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Arts & Entertainment, Community, Do Not Miss

Do Not Miss List

December 14, 2025 by Piper Langenfeld

Week of 12/18-12/22

Presented by

Thursday, December 18

Santapolis: A Magical Holiday Experience | Annapolis Mall (Dec. 18-24)

Great Annapolis Gingerbread Houses | Annapolis Visitors Center (Dec. 18-20)

SPCA of Anne Arundel County Presents Lights on the Bay | Sandy Point State Park (Dec. 18-Jan. 1)

Sleigh Bells Ring HERE. a pop-up shop | 6 Fleet Street, Annapolis (Dec. 18-21)

Annapolis Holiday Market | St. John’s College (Dec. 18-21)

Midnight Madness | Downtown Annapolis 

North Pole Lights Walk | Willow Oak Flower & Herb Farm (Dec. 18-23)

Midnight Madness Holiday Artisan Market | 53 West Street, Annapolis

Davy Dance Academy Presents the Elf on a Maryland Shelf Musical | Anne Arundel Community College: Pascal Center for Performing Arts (Dec. 18 & 19)

Watermark Presents the Jolly Express Cruise | 1 Prince George Street (Dec. 18-24)

Friday, December 19 

Day Off Discoveries | Annapolis Area Christian School (Dec. 19-23)

Historic Annapolis Presents the Holiday Traditions Tour | William Paca House & Garden (Dec. 19-22)

Navy Men’s Basketball vs Coppin State | United States Naval Academy: Alumni Hall 

The Talent Machine Co. Presents A Merry Mix-Up | Indian Creek School (Dec. 19-23)

Annapolis Symphony Orchestra Presents Holiday Pops | Maryland Hall

White Christmas | Classic Theatre of Maryland (Dec. 19-24)

Garden Chores & Coffee: Decorating with Winter Greens | Homestead Gardens: Davidsonville 

Ugly Sweater Party | Federal House 

Saturday, December 20 

Road Runners Club of America Presents the Naptown Half Marathon & 10K/5K | Navy-Marine Corps Memorial Stadium

STEAM: The Hidden Life of Spices | Eastport-Annapolis Neck Library 

Navy Wrestling vs Morgan State | United States Naval Academy: Alumni Hall 

Annapolis Symphony Orchestra Presents Holiday Pops | Severna Park High School

Ballet Theatre of Maryland Presents The Nutcracker | Maryland Hall (Dec. 20 & 21)

Live Arts Maryland Presents Handel’s Messiah | St. Anne’s Episcopal Church (Dec. 20 & 21)

Annapolis Moms Media Presents A SQRRL! Holiday | Rams Head On Stage 

Watermark Presents the Holiday Walking Tour | 188 Main Street

Sunday, December 21 

Navy Men’s Basketball vs Rosemont College | United States Naval Academy: Alumni Hall

Annapolis Symphony Orchestra Presents Holiday Pops | Bowie State University 

Jon McLaughlin & Friends Holiday Show with T.3 | Rams Head On Stage

Monday, December 22 

School’s Out Workshop: Revolting Children | Children’s Theatre of Annapolis

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Related posts:

Midnight Madness Preview Save The Date List Thankful for Carryout: Where to Grab Your Turkey Day Meal! Single During the Holidays
Category: Arts & Entertainment, Community, Do Not MissTag: Activities, Annapolis, Family Friendly See all posts by Piper Langenfeld

About Piper Langenfeld

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Next Post:Eye on Annapolis: Top 5 in the News | December 17th, 2025 |

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🎉 Hi Moms! 🎉

🎉 Hi Moms! 🎉

@americanremodelllc is proud to be a sponsor of this amazing community! 💙 They’ve already helped 100+ moms in our group transform their homes and they’d love to help even more families here.

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✨ New Year, New Home Perk! ✨
To kick off the year, members of our group can enjoy an extra $500 OFF any remodeling project now through 1/31.

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🎶 Local legends,

🎶 Local legends, unite! 🎶

Locals galore! Community Supporter Rams Head On Stage is turning up the volume with an incredible lineup of amazingly talented local musicians hitting the stage over the next couple of months. 🎸✨ Grab your friends, cheer on your favorites, and show some hometown love while enjoying live music you won’t want to miss.

🎟️ Get your tickets now and be part of the buzz 👉 www.ramsheadonstage.com/events

Let’s support local and make it loud! 🎤
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