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 4th Annual Chocolate Binge Festival on December 2nd, 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 three consecutive Thursday evenings in December, brings out shoppers and revelers as the stores in downtown Annapolis stay open until Midnight or 11:00 p.m.. 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 31 at 12:00 p.m. 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.
Midnight Madness Holiday Shopping
When: Thursdays, December 6 and 13; 6:00 p.m. to 12:00 p.m. December 20; 6:00 p.m. to 11:00 p.m.
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 Street, State 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.
State House by Candlelight
When: December 1, 5:00 - 9:00 p.m.
Where: Maryland State House
Enjoy this annual open house featuring performance by young musicians and vocalists from throughout Maryland. The oldest State House in continuous legislative use in the nation will be adorned with 24 christmas trees representing every Maryland county and Baltimore City. Photo identification is required for individuals age 16 and older.
Illuminated London Town
When:Fridays & Saturdays, December 7-22, 6:00 - 9:00 p.m.
Where: Historic London Town & Gardens
Experience the magic of a winter evening at Illuminated London Town! Sip hot cider and roast s'mores beside roaring fires in the Historic Area. Explore the gardens illuminated with festive holiday lights. Discover colonial nighttime festivities and holidays at candlelit William Brown House, decorated for the season. Enjoy special performances in the gardens each week.
Chocolate Binge Festival
When: December 2, 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 www.annapolischocolatefestival.com for more information.
Lights on the Bay
When: November 17 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 the SPCA of Anne Arundel County. Visit "Lights on the Bay" for more information.
Holiday Candlelight Stroll
When: Fridays and Saturdays, December 1-2, 9, 15-16; 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 www.watermarkjourney.com for more information.
Jolly Express Cruise
When: Fridays-Sundays, December 1-31 (except Saturday, December 8); 6:00 p.m., 7:00 p.m., 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 www.cruisesonthebay.com for more information.
Annual Eastport Yacht Club Lights Parade
When: Saturday, December 8; 6:00 p.m. to 8:00 p.m.
Where: Annapolis Harbor and Spa Creek
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 the Eastport Lights Parade or Facebook for more information.
Parade of Lights Cruise
When: Saturday, December 8; 4:45 p.m. to 8:00 p.m.
Where: Begins and ends at the Severn Inn (1993 Baltimore Annapolis Blvd, Annapolis)
Admission: $145 (All Inclusive)
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 www.watermarkjourney.com for more information.
2018 Military Bowl
When: Monday, December 31; Starting at 12:00 p.m.
Where: Navy-Marine Corps Memorial Stadium (550 Taylor Avenue, Annapolis)
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 www.militarybowl.org for more information.
City of Annapolis New Year’s Eve Celebration
When: Monday, December 31, 3:00 p.m. to 5:15 p.m. kid-friendly activities; 8:00 p.m. to midnight for all
Where: Weems Whelan Fields behind Maryland Hall, 801 Chase Street, Annapolis and Susan Campbell Park, City Dock, Annapolis
Family activities fill the day and music and dancing fills the night at this annual celebration welcoming the New Year. For the second year, 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.
Discover additional lodging options located just 30 minutes from Annapolis and 10 minutes to Baltimore, check out TheHotelsAtBWI.com.