Located in the heart of Maryland, Annapolis & Anne Arundel County is a charming destination for celebrating winter adventures. Consistently ranked as a top-Christmas town year over year, Annapolis is a magical place for creating holiday memories with family and friends.
Visit Annapolis & Anne Arundel County has the scoop on unique holiday experiences and festive activities from the shores of the Chesapeake Bay to the heart of Arundel Mills gaming and entertainment district. Plan your winter on the Chesapeake getaway today!
Events
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Lights on the Bay 2023, Image courtesy of Jarvin Hernandez.
November 23 – January 1, 2025: Lights on the Bay
Enjoy a stunning two-mile drive featuring over 70 animated light displays at Sandy Point State Park. 🌌 Proceeds benefit the Anne Arundel County SPCA, so you can enjoy the lights while giving back!
November 29 - December 29: North Pole Lights Walk
Embark on a self-guided walk to the North Pole! 🌲 Follow the North Pole Fairy through a magical garden to the North Pole Palace. Don’t miss visiting Santa in the Garden Cabin. Tickets are super affordable!
December (weekends): Jolly Express Cruise
Ho, Ho, Ho! 🎅 Santa's back with his Jolly Express Cruise! Enjoy a cozy 45-minute “sleigh ride” on the Miss Anne, complete with hot cocoa and holiday tunes. Don’t forget to bring your blankets for extra coziness!
December 1: Grand Illumination
Kick off the holiday season with the Grand Illumination at Market Space near Annapolis City Dock! 🎄 From 3:00 p.m. to 5:30 p.m., enjoy dancing, caroling, and a special visit from Santa himself. Get ready to feel the festive vibes!
December 1: Annapolis Chocolate Binge Festival
Sweet tooth alert! 🍫 Indulge in delicious treats and warm beverages while admiring a fantastic Gingerbread House display at the 26 West Street Visitors Center. Don’t forget to check out the Grand Illumination on December 4!
December 7: Colonial Yuletide Celebration
Travel back to 1772 with Historic Annapolis at the Colonial Yuletide Celebration. 🌟 Bring the fam to the William Paca House for music, traditions, and stories of old-time holiday cheer. Advance registration is highly recommended!
December 10: City of Annapolis Menorah Lighting
Celebrate Chanukah with a festive menorah lighting at City Dock! 🕊️ Hosted by Chabad of Anne Arundel County, the festival kicks off with a car parade, bringing joy to all who attend.
December 14: Eastport Yacht Club Lights Parade
Experience the magic of the Eastport Yacht Club Lights Parade at Annapolis Harbor! 🎉 From 6:00 p.m. to 8:00 p.m., watch as dozens of boats adorned with colorful lights cruise through the waters. Gather with friends and family for the ultimate viewing experience!
December 31: New Year’s Eve Celebrations
Ring in the New Year with style! 🎊 Enjoy fireworks and events throughout Anne Arundel County. Book a stay in the Arundel Mills area for gaming and live entertainment or watch the fireworks at City Dock. It’s the perfect way to welcome 2024!
Arts & Entertainment
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Select Dates November-December: White Christmas
Catch the Classic Theatre of Maryland’s adaptation of White Christmas, based on the beloved 1954 film. 🎶 This musical features the enchanting music of Irving Berlin and runs Thursday through Sunday. Get your tickets now!
December 14, 15, 21, 22: Ballet Theatre of Maryland presents "The Nutcracker"
Discover the wonder of this timeless holiday tradition and allow yourself to be magically swept away by the tale of the young heroine Clara and her adventures to rescue her beloved Nutcracker from the Rat Queen’s evil spell.
Shopping
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November 29: Black Friday Shopping at Arundel Mills Mall
Who doesn’t love scoring a good deal? 🛒 Head to Maryland’s largest discount shopping center, Arundel Mills Mall, where over 200 stores are offering discounts of up to 70% off! Dining and entertainment options abound—perfect for a family day out! 🎁
November 30: Small Business Saturday
Support local this holiday season! 🎉 Shop at small businesses in Anne Arundel County to discover unique gifts that your friends and family will love. Don’t forget to grab some gift cards for your favorite local spots!
December 5, 12, and 19: Midnight Madness
Shop 'til you drop during Midnight Madness! 🕛 Downtown Annapolis stores will be open until midnight, offering exclusive discounts, festive treats, and a chance to soak in all the holiday displays. It's one of the most anticipated events of the year!
December 12-15: Annapolis Holiday Market
New this year, stroll through the City Dock holiday market for a taste of European charm! 🥨 Enjoy handcrafted goods, local entertainment, and more at this festive free event.
Sports
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November 10: Bay Bridge Run
Join the thrill of the Bay Bridge Run, a 10K race across the stunning Bay Bridge! 🌉 With breathtaking views and a vibrant post-race celebration, this event is perfect for runners and photographers alike. Plus, it’s a rare chance to run on a closed bridge!
November 16: U.S. Naval Academy Football vs Tulane University
Cheer on the Naval Academy football team vs Tulane at the Navy-Marine Corps Memorial Stadium! Tickets are on sale now online at Navy Events | U.S. Naval Academy (evenue.net)
December 28: Military Bowl Parade, Tailgating Festival, and Bowl Game
Don’t miss the Military Bowl! 🎉 Enjoy a lively parade featuring the famous Budweiser Clydesdales, followed by a tailgating party and the big game at Navy-Marine Corps Memorial Stadium.
But wait, there’s more! For a complete list of holiday events, from classic performances to chef dinners and light displays, check out our events page and start planning your winter getaway today!
And don’t forget about parking tips! 🚗 The City of Annapolis is bringing back free holiday parking from Thanksgiving to New Year’s.
So grab your crew and get ready for a holiday season to remember! 🥳
View the link for more events and to plan your stay today!
