The holiday season is upon Annapolis. You could catch a production of the musical “White Christmas,” shop at the first of several holiday markets or enjoy the century-old tradition of the Annapolis tree lighting. Those are some of the best things to do starting the day after Thanksgiving through Nov. 29.

Hidden holiday

6 p.m. Friday

Annapolis Town Center has set up the Holly Jolly Hideaway, a cocktail lounge near Santa’s Cottage. The 21-and-over space is open Thursday-Sunday until 11 p.m. through Dec. 23. Each weekend has a different theme, with fancy attire this weekend, and a “Carol-oke” singalong from 7-9 p.m. Sunday. Free admission.

The markets open

11 a.m.-4 p.m. Friday

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Great Frogs Winery kicks off the holiday market season in Annapolis with its Makers Market Black Friday Event, featuring 12 local vendors plus engraved bottles of the only wine grown in Annapolis. Singer-songwriter Madisun Bailey will perform from 2:30-5 p.m. Free admission.

Santa at the helm

2 p.m. Friday

Watermark Cruises is the company behind the Harbor Queen cruises and water taxis, but starting the day after Thanksgiving, it will offer 45-minute tours of the Annapolis Harbor aboard the Jolly Express. Multiple trips are scheduled Thursdays through Sundays until Dec. 31. The trip includes hot cocoa, music, blankets and is piloted by a captain dressed as Santa. $25 for adults, $13 for children under 12.

‘I’m dreaming of a …’

8 p.m. Friday

The Classic Theatre of Maryland premieres the first of its holiday productions, a stage version of the 1954 movie musical “White Christmas.” Weekend performances continue at 2 p.m. and 8 p.m. Saturdays and 2 p.m. Sundays through Dec. 24. $55-$75 plus fees, with discounts for seniors and young professionals.

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Shop the arts

11 a.m.-4 p.m. Sunday

There’s Plaid Thursday, Black Friday, Small Business Saturday and now Artists Sunday. Participating galleries around Annapolis will have various shows and receptions. One to check out is ArtFarm, where the Artists Sunday Market and Gallery Reception will be held in the new big studio. Seventeen painters, craftsmen, authors and designers will display and sell their work. Free admission.

Light that tree

4 p.m. Sunday

The Annapolis Grand Illumination takes place next to the Market House, featuring dancing and caroling by local arts groups leading up to the lighting of the city Christmas tree. This year’s tree decorations are designed by local kids. Free

Annapolis will light its tree Sunday, Nov. 26 in the Grand Illumination. It's a tradition stretching back more than a century.
Annapolis will light its tree Sunday, Nov. 26 in the ‘Grand Illumination.’ It’s a tradition stretching back more than a century. (Rick Hutzell)

Yuletide traditions

11 a.m. Monday

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Historic Annapolis celebrates early American holiday traditions with a candlelight tour of the William Paca House, home to one of Maryland’s signers of the Declaration of Independence. The one-hour event explores how the Paca household prepared for their holiday guests. Space is limited, and the Saturday tour was already sold out. $15 general admission, with discounts for Historic Annapolis members and volunteers, members of the military and children under 17.