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Arts & Entertainment, Christmas, Holiday

Holiday Events Happening this Week and Weekend

December 4, 2023 by Duffy Perkins
a lighted Rubber dinghy with snowman and santa waving
The Eastport Yacht Club Light Parade always has some wildly creative displays! Image courtesy of Eastport Yacht Club Lights Parade Facebook. 

Holiday Art Making

Christmas Canvas Class at Artsy Partsy

December 8, 6pm
December 9, 2pm

Your child can make a beautiful piece of art to either give as a gift, or treasure throughout the years.  Ages 8+. $22

Storytime & Craft with Author Lynn Roxy Gambrill at Park Books

December 9th,  11am – 12:00pm

Local author Lynn Roxy Gambrill reads her book Santa’s Visit to Maryland: A Parody of “T’was the Night Before Christmas” based on Maryland sights and scenes. Craft to follow storytime. Perfect for ages 3 and up. Free community event. 

A windowed door with a Christmas ball wreath
St. Michaels will be all decked out in holiday finery this weekend! Image courtesy of Christmas in St. Michaels Facebook.

Festive Pete the Cat Paint Class at Muse Paint Bar

December 10, 12-1:30pm

Kids will love working with artist-instructors to create a unique painting of the world’s least emotional cat. $35

Make a Holiday Evergreen Centerpiece at ArtFarm Annapolis

December 11, 6pm

Full of fruit, pods, and fresh flowers, nestling in a bed of aromatic greens, your centerpiece is 24″ long and overflowing with texture, color, and gold accents. You are free to bring pruners, but all other materials will be supplied. $50.

Markets

Holiday Jewelry Sale at the Annapolis Senior Center

December 4-8, 9:30am-3pm

Excellent gifts and personalized jewelry are a hallmark of this annual event that benefits the Center’s activities throughout the year. Free admission. 

A Santa statue sitting on a bench holding a candy cane outside
Old St. Nick is waiting to greet visitors in St. Michaels. Image courtesy of Christmas in St. Michaels Facebook.

Annapolis Holiday Market at Dock Street

December 7-10

The 80-vendor market will be filled with a wide range of art, crafts, food, and handmade gift items from local and regional art, craft, and food vendors. Free admission.

Midnight Madness in Downtown Annapolis

December 7, 4-11pm

Come visit downtown Annapolis (and Snowflake Alley!) Thursdays in December. Grab a hot cocoa and explore shops as they’re open late and merrier than ever.  

Wildberry Vintage Christmas Market

December 9, 2-6

An evening market with over 100 local small businesses, farm fresh eggs, unique gifts, and more! Free admission

Special Events

Eastport Yacht Club Lights Parade

December 9, 6-8pm

Magic happens on the water of the Annapolis Harbor as boats suddenly appear out of the cold winter night illuminated with thousands of colored lights and crewed by jolly revelers. 

Christmas in St. Michaels

December 8-9

Breakfast with Santa, a parade through the streets, a marketplace and sweet shop, a lighted boat parade, and much more make this an annual tradition over the decades. 

Specifically for Adults

Holly Jolly Hideaway at Annapolis Towne Center

December 7-10, evenings

Put on your silliest holiday pajamas and head on over to the Town Center for some yuletide fun. An adults-only holiday extravaganza! Free admission

Holly Jolly Hideaway in neon

Book Signing with Nancy Lawson at Old Fox Books
December 7, 7pm

Midnight Madness is happening all around you, but inside Old Fox Books and Coffeehouse on Maryland Ave, local author Nancy Lawson will be signing copies of her beautiful new book, Wildscape. A great event and gift for the gardeners and naturalists in your life. Free. 

Holiday Wine Pull and Fundraiser at Captain Avery Museum

December 8, 5:30-8:30

Live music, dancing, hors d’oeuvres, and a chance to come home with some really nice wine. $25 to attend, $20 for the wine pull.

Jay Fleming’s 9th Annual Holiday Party and Fundraiser for the Annapolis Maritime Museum

December 8, 6-9pm

The area’s favorite photographer holds this super fun party to benefit the Museum. Expect oysters from Tangier Sound, beer from Forward Brewing, rum drinks from Lyon Run, and much more. $25

Glistening in the Tree Paint and Sip at Muse Paint Bar

December 8, 3-5

It’s five o’clock somewhere! Artist instructors help you make a lovely festive piece of art while sipping and enjoying the holiday season. $25 (discounted price)

An Annapolis Christmas at Ram’s Head

December 11 and 12, 7pm

An Annapolis tradition, with local artists playing holiday favorites. 21+. $50

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Category: Arts & Entertainment, Christmas, HolidayTag: Annapolis, Christmas, events, Family Friendly, Holidays, St. Michaels See all posts by Duffy Perkins

About Duffy Perkins

Previous Post:SQRRL! several people on lit stage playing instruments and singing in Christmas costumes and a squirrelAnnapolis Moms Presents: SQRRL! Family Fun on December 23 at Rams Head
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❄️🏀 Winter Wo

❄️🏀 Winter Wonderland at Navy Basketball is back and it’s the perfect family day out! Enjoy cookie decorating, face painting, hot chocolate, holiday music, games, and so much more while cheering on Navy Men’s & Women’s Basketball in a festive doubleheader.

We love having Navy Athletics as one of our amazing Annapolis Moms community supporters, and this is such a great way to kick off the season with the kids. 🎄💙

Grab your tickets, bundle up, and make a day of it!

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Holiday Magic Awaits

Holiday Magic Awaits

This season, let Community Supporter Bayside Limousine sweep you and your loved ones into an unforgettable night of festive lights, laughter, and luxury. Relax in a chauffeur-driven limo, Sprinter, or party bus as you glide past 30+ dazzling holidays displays across the DMV — from the glowing shores of Lights on the Bay to magical park-drive-throughs. Skip traffic, parking, and stress — just cozy vibes, crisp night air, and glowing memories. Book now and make this holiday season sparkle.✨

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