For the second year in a row, Travel & Leisure has ranked Annapolis 15th on its annual list of the top 25 towns to visit for Christmas. The website, frankly, is late to the party.

Annapolis has been a Christmas town for a long, long time.

“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 1913 front-page notice in the local newspaper planted the roots of a community holiday in Annapolis, with a lighted tree in the public square when that idea was new.

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Thomas Edison’s business partner Edward H. Johnson had invented the first known set of lights for a tree about 30 years earlier, hand-wiring a set for his own home. By 1903, General Electric was selling them as expensive novelties for the rich — over $300 today — or renting them as a more affordable option.

Boston, New York and Hartford, Connecticut, all claim to have been the first city to have a lighted public tree for Christmas on Dec. 24, 1912, with the actual first declared by some writers to be a difference of flipping the switch 30 minutes apart.

A year later, Annapolis wanted a bright shiny tree, too. People contributed pennies and dollars, when that was real money. The excitement was so great that Mayor James F. Strange asked the newspaper to run another notice.

“Will the parents and old people please explain to the little people this Christmas tree is to contain no gifts. … It is the Christmas spirit that is wanted to be stirred by the Community Christmas Tree in everybody, but there are to be no gifts.”

And so it started. Every year, Annapolis develops that same old sugar plum fever, adding more to the winter holiday celebration.

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It’s impossible to take it all in during one season. So here, then, is an essential guide to the holidays in Annapolis.

Lights, please

This year's Eastport Yacht Club Lights Parade poster was created by artist Barbara Brower.
This year’s Eastport Yacht Club Lights Parade poster was created by artist Barbara Brower. (Courtesy of Eastport Yacht Club)

The original tree lighting continues Sunday with the Grand Illumination, this year with support from the city and several arts groups. It starts at 4 p.m. with music, dance and the arrival of Santa Claus escorted by firefighters.

There are plenty of other free light displays, including commercial displays like the one at Annapolis Town Center. The official Anne Arundel County tree lights up at 5:30 p.m. on Nov. 29 at the Glen Burnie Town Center.

If you need more or want to support a good cause, head to Sandy Point State Park through New Year’s Day for Lights on the Bay. The drive-through display raises funds for the SPCA of Anne Arundel County. Check the website for pricing.

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About 70 years after Annapolis lit its first tree, the Eastport neighborhood added its own twist. That’s when an informal parade of boats decorated with Christmas lights held by sailors became a regular event, the Eastport Yacht Club Lights Parade.

The festive parade is held from 6 to 8 p.m. on Dec. 9 in the Annapolis Harbor. 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.

Hanukkah begins on Dec. 7, and Chabad of Anne Arundel County lights a giant menorah at City Dock at 5:45 p.m. on Dec. 10. The lighting follows the annual Menorah Car Parade, a procession to the lighting starting at 5 p.m. at the Safeway on Housley Road and featuring cars illuminated by magnetized, lighted menorah.

The Banneker-Douglass Museum will hold its Kwanzaa lighting ceremony from 11 a.m. to 3 p.m. on the same day. It’s the opening reception for “A Story to Tell” exhibit of artwork by Maryland artist Ernest Shaw.


Annapolis has several holiday street festivals, including the Chocolate Binge Festival and the Artisan's market on inner West Street.
Annapolis has several holiday street festivals, including the Chocolate Binge Festival and an artisan market on inner West Street. (Rick Hutzell)

Recent years have seen growth in the number of festivals around Annapolis so that almost every part of the city has its own.

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None may be more popular than Midnight Madness, a late-night shopping festival in downtown that started in 1988. Businesses around Main Street, West Street, Maryland Avenue, State Circle, Market Space and Dock Street stay open late on the first three Thursdays of December, starting Dec. 4. Music, food and decorations all add to the fun of going downtown to shop instead of just getting what you want online.

Inner West Street, the first block beyond Church Circle, puts its own special take on the event on Dec. 14 with an artisan market starting at 5 p.m.

The Chocolate Binge Festival started in the 2010s as a way to extend the popular First Sunday Arts Festival on West Street into the holiday. It’s exactly what it sounds like. This year, the event is from 11 a.m. to 4 p.m. on Dec. 3, featuring all sorts of chocolate desserts and drinks. Admission is $5 plus fees, with a package of 15 tasting tickets costing $15.

This is the second year for the Annapolis Holiday Market. The event at 1 Dock St. features 80 arts and craft vendors, food and live entertainment over four days. It runs from 4 p.m. to 10 p.m. Dec. 7; 11 a.m. to 9 p.m. on Dec. 8 and 9; and then 11 a.m. to 5 p.m. on Dec. 10.

