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Holiday Season in Annapolis

November 27, 2017 by Rachel Gontkovic

Photo of decorations adorning downtown businesses during the holiday season in Annapolis
Photo credit annapolis.com

The holiday season in Annapolis is always such a magical and unique time of the year. When the huge tree in downtown Annapolis is lit right after Thanksgiving, you know that the holidays are here. Below are a few of my favorite events to attend in Annapolis during the month of December, along with a few insider tips to make this season great!

MIDNIGHT MADNESS

Beginning Thursday, Dec. 7th and running for three consecutive Thursdays is Midnight Madness which is not to be missed!  All of the shops in downtown Annapolis stay open until midnight and some offer great specials, food and drinks!  It’s a great excuse to spend time with your family and friends and enjoy live music and entertainment as well!

One of my favorite places to stop and shop along the way is Capital Teas. They provide samples of their seasonal tea to enjoy and last year, I purchased a chocolate tea that was truly amazing! Also, Local By Design is a great place to shop in downtown Annapolis.  During Midnight Madness, they provide wine while you shop the work of local artists, most of whom offer Chesapeake Bay inspired artwork, jewelry, home goods and clothing.  ​

​LIGHTS ON THE BAY​

The entire family will love the fabulous light display at Sandy Point State Park {link to website}! Hop into the car and make your way through the many light displays depicting the Chesapeake Bay Area. This year marks the 20th anniversary of Lights on the Bay, held from mid-November through January 1, 5-10 PM.  All of the proceeds benefit the SPCA of Anne Arundel County. My kids loved going to see the Lights on the Bay  when they were little. We would tour the lights and then go home and have hot chocolate!

CHOCOLATE BINGE FESTIVAL

Who doesn’t LOVE chocolate – especially during the holidays?! Don’t miss the second annual Chocolate Binge Festival {link to website} on Sunday, December 3rd from noon to 5pm held the first blocks of West Street. This family friendly event features entertainment, includig a gingerbread moon bounce and snowball race, hot chocolate, s’mores,  holiday shopping, a visit with Santa, and the lighting of the newly expanded West Street Holiday Light Canopy. The event benefits the Annapolis Arts District and We Care and Friends.

EASTPORT YACHT CLUB LIGHTS PARADE

Photo of yacht decorated for the annual Annapolis parade of lights - a popular event during the holiday season in Annapolis
Photo credit visitannapolis.org

One of the most anticipated annual events of the holiday season in Annapolis is The Eastport Yacht Club Lights Parade. In 2016, this event won the Best Holiday Parade in the USA Today 10 Best Readers’ Choice Contest, and it’s nominated again this year! 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. We always like to enjoy the parade from the Spa Creek Bridge, but viewing is great at City Dock too. The lights parade will be in the Annapolis Harbor on Saturday, December 9th, from 6:00pm to 8:00pm!

CELEBRATE 2018 IN DOWNTOWN ANNAPOLIS

End the holiday season in Annapolis on a high note! Have a blast this New Year’s and celebrate downtown on December 31st. For the second year, kids’ activities will take place on Weems Whelan fields behind Maryland Hall and Bates Middle School. Activities include face painting, an obstacle course, moon bounces and music performed by kids’ rock bands. The first round of festivities wraps up with on-site fireworks at approximately 5:30 p.m. After fireworks, my kids and I will head out to dinner at Joss or Nano for sushi. (My kids love sushi!) After dinner around 8:00pm, we’ll head downtown to Susan Campbell Park for the second round of festivities that includes live music and dancing at Susan Campbell Park in City Dock. At midnight, we’ll ring in the New Year with fireworks again! Such a great way to spend New Year’s Eve!

These are just a few of my favorite ways to celebrate the holiday season in Annapolis, but there are so many more, like the Hanging of the Greens by the Jacyees, the Holiday Shop at Homestead Gardens in Davidsonville (complete with an amazing toy train and hundreds of decorated trees), and the Holiday Candlelight Tours. And, probably the best thing of all is that metered parking in downtown Annapolis is FREE for the entire month of December! So don’t miss this amazing town during the holiday season, another great way to enjoy the Annapolis lifestyle.

Hope to see you at one of these great events!

Filed Under: Annapolis Lifestyle Tagged With: annapolis, annapolis events, annapolis homes, annapolis lifestyle, annapolis living, annapolis real estate, annapolis realtor, annapolis shopping, downtown annapolis, holidays in annapolis, rachel frentsos, real estate agent, realtor

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