Voted one of the best towns for the holidays by Travel & Leisure, Annapolis is a must-see in December. The downtown streets of Annapolis are all gussied up with garland and lights, and just a stroll around town is enough to get you into the holiday spirit. At the 2nd Annual Chocolate Binge Festival on December 4th, sample all sorts of chocolate-and enjoy live entertainment-as you stroll the streets. But there's more. The Eastport Yacht Club Lights Parade, on the second Saturday of December at 6:00 p.m., draws a merry crowd to watch as dozens of beautifully decorated boats light up the Annapolis Harbor. Midnight Madness, on two consecutive Thursday evenings in December, brings out shoppers and revelers as the stores in downtown Annapolis stay open until Midnight. The excitement doesn't die down after Christmas. Football fans descend on the Navy-Marine Corps Memorial Stadium for an exciting college bowl game, the Military Bowl presented by Northrop Grumman on December 27. To cap off the year, the city of Annapolis also holds a fun, family-friendly New Year's Eve Celebration beginning at 3:00 p.m. on December 31st at City Dock and concluding with festive fireworks. 

Alley with Snowflakes during Midnight MadnessMidnight Madness Holiday Shopping
When: Thursday, December 1, 8, and 15; 6:00 p.m. to midnight
Where: Downtown Annapolis

Lights, garland, action! Historic Annapolis shops throw open their doors in a glorified block party that is open to all. Enjoy musical performances as well as food and refreshments at many stores as you stroll along Main StreetState Circle/Maryland Avenue, and the Arts District in search of that perfect gift. Explore the uniqueness that makes downtown Annapolis so appealing at this magical time of year. Presented by the Downtown Annapolis Partnership.

Chocolate Binge Festival
When: December 4, Noon - 5 p.m.
Where: First block of West Street in downtown Annapolis
Admission: $5.00 cash donations are greatly appreciated!

If you like chocolate, you won’t want to miss this festival featuring chocolate and holiday vendors galore! Specialty restaurant candy events include a chocolate fountain, candy apples, candy floss, “chocolate sushi”, and more. Enjoy live music, a marshmallow roast, an ugly sweater contest, as well as a moon bounce and other kids’ activities. The evening wraps up with a grand lever pull to illuminate the sky above the first block of West Street. Presented by the Annapolis Arts District and Inner West Street Association. Visit for more information.

Chocolate Binge Festival

First Folio! The Book that Gave Us Shakespeare
When: Thursday-Sunday, December 1-4
Where: St. John’s College, Elizabeth Myers Mitchell Gallery, 60 College Avenue, Annapolis
Admission: Free

The First Folio is the first complete collected edition of Shakespeare’s plays, published in 1623 seven years after his death. Compiled by two of Shakespeare’s fellow actors, it preserves 36 of Shakespeare’s plays. Without it, we would not have 18 of those plays, including “Macbeth,” “Julius Caesar,” “Twelfth Night,” “The Tempest,” and “Antony and Cleopatra.” Thanks to the First Folio, generations have experienced Shakespeare’s lasting influence on language, culture, theater, music, education, and more. There are 233 known copies in the world today. Eighty-two of the copies are held by the Folger Shakespeare Library. Visit for more information.

Lights on the Bay 
When: November 19 to January 1; 5:00 p.m. to 10:00 p.m. nightly, weather permitting
Where: Sandy Point State Park, 1100 East College Parkway, Annapolis
Admission: $15, car; $50, bus

Don't miss this spectacular drive-through holiday lights show beside the Chesapeake Bay. The event features more than 60 animated and stationary displays, including traditional Maryland-themed favorites, holiday and children’s displays. Proceeds benefit Anne Arundel Medical Center. Visit "Lights on the Bay" for more information.

Lights on the Bay

Holiday Candlelight Stroll
When: Fridays and Saturdays, December 2-3, 9, 16-17; 7:00 p.m. to 8:30 p.m.
Where: Tours depart from the Information Booth at City Dock, Annapolis
Admission: $21, adults; $12, children ages 3-11; children 2 and under, free

Learn about the origin of holiday traditions – including the significance of evergreens, Yule logs, Christmas trees and Santa Claus as you stroll through Annapolis with a festively attired guide. Includes a tour of the Hammond-Harwood House. Visit for more information.

Jolly Express Cruise
When: Weekends in December, including Christmas Eve, Christmas Day and New Year’s Eve 6:00 p.m., 7:00 p.m., and 8:00 p.m.
Where: Tours depart from the Information Booth at City Dock, Annapolis
Admission: $23, adults; $13, children under 12

Enjoy a 45-minute, holiday-inspired, “sleigh ride” cruise aboard the reindeer-bedecked Miss Anne. Cruise includes holiday music, hot cocoa, and Captain Santa at the helm. Visit for more information.

Annual Eastport Yacht Club Lights Parade
When: Saturday, December 10; 6:00 p.m. to 8:00 p.m.
Where: Annapolis Harbor and Spa Creek 
Admission: Free

Brightly decorated boats parade around the Annapolis waterfront in one of the City’s signature events. Thousands of lights and a host of jolly revelers make this a fun holiday event for the entire family. Prime viewing areas include:  Eastport, Spa Creek, City Dock and Naval Academy sea wall. Sponsored by the Eastport Yacht Club. Visit or Facebook for more information.

Eastport Yacht Club Parade of Lights

Parade of Lights Cruise
When: Saturday, December 10; 4:45 p.m. to 8:00 p.m.
Where: Begins and ends at the Severn Inn (1993 Baltimore Annapolis Blvd, Annapolis)
Admission: $145 includes dinner and a cruise

An Annapolis tradition. Enjoy dinner at Severn Inn followed by a dessert cruise aboard the luxurious Catherine Marie to watch the decorated boats cruising along Spa Creek in the Eastport Yacht Club Lights Parade. Visit for more information.

2016 Military Bowl
When: Tuesday, December 27; Starting at 3:30 p.m.
Where: Navy-Marine Corps Memorial Stadium (550 Taylor Avenue, Annapolis)
Tickets: 888-841-2787

The Military Bowl® presented by Northrop Grumman, benefiting the USO, will match a team from the Atlantic Coast Conference (ACC) against an opponent from the American Athletic Conference (AAC). Visit for more information.

Parachute into Navy-Marine Corps Memorial Stadium

City of Annapolis New Year’s Eve Celebration
When: Saturday, December 31
Where: Susan Campbell Park, City Dock, Annapolis
Admission: Free

Family activities fill the day and dancing fills the night. Traditionally, a first round of fireworks begins at 5:30 p.m. and the evening concludes with midnight fireworks. Visit for more information.