Other festivals include the Makers Market at Great Frongs Winery on Nov. 24, Quaker Holiday Market and the West Annapolis Holiday Market on Dec. 2, and the Annapolis Sons and Daughters of Italy Italian Christmas Market on Dec. 3.

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On stage

You cannot go wrong with holiday music, theater and dance. Even if you can do the “Dance of the Sugar Plum Fairy” in your sleep, it’s still worth a trip to see “The Nutcracker.”

The Classic Theatre of Maryland is staging two holiday productions this year: a stage version of Irving Berlin’s 1954 movie “White Christmas” from Nov. 24 through Dec. 24, and “A Christmas Carol” from Dec. 2 to Dec. 24. Colonial Players stages its version of “A Christmas Carol” starting Dec. 7. Ticket sales are in person only.

The Colonial Players stages "A Christmas Carol" musical over two weekends starting Dec. 7.
The Colonial Players are staging “A Christmas Carol” musical starting Dec. 7. (Courtesy of Colonial Players)

The Naval Academy Glee Club and the Annapolis Symphony Orchestra perform Handel’s “Messiah” in the academy chapel on Dec. 2 and Dec. 3. You can also hear the Annapolis Chorale and Chamber Chorus perform this holiday classic at St. Anne’s Episcopal Church on Dec. 15, 16 and 17.

Part of Live Arts Maryland, the chorale might be the busiest music group in Annapolis during the holidays. It joins the Annapolis Chamber Orchestra and guest artists at Maryland Hall on Dec. 8 for its annual Celebration of Christmas.

The Annapolis Symphony Orchestra will kick off “Holiday Harmony – 12 Musical Days of the ASO” on Dec. 14, with a new video of festive music released each day through Christmas Day on its streaming platform Symphony+. You can catch the ASO in person on Dec. 15 for the annual Holiday Pops concert.

If dance is more your thing, there are plenty of performances of “The Nutcracker” ballet.

The Ballet Theatre of Maryland has six performances at Maryland Hall in Annapolis starting Nov. 25, plus two more in Westminster and Hampstead.

For something a little less traditional, Annapolis has a lively music scene that’s especially true during the holidays. Check out the calendar at Rams Head On Stage. Its holiday acts in December include Christmas with the Celts on Dec. 4; the musical review “An Annapolis Christmas” by the nonprofit AMFM on Dec. 11 and 12; and “A SQRRL! Holiday,” an all-ages matinee, on Dec. 23.

And only in Annapolis

Some of what’s listed above is special to Annapolis, but you can probably find a lighted boat parade is some other waterfront city. And, late-night shopping isn’t all that unusual this time of year.

Nutcrackers and Ebenezer Scrooge are everywhere if you know where to look. But only in Annapolis? Here are the contenders for the truly unique.

Gov. Wes Moore and first lady Dawn Moore will welcome the public to Government House, the official residence, for the annual Holiday Open House from 10 a.m. to 1 p.m. on Dec. 9. Visitors will get to see the holiday decorations and enjoy punch and cookies.

The athletically inclined strip down to Speedos or other streamlined attire on Dec. 16 for a run around Maryland’s state capital starting at 12:15 from O’Brien’s Oyster Bar and Seafood Tavern on Main Street, a tradition dubbed the Santa Speedo Run. There is a fee to enter and enjoy the after-party, but spectating is free.

The Santa Speedo Run gives that athletically inclined another reason to run around Annapolis.
The Santa Speedo Run gives the athletically inclined another reason to run around Annapolis. (Bear Left / Flickr)

College football bowl games are a dime a dozen, but only the Military Bowl in Annapolis features a parade led by the Budweiser Clydesdales. You can get up close to the giant horses from 9 to 5 p.m. on Dec. 26 in West Annapolis, and enjoy music, food and shopping as part of a street festival. The parade starts at 10 a.m. on Dec. 27 at City Dock, following a route to Navy-Marine Corps Memorial Stadium, where there will be football.


Before you start dry January, there’s one final public party.

Annapolis stages two fireworks displays on New Year’s Eve. One for 7 p.m. is for children, while the midnight show is for adults. Both are over the harbor.

Whew. That’s a lot, and there’s more. Just keep your eye out for the event that suits your holiday style.

Now, does anyone know where I put those little wire hooks for the tree decorations?

Rick Hutzell is the Annapolis columnist for The Baltimore Banner. He writes about what's happening today, how we got here and where we're going next. The former editor of Capital Gazette, he led the newspaper to a Pulitzer Prize for coverage of the 2018 mass shooting in its newsroom.

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