It's the most wonderful time of the year! And we've got your ultimate guide for all things Christmas and holiday fun in Annapolis to make help make your holidays the best with your family.
Big thanks go to our local businesses and organizations that are hosting these fantastic community events. Many are free and low cost.
From our MacKID families to yours, we wish you the most joyous holiday season!
We'll continue to add Christmas and other holiday events to this guide as we hear of them.
Please check back often for the most-up-to-date calendar of events!
Thank you to Cottonwood for making this guide possible!
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Cottonwood is your new favorite place for all things sewing, crafting, antiques and vintage items, gifts, jewelry, clothing and more! We offer a wide range of classes and get togethers!
Take advantage of our maker’s space and classroom. Get advice on projects from our knowledgeable staff. Learn about our epic sewing machines: from beginner entry-level machines, embroidery, domestic, longarms up to industrial machines by Bernina, Juki, and bernette.
Stop by today to see what the buzz is about!
Link to sites: https://cottonwoodinthepark.com/
Social media pages: Instagram | Facebook
Address: 548 Benfield Road Severna Park, MD 21146
Phone: 443-288-0884
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🎅🏽 Santa Sightings
Thru December 24
Santapolis: A Magical Holiday Experience (Picture Opp- Registration required)
Thru December 31
Weekends Thru December 21
Photos with Santa @ Homestead Gardens
December 6
Winter Wonderland at Douglas Realty - Elvaton Park Office
December 12 - 14
The Magic of Christmas at Anne Arundel Fairgrounds
December 21
Breakfast with Santa & the Grinch (Plus Holiday Meal kits)
🎄 Christmas Tree Lightings
Downtown Annapolis Tree Lighting - Grand Illumination Event
✨ Light Displays
Thru January 1
Lights on the Bay MD- Drive Thru Display
December 13
43rd Annual EYC Lights Parade!
Thru February 28
🛍️ Holiday Markets
Thru December 21
Sleigh Bells Ring HERE - a pop-up shop
November 29
Shop Small Saturday at Wildberry Field Market
December 7
Italian Christmas Market- Annapolis
December 11 & 18
Midnight Madness and Holiday Market on West Street
December 18-21
🎁 Charitable Giving Opportunities
Thru November 30
Share the Warmth @ Annapolis Mall
Thru December 15
Salvation Army Angel Trees (Community-Focused Giving)
December 18
Ugly Sweater & Holiday Toy & Food Drive at The Lodge Annapolis
🚶 Unique Annapolis Tours
Thru December 31
Fridays, Saturdays & Mondays Thru December 22
Holiday Traditions Tour at William Paca House
Fridays & Saturdays Thru December 27
Weekends Thru December 28
Colonial Annapolis & Maryland State House Walking Tour
🎤 Unique Annapolis Performances (various dates)
November 30
The Nutcracker at Zachary’s Jewelers
December 5
December 7 & 14
Tea and Ballet with the Sugar Plum Fairy and Nutcracker Prince
December 7 & 16
The Bay Winds Band Winter Concert
December 13, 14, 20 & 21
December 18
Elf on a Maryland Shelf Musical
December 19
A Merry Mix-Up (Various times)
Elf on a Maryland Shelf Musical
White Christmas (times vary by date)
December 20
A Merry Mix-Up (Various times)
White Christmas (times vary by date)
December 21
A Merry Mix-Up (Various times)
White Christmas (times vary by date)
December 22
A Merry Mix-Up (Various times)
White Christmas (times vary by date)
December 23
A Merry Mix-Up (Various times)
A Fright before Christmas – Ghost story dinner at Middleton Tavern
White Christmas (times vary by date)
December 24
White Christmas (times vary by date)
❄️ Other Holiday Events
Thru December 19
Great Annapolis Gingerbread Houses
Thru December 24
Homestead Gardens’ Train Display
November 29
Small Business Saturday in Downtown Annapolis
November 30
Circus Pop the Holiday Bubble-bration
December 6
Winter Wonderland at Douglas Realty - Elvaton Park Office
December 7
Annapolis Chocolate Binge Festival
December 12 - 14
The Magic of Christmas at Anne Arundel Fairgrounds
December 18
Ugly Sweater & Holiday Toy & Food Drive at The Lodge Annapolis
Early Bird (9:30am) and Late Night (5:00pm) Bingo
December 19
Cookies & Story Tale with the Grinch and Elves
December 20
Merry Grinchmas at Main Street
London Town by Candlelight: Family Hours
Jolly Jingle Pj Jam at My Gym Annapolis
December 21
Winter Solstice Celebration at Wellsview Cottage
Did we miss any Christmas or holiday events in Annapolis and surrounding communities?
Please submit them HERE, and we'll get them added to the calendar and this guide right away!
