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Free or Cheap Things to Do With Kids Over Winter Break in Annapolis

December 14, 2025 by Ricky Hartford
Noon Year's Eve Celebration

Winter break is magical… for about 24 hours. After that, the snacks are gone, the screens are glowing, and someone is already bored. If you’re looking for budget-friendly ways to get out of the house, Annapolis has plenty of free and low-cost options to keep kids busy (and parents sane).

Visit the Library (It’s More Than Books)

Several Anne Arundel County Public Library branches near Annapolis offer free programs during winter break:

  • Busch Annapolis Library – Teen hangouts, decorate wrapping paper, and noon year’s eve celebration.
  • Discoveries: The Library at the Mall – Storytime, crafting, and noon year’s eve celebration.

Check the library’s online calendar before you go! Many events don’t require registration and work well for last-minute plans.

Bundle Up and Hit the Trails

Cold weather doesn’t mean staying inside. Quiet Waters Park, Broadneck Park, and Kinder Farm Park are great for winter walks, bike rides, and playground time, without the crowds of warmer months.

Explore Downtown Annapolis on Foot

Turn downtown into an easy adventure: walk City Dock, count boats in the harbor, window shop on Main Street, or grab hot chocolate and people-watch. It feels festive without requiring a plan or a budget.

Visit Free Museums and Landmarks (or Free Museum Days)

These local spots offer free admission year-round or on select days:

  • Banneker-Douglass-Tubman Museum – Always free. This museum will be closed from December 25 to January 1.
  • U.S. Naval Academy Museum – Free admission (valid ID required for base access)
  • Maryland State House – Free to enter during open hours
  • Waterfront Warehouse – Part of Historic Annapolis, take a quick visit inside one of Annapolis’ oldest extant warehouses.

Even a short visit can feel like a big outing for kids.

Head to Annapolis Mall for a Cold-Weather Outing

When it’s too cold (or too wet) to be outside, Annapolis Mall offers several free options:

  • Window-shopping games like scavenger hunts or “design your dream outfit”
  • Be with Me Playseum is open for $15 a ticket. If you bring 15 used or new children’s books, you will get a free admission. You can declutter your house and play for free!
  • LEGO® Store has play tables that you can stop in and use for a quick play break.
  • SPCA’s Paws at the Mall allows you to meet some furry friends.
  • Today at Apple sessions at the Apple Store (free, but check availability).
  • Seasonal decorations and displays that still feel special without spending money

It’s warm, easy, and surprisingly effective for breaking up long winter days.


Winter break doesn’t have to mean expensive trips or packed schedules. With a few free programs, outdoor breaks, and easy local outings, you can keep kids busy—and still enjoy the downtime.

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Category: CommunityTag: Family Friendly, kids activities, winter break See all posts by Ricky Hartford

About Ricky Hartford

Ricky Hartford is fueled by cold brew, Celtics highlights, pop culture, and a perfectly placed Oxford comma. By day, he works in marketing and communications at Anne Arundel Community College, where he helps shape the college’s voice through content and storytelling. With over a decade of experience and a Master of Science in Strategic Communications, he’s helped nonprofits and local publications sound sharper, look better, and connect more clearly with their audiences. When he’s not working, he’s probably at the movies, on the basketball court, planning his next vacation, or convincing someone (anyone) to talk about the latest trashy reality show. Annapolis is his happy place, especially if it involves a drink downtown and hanging out by the water.

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🎭 Our amazing Annapolis Moms Community Supporter, The Talent Machine Company, is bringing the mystery, music, and fun to the stage this summer!

The reviews are in, and The Talent Machine’s production of Curtains is "pure entertainment...with a wonderfully talented teenage cast. Audiences are sure to walk away with a renewed appreciation for the magic of musicals." See for yourself! Four shows left of Curtains: A Musical Comedy Whodunit: July 16, 17, 18 & 19. Tickets just $20. Don't miss the mystery, the mayhem, the music -- and the incredible dancing!

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🚨 SAVE THE DATE: The Puppy Plunge is BACK! 🐾💦

Our incredible friends and community supporters at the SPCA of Anne Arundel County 🐶 are bringing back one of the absolute best dog-friendly events of the summer, and we couldn't be more excited to support them! 🎉

Mark your calendars for Sunday, August 23, 2026 📅 and get ready for a day of sandy paws, happy splashes, and community fun—all for a fantastic cause. 🌊🐕

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🎒 What to bring: Your four-legged best friend, beach chairs, blankets, and sunscreen! 🐕🦺🏖️☀️

More details on food vendors, sponsors, and entertainment are coming soon, so keep an eye out for updates. 📢 Let’s pack the beach and show our support for our local shelter animals! 🌊🐕

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