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Arts & Entertainment, Community, Do Not Miss

Save The Date List

November 16, 2025 by Piper Langenfeld

Presented by

Wednesday, December 17 

Santapolis: A Magical Holiday Experience | Annapolis Mall (Dec. 17-24)

SPCA of Anne Arundel County Presents Lights on the Bay | Sandy Point State Park (Dec. 17-Jan. 1)

Dinner with Santa | Coconut Joe’s Bar & Grill

Thursday, December 18 

Art Bar: Create, Sip + Socialize | ArtFarm 

Midnight Madness | Downtown Annapolis 

Davy Dance Academy Presents the Elf on a Maryland Shelf Musical | Anne Arundel Community College (Dec. 18 & 19) 

Friday, December 19 

Day Off Discoveries | Annapolis Area Christian School (Dec. 19-31)

Annapolis Symphony Orchestra Presents Holiday Pops | Various Locations (Dec. 19-21)

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

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

Saturday, December 20 

A Sweet Time with Santa | Play Street Museum

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

A SQRRL! Holiday | Rams Head On Stage 

Honey Extraction Workshop | Homestead Gardens: Davidsonville

Breakfast With Santa | The Kentmorr Beach Bar and Grill

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

Watermark Presents the Special Historic Holiday Tour | 188 Main Street (Dec. 20-28)

Saturday, December 27 

Pressing Strings | Rams Head On Stage (Dec. 27 & 28)

Annapolis Toy Show | DoubleTree Annapolis

Military Bowl | Navy-Marine Corps Memorial Stadium

Monday, December 29

KPop Demon Hunters Jazz Dance Camp | Davy Dance Academy 

Creed—Creedmas | Live! Casino & Hotel

Tuesday, December 30 

Wicked at Christmas Dance Camp | Davy Dance Academy 

Frozen Ballet Camp | Davy Dance Academy 

Wednesday, December 31

New Year’s Eve Celebration | Federal House 

Watermark Presents the Family Friendly New Year’s Eve Cruise | 1 Prince George Street

‘80s New Year’s Eve Bash! with Doug Segree Band | O’Loughlin’s Restaurant

Slugs & Special Guests—New Year’s Eve | Dark Horse Annapolis

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Category: Arts & Entertainment, Community, Do Not MissTag: Activities, Annapolis, Family Friendly See all posts by Piper Langenfeld

About Piper Langenfeld

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We hope everyone has an amazing day watching the Blue Angels soar over Annapolis! 💙✈️ There’s truly nothing like this week in our city.

And once the planes clear, the fun keeps going 🎉 Our latest Do Not Miss List is packed with concerts, festivals, comedy, parades, ballet, cocktails, markets, and so much more happening all week long around Annapolis and beyond.

Check out the full list at the link in our bio + below and start planning your next adventure! 🔗

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