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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

Previous Post:Save The Date List
Next Post:Eye on Annapolis: Top 5 in the News | December 17th, 2025 |

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First stop: St. Michaels! 🌊⚓️

Looking for the perfect summer day trip? We’ve mapped out everything you need, from where to grab your morning coffee and the can’t-miss stops at the Chesapeake Bay Maritime Museum to waterfront dining, boutique shopping, sweet treats, and even sunset sails.

Whether you’re planning a family adventure, a girls’ day, or a date on the Eastern Shore, St. Michaels is the kind of place you’ll want to visit again and again.

Ready to hit the road? The full day-trip guide is linked in our bio! Save this post for your next weekend adventure, and tell us where we should go next for Road Trip Ready with Annapolis Moms! 🚙☀️

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