Annapolis kicks off the holiday season Sunday with the lighting of its Christmas tree in the center of the city.

Over the four weeks of December, the extravaganza unfolds to include theater, a chocolate festival, concerts, holiday markets, ballets, midnight shopping, quirk-fests like the Santa Speedo Run, and legendary events such as the floating lights parade and more.

Celebration of Hanukkah and Kwanzaa add to the general feeling of community. But it’s the Grand Illumination that makes Annapolis a perennial contender on national lists of the best Christmas towns.

“If you want the city to have a Christmas tree, if you want to engender the spirit of ‘Peace on Earth: Goodwill to men,’ meet the mayor at half past 8 o’clock in the Council Chamber. Let a large number of people turn out.”

That was the invitation that started it all in 1913, when Annapolis raised public funds for its first public tree, an idea adopted only a few years after electric Christmas lights became popular.

This season also marks 20 years since Zachary’s Jewelers, one of the key sponsors of the event, moved to the storefront overlooking Market Space after a devastating Main Street fire on the Friday night after Thanksgiving in 2005.

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Jeweler George Samaras supports a performance of “The Nutcracker” by the Chesapeake Ballet Company every year, and repeats his generosity on Sunday.

The entertainment starts at 3 p.m. and includes performances by the Annapolis Symphony Orchestra, the Edge Dance Complex, Naptown Sings and Plays and The Talent Machine Company.

Santa, Mrs. Claus and Elfie arrive aboard an Annapolis Fire Department truck to light the tree at 5:15 p.m.

Just for the record, that first illumination was a hit — with an asterisk.

The day after the lighting, city leaders admitted to the local newspaper that they mistakenly thought the lights were donated. So another call went out for contributions to raise $100 to pay the final purchase price — about $3,000 today.

Here are some other great things to do for the week ending Wednesday, Dec. 3.

Market and wine

11 a.m.-5 p.m. Friday

Great Frogs Winery hosts a Makers Market to start the holiday shopping season.

Vendors include Wild Raven Boutique, Katie Anne Jewelry, Mionee Body Butters and More, Amethyst and Opal Jewelry, My Fancy Finds Boutique, Take Care Vintage, Reyshi Designs, The Well-Infused Life Tea, Ephesians Coffee, and Quaintrelle Boutique.

The event also features tastings, plus wine and barrel sales. Admission to the market is free, although reservations for fee-based tastings are recommended.

I’m dreaming

8 p.m. Friday

Classic Theatre of Maryland launches its holiday season on stage with a longtime favorite, White Christmas.

The theatrical adaptation of the beloved 1954 Bing Crosby film features Irving Berlin’s music. The production runs through Dec. 29, with both weekend and weekday shows.

Tickets for adults are $61 to $95, plus taxes and fees. Discounts are available.

Military stories

10 a.m.-2 p.m. Saturday

Author Jennifer Barnhill will launch her new book, “The Military Stories You’ve Been Told and the Ones You Need to Hear,” at Old Fox Books.

“I wrote this book because one of my husband’s former bosses really pissed me off,” she wrote in her blog, “Military Dinner Table Conversations.”

The Arnold resident is a freelance military journalist and was named the 2025 Armed Forces Insurance Navy Spouse of the Year.

The book offers accounts of life inside the military community, told from the perspective of the families who live it.

A little art

Noon-4 p.m. Sunday

AND Creative is hosting a holiday show of miniature art by 14 talented artists.

During the opening reception at ArtFarm Studios, artists on display in the Tiny Art show will share the day with 10 local makers of gifts, crafts and other goods. The exhibit remains on display through Jan. 15.

Free admission.

A little Nutcracker

3-4 p.m. Tuesday

This time of year, it can feel like performances from “The Nutcracker” are everywhere, and libraries are no exception.

Dancers from The Ballet Theatre of Maryland will perform scenes from the famed ballet for children under 10 at Discoveries, the Anne Arundel County Public Library branch at Annapolis Mall.

Free.

Opening act

8 p.m. Wednesday

You could go to Rams Head on Stage for The Empty Pockets, the Chicago rock band that has been touring and recording since 2006.

Or you could turn out to catch the opening act, Daphne Eckman. The Annapolis singer-songwriter performs her own works about emotions.

Either way, the midweek show is $41-$63, plus taxes and fees.