Holiday Events
Midnight Madness
Don't miss Midnight Madness on the first two Thursdays of December from 4:00 p.m. until Midnight and the third Thursday 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.
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. Weather permitting, the electric wonderland will be fully displayed nightly. 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 Lightings
Two different tree lightings kick off the holiday season in Annapolis. Join Annapolis Town Center for its annual event in November 2024, 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 the first Sunday in December, 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.
Chocolate Binge Festival
The Chocolate Binge Festival returns to West Street on the first Sunday of December. 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 along City Dock in downtown Annapolis in December. Enjoy Café dining and live entertainment to fill your afternoon before the holiday shopping season kicks into high gear!
Eastport Yacht Club Lights Parade
Magic happens on the water of the Annapolis Harbor on the second Saturday of December, 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.
Hotels
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.
