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 7, 14 from 6PM until Midnight and December 21 from 6PM to 11PM) 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.

Visit the Downtown Annapolis Partnership online for updates this holiday season. 

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 through a massive light show. This year marks the 20th anniversary of Lights on the Bay, held from mid-November 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 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.

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 3rd from noon to 5pm on the first blocks of West Street will be the 3rd 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 3rd 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 coco 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 ithroughout Annapolis for other unique gifts.

The entertainment starts off at noon on 2 different stages on West Street with a grand finale at 5pm 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 air stream camper.

Eastport Yacht Club Lights Parade

Magic happens on the water of the Annapolis Harbor on Saturday, December 9th,, from 6:00pm to 8:00pm, 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 2018 in Downtown Annapolis

Family activities fill the day and music and dancing fills the night at this annual celebration welcoming the New Year on December 31st. Kids’ activities will take place on Weems Whelan fields behind Maryland Hall and Bates Middle School. Participants are invited to park at Park Place garage and take City of Annapolis-provided shuttles to and from the new location. Activities will 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. Then, it’s off to area restaurants for dinner with the kids. The second round of festivities includes live music and dancing at Susan Campbell Park at City Dock beginning at 8:00 p.m. and ending with midnight fireworks.

Spots to View the Fireworks 

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

Holiday Event Parking