Holiday Happenings in Annapolis

Annapolis is rated among the top U.S. cities to visit during the holidays. According to Travel and Leisure, it ranks 15th among their favorite places to celebrate. If you happen to be visiting this beautiful city for a winter fiesta here are some of the holiday happenings in Annapolis, Maryland.

Annapolis HalloWeekend Pub Crawl

Put on your best costume, bring your friends, and get ready for the downtown Annapolis pub crawl. Just register for your ticket ($13.66) and you’ll be able to participate in over 10 hours of Halloween pub-crawling. The event will be held on Saturday, October 28th, from 3pm-3am, and begins at Armadillos. Other bars on the crawl include Stan and Joes, McGarvey’s, Dock Street, ACME, and Fado’s Irish Pub.

Lights on the Bay

A family-friendly activity for the entire family, this takes place from November 22, 2017 – January 1, 2018, 5-10 p.m. at Sandy Point State Park. This is an annual drive-through Christmas light show sponsored by the Anne Arundel Medical Center. Drive along the shore of the Chesapeake Bay and see more than 60 animated and stationary displays illuminating the roadway. Cost is $15 per car. For information call (410) 481-3161.

Midnight Madness Holiday Shopping

Takes place the first three Thursdays in December: December 1st, 8th, and 15th, 2016, from 6 p.m.-midnight in downtown Annapolis, along Maryland Avenue, Main Street, and West Street. Historic Annapolis’ shops stay open late for this community block party. Everyone is welcome to come enjoy musical performances, food and refreshments and holiday cheer!

Annapolis Chocolate Binge Festival

Take advantage of the opportunity to eat chocolate all day long! On Sunday, December 4th from noon to 5 pm, join the party on West Street with local chocolate vendors ready to indulge your sweet tooth. There’s more to the festival than just chocolate, there’s loads of family fun! There is a giant gingerbread house moon bounce, a giant snowball, and a S’mores roast with the Annapolis Fire Department. In addition, Santa will be collecting toys and clothing for the We Care and Friends Holiday Party for local kids in need.

Eastport Yacht Club Lights Parade

Visitors and locals look forward to this annual event that will take place on Saturday, December 10th, from 6-8 p.m. This magical event happens on the waters of the Annapolis Harbor. Dozens of boats illuminated with thousands of colored lights and crewed by jolly revelers parade along the Annapolis Spa Creek Waterfront, extending from Primrose Road to the South and the USNA Seawall to the North.

Military Bowl and Parade

It all begins with a parade through Downtown Annapolis to the U.S. Navy-Marine Corps Memorial Stadium, featuring The Budweiser Clydesdale horses. Mark your calendars for December 28, 2017. 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) live on ESPN.

New Years Annapolis

Celebrate the coming New Year this December 31st at a family-oriented event at Susan Campbell Park and City Dock. Annapolis Children’s Museum starts the day with activities at 3 p.m. and commences with a family-friendly fireworks display at 5:30 p.m. The celebration continues with a night of entertainment, live music, and food in the Annapolis Harbor, and leads up to a countdown to the New Year and midnight fireworks. It’s free and everyone is welcome to join!

If you are visiting the area or a local stop into Festival Wine and Spirits to pick up a holiday libation to share. We have great bottles of wine to pair with interesting Farmer’s Market finds, or to give as a hostess gift. If you are heading to the military bowl, we have everything you need for a perfect tailgate. Our friendly staff is available to assist finding the perfect spirit for your holiday celebration.

*Updated on October 6th, 2017