Downtown party time

4 p.m.-midnight Thursday

The first attempt to bring late-night holiday shopping to downtown Annapolis failed. Merchants were distressed by the defection of many customers to Parole Plaza, a shopping center built on Route 2 in the 1960s, and the then-brand-new Annapolis Mall.

Somebody had the great idea to anchor a month of late-night hours for stores around a parade on the second Saturday in December of 1988. The parade was a success. But “Annapolis After Hours” was a bust. No one showed up most nights and businesses dropped out. Shoppers who came downtown found stores closed.

Then someone suggested making it just one night, and Midnight Madness, part small-town holiday party and part shopping promotion, was born.

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Fast forward to 2023, and dozens of stores on Main Street, West Street, Maryland Avenue, State Circle, Market Space and Dock Street stay open late on the first three Thursdays of December. Music, food and decorations add to the fun of going downtown to shop instead of just getting what you want online.

Oh, and Parole Plaza has been replaced by Annapolis Towne Center, and the mall, now Westfield Annapolis, has several major anchor vacancies.

Still more shopping


This is the second year for the Annapolis Holiday Market, an event designed to keep people coming downtown for the holidays with the current popular shopping model, small craft shops.

The market is set up at 1 Dock St. and features 80 arts and crafts vendors, food and live entertainment over four days. It runs from 4 p.m. to 10 p.m. Thursday; 11 a.m. to 9 p.m. on Saturday and Sunday; and 11 a.m. to 5 p.m. on Monday.

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Uplifting voices

8 p.m. Friday

The Annapolis Chorale, the Annapolis Chamber Orchestra and the Chamber Chorus, all part of Live Arts Maryland, join guest pianist Mark Berman and vocalist Bernard Dotson at Maryland Hall on Dec. 8 for its annual Celebration of Christmas. $58 plus fees, with discounts for seniors, students and active military.

Oompa baby

3 p.m. Saturday

TubaChristmas — organizers spell it as one word — gives Annapolis area tuba and euphonium players a chance to perform holiday favorites with decorated instruments on the steps of St. Anne’s Episcopal Church. Plus, it’s a singalong. Free.


6-8 p.m. Saturday

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Nothing says holiday lights in Annapolis like the Eastport Yacht Club Lights Parade. This year, roughly 50 boats will be decorated — each with its own theme — and will parade around Annapolis Harbor on both sides of the Spa Creek Bridge and turn around in Ego Alley, the narrow channel at City Dock.

The event even has its own poster, this year designed by artist Barbara Brower. You can catch an online exhibit of poster entries and vote for the Maryland Federation of Art’s people’s choice award through Dec. 14. Free.

On Pointe

7 p.m. Saturday, 1 and 4:30 p.m. Sunday

Watch on YouTube

How do you describe the importance of “The Nutcracker?” to American culture? How many little girls and boys have taken ballet lessons so they could participate in an annual holiday production? How many children are enraptured by the Christmas Party, “Dance of the Sugar Plum Fairy” or the Mouse King?

There are plenty of youth dance academy productions this time of year, but there is only one show that combines the talents of resident dancers and students on Annapolis’ biggest stage. Ballet Theatre of Maryland’s production takes place over two weekends in Maryland Hall. $60 plus fees, with discounts for students, seniors and active military.

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The company also offers a Sugar Plum Fairy mixer with dancers for $10.

Christmas ante

7:30 p.m. Monday, Tuesday

Does it seem to you like there’s a Christmas Carol contest going on in Annapolis?

Colonial Players is presenting its popular adaptation of Charles Dickens’ “A Christmas Carol” this year, as is the Maryland Classic Theater. Maryland Classic is running a concurrent show, “White Christmas” — creating a holiday schedule full of performances for local theater fans.

Now Colonial Players has upped the ante with two appearances by Jefferson Mays, the Tony- and Obie Award-winning actor. Mays, who most recently appeared on Broadway as Mayor Shinn in the Hugh Jackman/Sutton Foster revival of “The Music Man,” will read the Dickens classic at Maryland Hall for the Creative Arts, then join “In Conversation With Jefferson Mays” the next night at Colonial Players Theater. $35-$45 plus fees for the reading. The Q&A is $35 plus fees.