Holiday Events

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The holiday season has arrived and our cozy coastal charm should be on your winter weekend bucket list! Consistently ranked one of the best cities in America during the holidays, Annapolis is a great place to spend the winter holiday enjoying time with family and soaking in the holiday spirit. Here's a list of holiday events to help plan your next getaway to Annapolis. 

An empty street at night with christmas lights hung up in front of the Maryland State House in

Midnight Madness

Don't miss Midnight Madness on Thursdays, December 7th and 14th, 2023, from 4:00 p.m. until Midnight and December 21st from 4:00 p.m. to 11:00 p.m., where select stores in downtown Annapolis along Main Street, Maryland Avenue, and West Street will remain open until midnight giving bargain-hunters and last-minute shoppers an excuse to get out and shop well into the night. The stores pull out all the stops with holiday displays, treats, special discounts, and sales for holiday shoppers. 

Parking Information


A light display with reindeer spelling out 'Lights on the Bay'

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 19th through January 1st. Weather permitting, the electric wonderland will be fully displayed 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 car.

If you visit Annapolis for the holidays, you will not want to miss this singular event. More than sixty animated and stationary displays dazzle onlookers, young and old. Driving through the park, you'll see a collection of Old Time Annapolis, a colonial village, and 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. 

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.

Christmas Tree Night Photo

Christmas Tree Lightings

Two different tree lightings kick off the holiday season in Annapolis. Join Annapolis Town Center for its annual event on November 19th, 2023, as visitors enjoy all-day entertainment, sidewalks overflowing with merchandise, Santa's workshop, hot chocolate on the Paseo, carriage rides, and so much more. 

The Grand Illumination of the Annapolis Tree will be held on November 26th, 2023, from 4:00 - 7:00 p.m., with a special visit from dancers, musical performances, and the big guy himself, Santa! With the most enormous tree yet, enjoy a display of ornaments and lights downtown at Annapolis' City Dock. Make it an evening with a historic pub crawl and shop the garland-lined streets of boutiques to find the perfect gift for loved ones. 


Annapolis Chocolate Binge Festival logo

Chocolate Binge Festival

This year's Chocolate Binge Festival returns to West Street on December 4th from 11 a.m. - 5 p.m. Shop for sweet and delectable treats, enjoy hot cocoa and coffee specialties, and a unique Gingerbread House display at the Visit Annapolis Visitor Center on West Street through December 11th. For details on the Gingerbread House Display or to participate, click HERE. Stay until 5 p.m. for the Grand Illumination of West Street and watch the holiday canopy of lights illuminate West Street from Church Circle to Madison Place! Learn more about the event and purchase tickets HERE.

Annapolis Holiday Market

Enjoy shopping in person from 50 artists in the open air December 7 - 10, 2023, along City Dock in downtown Annapolis. Enjoy Café dining and live entertainment to fill your afternoon before the holiday shopping season kicks into high gear!

Boat Filled with Christmas Lights at Night

Eastport Yacht Club Lights Parade

Magic happens on the water of the Annapolis Harbor on Saturday, December 9th, from 6 p.m. to 8 p.m., 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 along the waterfront at their favorite viewing spots to see this yearly spectacle and celebrate the holiday season. 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. Find many options to safely enjoy the annual lights parade on our event calendar.

Downtown Annapolis Lodging

Downtown Annapolis offers a wide array of accommodations, from nautically- and colonially-themed hotels to historic inns and bed and breakfasts.


Annapolis and Anne Arundel County offer a host of hotels, from historic colonials to modern luxuries, to satisfy all tastes and budgets. 

Inns & Bed & Breakfasts

Accommodation options abound in Annapolis and Anne Arundel County, but staying at one  their many inns or bed and breakfasts will guarantee a true taste of the region’s colonial past.

Vacation Rentals

Want to really live like a local? Vacation rentals run the gamut, from historic townhomes located right in downtown Annapolis to waterfront properties throughout Anne Arundel County. 


Plan Your Holiday Weekend in Annapolis!

Browse our full event calendar for a directory of holiday happenings. Start planning your stay at one of the area's hotels, a historic inn, or a B&B.


Holiday Event Parking 

Enjoy FREE holiday parking in downtown Annapolis this season at various locations. Additionally, eligible parking meters will be free for the first three hours for everyone between Thanksgiving and New Year's Day. A bonus free hour at the meters is available by using the code ParkDTA on the Parkmobile App. Visit Annapolis Parking for more information.