiday season, the Eastport Yacht Club Lights Parade is a spectacle like no other. Watch beautifully decorated boats sail through the Annapolis harbor, their lights reflecting on the water in a dazzling display of creativity and festivity.
📅 When: December 14
🌐 More Info: Eastport Yacht Club
🎶 St. Anne’s Church Holiday Performance
Step into the historic St. Anne’s Church for an unforgettable holiday performance. With heavenly acoustics and an intimate setting, this event is sure to put you in the Christmas spirit.
📅 When: Dates vary
🌐 More Info: St. Anne’s Events
🚗 Lights on the Bay
Drive through Sandy Point State Park to experience Lights on the Bay, a beloved Annapolis tradition. This two-mile scenic route features dazzling light displays, including a glowing Chesapeake Bay Bridge and whimsical holiday characters.
📅 When: Late November–Early January
🌐 More Info: Lights on the Bay
🏠 Homestead for the Holidays
Discover the charm of Homestead Gardens, beautifully decorated for the season. From holiday workshops to festive décor, this event offers family-friendly activities and inspiration to deck your own halls.
📅 When: Throughout December
🌐 More Info: Homestead Gardens
🎅 Santapolis at Westfield Mall
Bring the kids to meet Santa at Westfield Annapolis Mall! Enjoy photo opportunities, holiday crafts, and the joy of seeing little ones share their wish lists with Santa himself.
📅 When: Daily in December
🌐 More Info: Westfield Mall Events
🩰 Maryland Hall Nutcracker Ballet
No holiday season is complete without a performance of "The Nutcracker." Maryland Hall’s production features talented dancers and timeless music, transporting audiences to a winter wonderland.
📅 When: December 14 - December 22
🌐 More Info: Maryland Hall
December in Annapolis is more than a month—it’s a celebration of community, tradition, and the magic of the holidays. Whether you’re shopping at the Midnight Madness event, enjoying the lights displays, or participating in the various festive activities, Annapolis offers a little something for everyone during the holiday season. Remember to check the respective websites for more details and any updates on these events.
Jen Holden, Realtor® | Principal
The Jen Holden Group of Compass
📱 443.803.7620 (m) | 📞 410.429.7425 (o)
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