Annapolis Holiday events

Holiday events in Annapolis Today

Discover the best Holiday events in Annapolis! From festive Christmas markets to New Year's Eve fireworks displays & Holiday Bazaar, we have something for everyone. Explore the Annapolis's winter attractions and make lasting memories with friends and family. With so much to do in Annapolis, you'll never have a dull moment this holiday season.

|

Community Member

Community Member

Community Member

Join 232.1k+ Fellow Explorers

Holiday events in Annapolis Today

Holiday events in Annapolis Today

Wed, 03 Dec, 2025 - 06:00 PM

An Evening of Holiday Radiance

127 Lubrano Dr

Free

Explore events by date

calendar_icon

calendar_icon

calendar_icon

Custom Date

Pick Range

calendar_icon

Holiday events from nearby cities

Sun, 14 Dec • 12:00 PM

40th Annual Cookie Tour of Historic Homes

Union Square

38+ Interested

|

USD 25
Featured

Fri, 05 Dec Onwards

A Christmas Carol for Edgar Allan Poe

Motor House

16+ Interested

|

USD 50
Sat, 13 Dec • 12:00 PM

🌟 🎄 2nd Annual Holiday Craft Fair & Toy Drive! 🎁 🎅

iLove Events Center

5+ Interested

|

Free
Sat, 13 Dec • 08:00 PM

Holiday Improv Comedy Show - Falls Church, Virginia

The Center for Spiritual Enlightenment

Newly Added

|

USD 10
Fri, 19 Dec Onwards

'Twas the Night Before...CHAOS! Holiday Circus Spectacular

In the Dark Circus Arts

Newly Added

|

USD 37
Sat, 13 Dec • 12:00 PM

Canton’s Biggest Santa Bar Fest

1021 S Linwood Ave

USD 10
Sat, 13 Dec • 12:00 PM

The Worthington's Bad Santa Day Party

2900 O'Donnell St

Newly Added

|

USD 15
Sun, 14 Dec • 05:00 PM

Toys for Shelter Pets – Second Annual Christmas Charity Event

Hotel Hive

Newly Added

|

USD 15
Wed, 24 Dec • 09:00 PM

MATZOBALL® WASHINGTON DC XMAS EVE ages 21-49 December 24, 2025

Decades DC

Newly Added

|

USD 40

Explore Events around you

10 km

5 km

10 km

25 km

50 km

Loading events...

Annapolis's Most-Loved

Music events in Annapolis Today

Business events in Annapolis Today

Concert in Annapolis Today

Parties in Annapolis Today

Food & Drinks events in Annapolis Today

Crafts events in Annapolis Today

Festivals in Annapolis Today

Dance events in Annapolis Today

Health & Wellness events in Annapolis Today

All Categories

Frequently Asked Questions

Which kind of events are trending in Annapolis?

Here are the top trending events in Annapolis

All Events that you vibe with!

Customize your experience; only see the events that click with you!

Best in Annapolis, straight to your inbox

Never miss a single fun event; let us keep you updated!

Explore more in Annapolis

Holiday events from nearby cities