Holiday Events

Consistently ranked one of the best cities in America during the holidays, Annapolis is a great place to spend the weekend enjoying time with family and soaking in the holiday spirit.


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Consistently ranked one of the best cities in America during the holidays, Annapolis is a great place to spend the weekend enjoying time with family and soaking in the holiday spirit. Here's a list of holiday events to help plan your next holiday excursion in Annapolis. 

Midnight Madness

Don't miss Midnight Madness Thursdays, December 5 and 12 from 6:00 PM until Midnight and December 19 from 6:00 PM to 11:00 PM, where select stores in downtown Annapolis will remain open until midnight giving bargain-hunters and last-minute shoppers an excuse to get out and shop well into the night. It's also the perfect excuse to catch up with friends and take advantage of special deals in the middle of holiday fun with a Girls' Weekend. So, come enjoy the spirit of Annapolis as the town will be inundated with live music, holiday entertainment and cheer throughout the night.

Spectacular Holiday Light Display Comes to Sandy Point State Park

There's no better way to get the whole family into the holiday spirit than cruising along the shore of the Chesapeake Bay during Lights On The Bay,  November 24 through January 1. Weather permitting, the electric wonderland will be on full display nightly from 5:00 p.m. to 10:00 p.m. at Sandy Point State Park (1100 East College Parkway, Annapolis, MD 21409). Take a night - or a couple of nights - to enjoy the electric show from the warmth of your own car.

If you're visiting Annapolis for the holidays, you can't miss this once-a-year event. More than sixty animated and stationary displays dazzle onlookers young and old. Driving through the park, you'll see a display of Old Time Annapolis City, a colonial village, the North Pole, along with some regional staples like Midshipmen throwing their hats at graduation, the Thomas Point Shoal Lighthouse, and a Maryland Blue Crab; however, the most anticipated sight is the sixteen-foot teddy bear lighting up the Chesapeake Bay. Santa will also be visiting on Thanksgiving Day.

With all proceeds going to the SPCA of Anne Arundel County, you'll be treated to a spectacular show while contributing to a good cause.

Tree Lightings

Two separate tree lightings kick-off the holiday season in Annapolis. Experience the magic together during the Annapolis Towne Centre's annual Tree Lighting on November 23rd at 6:30 pm. Enjoy seasonal music, catch a glimpse of Santa, and grab a bite to eat as you sneak in a little holiday shopping before catching the spectacle with the whole family. Visit Annapolis Towne Centre online for more information.

Then, head to downtown Annapolis' City Dock for the Grand Illumination on December 1st from 5:30 pm to 7:00 pm. Santa arrives to help light the tree around 6:30 pm and help get everyone in the holiday spirit. The Jaycees serve hot chocolate and candy canes and have ornaments for children to decorate. The Jaycees also accept donations of unwrapped toys and non-perishable food items for their annual Angel Tree program, which helps local families in need during the holiday season.

Fire & Ice

Take some time away from the busy holiday season for the Annapolis Towne Centre’s Fire & Ice Festival on December 7, 2019, from 4-8 pm. Embrace the winter with smores over a cozy fire, live music, a light show, on-site vendors, cocktails, shopping, and tasty bites. Visit Annapolis Towne Centre online for more information.

Chocolate Binge Festival

Everyone loves chocolate and Annapolis' will be celebrating by filling West Street with local chocolate vendors ready to help chocoholics get through the holiday season. On Sunday, December 8th from noon to 5:00 PM on the first blocks of West Street will be the 5th annual Annapolis Chocolate Binge Festival, featuring family-friendly entertainment, chocolate, holiday shopping and the lighting of the West Street Holiday Light Canopy.

Start off the December holidays season with some fun and indulge your sweet tooth at the 5th annual Annapolis Chocolate Binge Festival, to benefit the Annapolis Arts District and We Care and Friends.  The day is loaded with family-friendly fun. There is a giant gingerbread house moon bounce for the kids, a giant snowball run where you can race your friends, you can roast marsh mellows and make smores at the fire pit in the middle of West Street with the Annapolis Fire Department, get a balloon animal, drink hot cocoa with the police department and visit Santa. Santa will be collecting toys, coats, and hats for the We Care and Friends Holiday Party for local kids in need.

You can also complete your holiday shopping at the holiday market at the Annapolis Chocolate Binge Festival featuring dozens of local craftspeople with a wide range of handmade items including jewelry, pottery, candles wood turnings, glass blowing and more. Plus visit the galleries and shops in the Annapolis Arts District and throughout Annapolis for other unique gifts.

The entertainment starts off at noon on two different stages on West Street with a grand finale at 5:00 PM with the grande illumination of the Holiday Light Canopy over West Street.

Admission is just a $5 suggested donation for adults (kids are free with parents). Everyone making a donation will get a complimentary hot chocolate from the airstream camper.

Eastport Yacht Club Lights Parade

Magic happens on the water of the Annapolis Harbor on Saturday, December 14th, from 6:00 PM to 8:00 PM, as boats suddenly appear out of the cold winter night illuminated with thousands of colored lights and crewed by jolly revelers.  Families and friends gather at their favorite viewing spots along the waterfront to see this yearly spectacle and to celebrate the holiday season together.  The Eastport Yacht Club Lights Parade is one of Annapolis’ signature events and we invite you to join us as a participant in the parade or as a spectator cheering on the decorated boats and their crews.  

Celebrate 2019 in Downtown Annapolis

The Annapolis New Year's Celebration kicks off with family-friendly activities and entertainment that will start behind Maryland Hall for the Creative Arts from 3:00 PM to 5:00 PM. There will be free activities for the kids including moon bounces, slides, obstacle courses, and crafts. Plus enjoy CrabTown Curbs Cuisine, food trucks, face painting and early family-friendly fireworks at 5:30 PM. Annapolis Parking for this event is at Park Place Annapolis and a free Circulator shuttle will bring you right to the event and back to Park Place Annapolis parking garage.

After the early fireworks stay in town and enjoy dinner with the family. There is a free Circulator bus starting at Park Place that will take you to any restaurant along inner West Street/Annapolis Arts District and Main Street.

Party on in Downtown Annapolis at City Dock 8:00 PM. There will be free live entertainment and dancing for all ages in the tent at Susan Campbell Park with a special close up fireworks display for the midnight countdown at the Annapolis City Dock and Harbor.

This event is sponsored and hosted by the City Of Annapolis

Spots to View the Fireworks 

  • Susan Campbell Park
  • Weems Whelan Fields behind Maryland Hall at 801 Chase Street, Annapolis, MD (early fireworks only)
  • Main Street
  • Spa Creek Bridge
  • Eastport
  • City Dock/Ego Alley
  • Aboard a boat in Annapolis Harbor

Holiday Event Parking