Annapolis Holidays: A Dickens wonderland

When I visited Annapolis this summer, I fell hard for its charm and history. I knew I’d return one day — and I will. Next month, in fact. I’ll be taking the family to see this beautiful city all decked out in its holiday finest. Since I’m also a fan of Christmas decorations, I’m super-excited! Annapolis will be draped in greenery, lit with candles and glittering lights… OH, a perfect Dickens Christmas postcard in real life.

Maybe you’d like to visit too? Here’s a complete list of the Annapolis holiday events. See you there!

November: Annapolis holiday events

Lights on the Bay

Sandy Point State Park comes alive with a spectacular drive-through holiday light display on the shore of the Chesapeake Bay. This family favorite event features more than 60 brilliant displays, including Maryland-themed, holiday and children’s displays. All proceeds of this particular Annapolis holidays event benefit the Anne Arundel Medical Center.

• When: Tuesday, November 22 – Sunday, 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; mini-bus $30
• To learn more visit Lights on the Bay

Small Business Saturday

Shop small. Shop local. Small Business Saturday is the perfect day to support local business as you experience all the charm of walkable, downtown Annapolis. Get your holiday shopping done as you discover unique finds at Annapolis’ locally owned shops.

• When: Saturday, November 26, all day
• Where: Downtown Shops and Stores throughout Annapolis and the Chesapeake Bay 

Grand Illumination – City Tree Lighting

The annual Lighting of the Tree, Grand Illumination event kicks of the Christmas season with Santa and performances by area youth. The Annapolis Jaycees, event sponsor, will provide snacks and ornaments that kids can use to decorate the tree. Guests are encouraged to bring non-perishable food items and new, unwrapped toys to support the Angel Tree Project, an Annapolis holiday event that gives back!

• When: Sunday, November 27, 5:30 p.m. to 8:00 p.m.
• Where: Market Space at the Market House, 25 Market Street, Annapolis

December: Annapolis holiday events

Midnight Madness Holiday Shopping I and II

Shop till you drop at Historic Annapolis shops! Find the perfect gift and celebrate the season as you shop Main Street, Maryland Avenue, Inner West Street and State Circle! Outdoor musical performances will add to the festive experience.

• When: Thursday, December 1 and Thursday, December 8, 6:00 p.m. to midnight
• Where: Downtown Annapolis
• Admission: Free
• To learn more visit the Downtown Annapolis Partnership

Lights on the Bay

Sandy Point State Park comes alive with a spectacular drive-through holiday light display on the shore of the Chesapeake Bay. This family favorite event features more than 60 brilliant displays, including Maryland-themed, holiday and children’s displays. All proceeds of this event benefit the Anne Arundel Medical Center.

• When: Tuesday, November 22 – Sunday, 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; mini-bus $30
• To learn more visit Lights on the Bay

Holiday Candlelight Stroll

Discover the meaning of holiday traditions like evergreens, Yule logs, Christmas trees and Santa Claus as you stroll the festive streets of Annapolis and tour the Hammond-Harwood House with a Dickens inspired guide.

• When: Fridays and Saturdays, December 2-3, 9, 16-17 from 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
• To learn more visit Watermark Journey or call 410-268-7601

Jolly Express Cruise

When on the waterfront, sleigh rides take a festive turn — aboard the Miss Anne on the bay! Enjoy a “sleigh ride” with hot cocoa, holiday music and Captain Santa to guide the way.

• When: Weekends in December, including Christmas Eve, Christmas Day and New Year’s Eve at 6:00 p.m., 7:00 p.m., and 8:00 p.m.
• Where: Annapolis Harbor
• Admission: $23, adults; $13, children under 12
• To learn more visit Cruise on the Bay or call 410-268-7600

State House by Candlelight

The State House annual open house includes live performances by young musicians and 24 themed Christmas trees — one for each county in Maryland and the City of Baltimore. NOTE: This is a government building so photo ID is required for all guests age 16 or older.

