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  • Mid-Atlantic Events Magazine

Holiday Adventures begin in Annapolis & Anne Arundel County

Winter in Annapolis brings a mystical charm to our historic, brick-laden streets. Consistently ranked as a Top Christmas destination year after year by Travel + Leisure, and with the Best Holiday Lights Display in Maryland at Lights on the Bay at Sandy Point State Park, Annapolis is the perfect holiday town for a winter escape. Explore holiday markets and winter festivals; go ice skating outdoors; wander the historic district and wonder at the holiday lights and 18th-century architecture; or shop at Arundel Mills for the perfect holiday gift! There's all this and so much more to discover in Annapolis & Anne Arundel County- Where Winter Adventure Begins!

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November 4 Tug of War (Annapolis vs. Eastport) Once again, the Maritime Republic of Eastport has declared war on the City of Annapolis, its colonial overlord on the "mainland." The just-for-fun annual smackdown continues this year on Saturday, November 4, when the two villages work out their differences in an annual Tug-of-War billed as the Slaughter Across the Water. Come for the Tug, pick a side, and enjoy live music, great competition, food, and adult beverages. This event is free and open to the public.

November 3-5 & November 10-12 Annapolis Jazz & Roots Festival (Eastport) The Annapolis Jazz & Roots Festival will be spread over the first two weekends of November in Historic Eastport. Enjoy New Orleans Jazz at the Peerless Rens or a lecture at the Eastport-Annapolis Neck Library. St. Luke's Episcopal Church and Eastport United Methodist Church will also act as concert venues for the festival. Stay in historic downtown Annapolis or book a local short-term rental for two weekends of culture, history, jazz, and live music!

November 10 Veterans Classic Basketball Tournament (Naval Academy) Join basketball fans in Alumni Hall on Friday, November 10, 2023, for the 10th Annual Veterans Classic. This men's basketball event honors veterans of all service branches. At 6 p.m., Duquesne will take on the College of Charleston. At 8:30 p.m., the Midshipmen will face the Temple Owls. Tickets are good for both games!

November 11 Living History on Pinkney Street: His Majesty's Marines (Annapolis) Come chat with the King's Marines to learn about their unique branch of service as sea soldiers of the King, their uniforms, and weapons they carry. A special talk, “Conversations with the Captain,” will be presented at 11:30 am and 2:30 pm. Families and those Loyal to the King are welcome. But be careful – they may try to recruit you to serve! Suggested Donation: $5

November 12 Chesapeake Bay Bridge Run/Walk (Anne Arundel County) The Chesapeake Bay Bridge Run is a 10K race that traverses the eastbound span of the Chesapeake Bay Bridge from Anne Arundel County to Kent Island in Queen Anne's County and finishes with a huge post-race party! Once a year, the bridge shuts down traffic for a race that tests your mettle and perhaps your fear of heights! The views and photo ops abound, and this race is bringing in race enthusiasts from across the country.

November 19 - January 1 Lights on the Bay (Sandy Point State Park) There's no better way to get the whole family into the holiday spirit than cruising along the shores of the Chesapeake Bay during Lights on The Bay, November 19, 2023, through January 1, 2024. Weather permitting, the electric wonderland will be on full display nightly from 5:00 p.m. to 10:00 p.m. at Sandy Point State Park. Take a night - or a couple of nights - to enjoy the electric show from the warmth of your car. There is even a special night to walk to display with your pup! Details on their website.

November 26 Grand Illumination (Annapolis) The Grand Illumination and annual tree lighting occur near the Market House every year on the Sunday after Thanksgiving. The celebration begins at 4:30 p.m. with dancing, carols by local school groups, and a special visit from Santa and Elfie! Make this Annapolis Holiday event a part of your family's traditions! 4:30 p.m. – 7:00 p.m.

November - December Jolly Express Cruise (Annapolis) Ho, Ho, Ho, and a Bottle of Rum! Well, not the rum, but Santa returns to the shores of Annapolis on his Jolly Express Cruise this holiday season! Grab the kids and family and start a new holiday tradition! Miss Anne will be adorned with festive reindeer spirit for an intimate 45-minute "sleigh ride," including hot cocoa, holiday music, and good cheer. Bring your blankets to stay cozy and warm. Cruises are available on select dates throughout December.


December 3 Annapolis Chocolate Binge Festival (Annapolis) 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 10th. 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!

December 7, 14 & 21 Midnight Madness (Annapolis) One of the highlights of the holiday season is Midnight Madness, giving bargain-hunters and last-minute shoppers an excuse to get out and shop well into the night. Stroll historic Annapolis and venture up Main Street to West Street, and over to Maryland Avenue. Stores pull out all the stops with holiday displays, treats, exclusive discounts, and sales for holiday shoppers. 4 p.m. - Midnight.

December 9 Eastport Yacht Club Lights Parade (Eastport) The magical Eastport Yacht Club Lights Parade takes place along the Annapolis Harbor and Spa Creek on the second Saturday in December every year. This annual tradition has been delighting holiday revelers for 40 years! View the parade aboard a tour boat to experience the holiday spectacle from the water. Or gather with friends and family along the neighborhoods of Eastport and Annapolis, where every street ending at the water offers a perfect view!

December 7-10 Annapolis Holiday Market (Annapolis) This season, stroll, shop, and be entertained along the Annapolis waterfront with an artisan market reminiscent of European holiday markets. The open air stalls line the city dock waterfront area of historic Annapolis, Maryland, and admission is free, so bring the whole family and peruse handcrafted goods, art, clothing, and more!

December 16 Santa Speedo Run (Annapolis) Don your best Speedo and festive Santa attire for a unique Annapolis tradition, The Santa Speedo Run! Money collected from registrations goes back to local charities like the Boys & Girls Club and the Anne Arundel County Food Bank. Racers and spectators are also invited to bring an unwrapped toy to the after-party to donate to Toys for Tots. Live music, drink specials, and festive conviviality conspire at O'Brien's Restaurant and Bar post-race.

December 27 Military Bowl Parade, Tailgating Festival, and Bowl Game (Navy-Marines Corp Memorial Stadium, Annapolis) The Military Bowl is back and better than ever! Join college football fans in Annapolis on December 27, 2023, for a parade down historic Main Street featuring the Budweiser Clydesdales, and an epic pregame to one of the most exciting bowl games in the Mid-Atlantic. The ACC vs. American conference matchup kicks off at 2:00 p.m. Stay in Anne Arundel County and enjoy all the Arundel Mills shopping and entertainment district has to offer. Or opt for historic charm and the walkable downtown district of Maryland's historic capital, Annapolis. TICKETS are now available!

December 31 New Year's Eve Celebrations (County-wide) Celebrate the start of a new year with fireworks and events throughout Anne Arundel County! Book a stay in the Arundel Mills region for gaming and live entertainment at Live! Casino & Hotel Maryland. The City of Annapolis also puts on an all-ages fireworks display along the shores of the Annapolis waterfront. Watch from the shore or book a memorable experience on a dinner cruise and view the fireworks display from the water! To explore accommodations in the region and learn more about dining, NYE specials, and other events, click HERE.

But wait, there's more!

For more holiday events and festivals throughout Annapolis & Anne Arundel County, from A Christmas Carol and the Nutcracker to Chef's Dinners and memorable tours and lights displays, check out our holiday events page and start planning your winter getaways today!

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