• When: Saturday, December 3 from 6:00 p.m. to 9:00 p.m.
• Where: Maryland State House, State Circle, Annapolis
• Admission: Free
• To learn more visit the Maryland State House website

2nd Annual Chocolate Binge Festival

Chocolate lovers rejoice! Local chocolate vendors will be selling their specialities at this special holiday event. Head to the West Street Holiday Light Canopy area to enjoy live music, a marshmallow roast, holiday shopping, hot chocolate with the Annapolis Police Department and, of course, a visit with Santa. Presented by the Annapolis Arts District and Inner West Street Association, you can also bring toys and clothing to support kids in need.

• When: Sunday, December 4 from Noon to 5 p.m.
• Where: First blocks of West Street in downtown Annapolis
• Admission: $5.00 suggested cash donation
• To learn more visit Annapolis Chocolate Festival or call 443-452-7321

Children’s Holiday Tree Trimming Party

The Captain Avery Museum is welcoming the holidays with snacks, holiday crafts and fun. Satnat will be there, too, to visit with the kids.

• When: Sunday, December 4 from 1:00 p.m. to 4:00 p.m. Santa will be there from 1:00-2:30.
• Where: Captain Avery Museum, 1418 East West Shady Side Road, Shady Side
• Admission: Free
• To learn more visit Captain Avery Museum or call 410-867-4486

34th Annual Eastport Yacht Club Lights Parade

Head to the Annapolis waterfront to enjoy the annual light parade of boats. Sponsored by the Eastport Yacht Club, join in the festivities to see this spectacular display. Best viewing areas include Eastport, Spa Creek, City Dock and the Naval Academy Sea Wall. (Of all the Annapolis holiday events, this is my personal favorite!)

• When: Saturday, December 10 from 6:00 p.m. to 8:00 p.m.
• Where: Annapolis Harbor and Spa Creek
• Admission: Free
• To learn more visit Eastport Yacht Club online or the Eastport Yacht Club Lights Parade Facebook page.

11th Hour Holiday Shopping

Christmas shopping procrastinators unite! Come out to the shops on Main Street, Maryland Avenue, Inner West Street and State Circle to get that holiday shopping done. Shop will stay open late, and live musical performances and refreshments will be available. In the uniquely festive atmosphere of downtown Annapolis, shopping can be fun!

• When: Thursday, December 15 from 6:00 p.m. to 11:00 p.m.
• Where: Downtown Annapolis
• Admission: Free

2016 Military Bowl®

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). Don’t miss the parade either, led by the world-famous Budweiser Clydesdales!

• When: Tuesday, December 27. The parade begins at the City Dock at 10:30 a.m. Kickoff is at 3:30 p.m. 
• Where: U.S. Navy-Marine Corps Memorial Stadium, 550 Taylor Avenue, Annapolis
• Admission: Varies by event. Check the website for details of all events and for vacation packages.
• To learn more visit the Military Bowl website. Call 888-841-2787 for ticket availability.

City of Annapolis New Year’s Eve Celebration

Wrap up the year at the annual Annapolis New Year’s Eve Celebration. Family activities begin at 3:00 p.m. and include face painting, an obstacle course, moon bounce and live music. The kids’ celebration ends with a fireworks display at 5:30 p.m. The adult celebration begins at 8:00 p.m. and ends with fireworks as the new year arrives.

• When: Saturday, December 31 from 3:00 p.m. to 6:00 p.m. for families; 8:00 p.m. to midnight for adults
• Where: Ball Fields behind Maryland Hall, 801 Chase Street, Annapolis for families; Susan Campbell Park, City Dock, Annapolis for adults
• Admission: Free
• To learn more, including parking and shuttle information, visit the City of Annapolis website or call 410-263-7997

For more information on all the Annapolis holiday events plus other activities happening in Annapolis, or for lodging and vacation packages, head over to Visit Annapolis & Anne Arundel County.