Located in the heart of Maryland, Annapolis & Anne Arundel County is the ideal destination for celebrating winter adventures. Named a 2022 Best Christmas Town in the U.S.A. by Travel & Leisure, Annapolis is a magical place for creating holiday memories with family and friends.

To make it easy for visitors to craft unique holiday experiences, Visit Annapolis & Anne Arundel County (VAAAC) has compiled a handy list featuring activities from the shores of the Chesapeake Bay to the heart of the Arundel Mills gaming and entertainment district.


Arundel Mills - A Shopping Center
Arundel Mills Mall in Hanover is the largest discount retail shopping destination in the State!


November 25 Black Friday Shopping at Arundel Mills Mall (Hanover) Need the perfect gift at the ideal price? Consider a trip to Maryland's largest discount shopping center, Arundel Mills Mall. Saks OFF Fifth, Kate Spade, and Foot Locker are among the 200+ stores offering discounts of up to 70% off everyday prices. Dining and entertainment options abound, with activities for the entire family, along with Live! Casino & Hotel, the State's most significant gaming venue.


November 26 Small Business Saturday (Anne Arundel County) Shop locally this holiday season to experience the best that small business owners have to offer. Your friends and family will appreciate the unique gifts you're destined to find. Purchasing gift cards is another way to thank your favorite Annapolis & Anne Arundel County restaurants, shops, inns, B&Bs, cruise companies, performing arts venues, attractions, and service providers for enlivening the destination all year long.


November 27 Grand Illumination (Annapolis) Join the Downtown Annapolis Partnership and the Annapolis Jaycees as they ring in the holiday season at Market Space near Annapolis City Dock from 4:30 p.m. until 7:00 p.m. The annual Grand Illumination and tree-lighting festivities include dancing, caroling, and a special visit from Santa.


Christmas Tree Night Photo
The Grand Illumination of downtown Annapolis occurs Sunday, November 27, 2022.



December (weekends)  Jolly Express Cruise (Annapolis) Ho, Ho, Ho! Santa returns to the shores of Annapolis with his Jolly Express Cruise. Enjoy a 45-minute "sleigh ride" up Spa Creek aboard the Miss Anne that includes plenty of hot cocoa, holiday music, and good cheer. Bring your own blankets to stay cozy and warm. Cruises depart on the hour from 4:00 p.m. through 7:00 p.m. on select dates in December. $25/adult; $13/child (11 & under).


December 1, 8, and 15 Midnight Madness (Downtown Annapolis) Downtown Annapolis stores along Main and West Streets and Maryland Avenue stay open until midnight giving bargain-hunters and last-minute shoppers an incentive to get out and about and shop well into the night. Holiday displays, festive treats, and exclusive discounts make Midnight Madness Holiday Shopping one of the most anticipated holiday events of the year. 4:00 p.m. – midnight, December 1 and 8; 4:00 p.m. – 11:00 p.m., December 15.


December 1 – December 18 Horse and Carriage Rides (Parole) Annapolis Town Center offers horse and carriage rides on weekends throughout the holiday season. Book your ride on their website and enjoy hot chocolate or champagne as you experience a relaxing journey destined to get you into the holiday spirit. Carriage rides are limited to four guests each, with one ticket required per person.


Join Santa on the Jolly Express!



December 1 – 24  White Christmas (Annapolis) Classic Theatre of Maryland's White Christmas is based on the beloved 1954 film. The musical adaptation features the music of Irving Berlin and centers around a successful song-and-dance act and a duo of singing sisters. Performances of the heartwarming classic full of love and laughter take place Thursday-Sunday. Tickets: $55-$75


December 1 – December 30 North Pole Lights Walk (Severn) Take a self-guided walk to the North Pole. Let the North Pole Fairy get you started on your way through a garden of flowers and arctic animals to the North Pole Palace on select dates in December. Visit Santa in the Garden Cabin. $8/adult; $5/child 12 and under.


December 1- 31 Miracle at Live! Casino & Hotel (Hanover) Looking for a fun and festive way to celebrate the holidays this year? Look no further than Miracle. They are located in Club 21 on the 21st floor of Live! Hotel, the ultimate Christmas-themed pop-up cocktail bar, offers an immersive holiday experience with over-the-top traditional decorations and themed cocktails. Reservations are strongly recommended.


A light display with reindeer spelling out 'Lights on the Bay'
Lights on the Bay at Sandy Point State Park.



December 1 – January 1, 2023 Lights on the Bay (Sandy Point State Park) Enjoy more than 70 animated and stationary light displays depicting regional and holiday themes during a two-mile scenic drive along the shores of the Chesapeake Bay at Sandy Point State Park. Proceeds benefit the Anne Arundel County SPCA. Gates open at 5:00 p.m. daily through January 1, 2023. Tickets: $20 per car; $30 for large passenger vans, mini-buses, and trolleys; $50 for buses.


December 3 Colonial Yuletide Celebration (Annapolis) You are cordially invited to celebrate a colonial holiday with Historic Annapolis. Bring the entire family to welcome yuletide at the William Paca House and Hogshead. It's the year 1772, so you'll be experiencing holiday traditions, music, and stories of Christmases past from 2:00 p.m. until 6:00 p.m. Advance registration is strongly recommended. 


December 4 Annapolis Chocolate Binge Festival (Annapolis) Shop for sweet and delectable treats, savor hot cocoa and coffee specialties, and marvel at a collection of locally-made Gingerbread Houses on display at the 26 West Street Visitors Center through December 11th. Want to add to the Gingerbread House village? Click HERE for details. Be sure to catch the Grand Illumination at 5:00 p.m. on December 4. A flip of the switch on a canopy of lights will turn West Street from Church Circle to Madison Place into a winter wonderland. Learn more about the event and purchase tickets HERE


December 8-11 Annapolis Holiday Market (Annapolis) New this year, you and your family are invited to stroll, shop, and enjoy local entertainment at a City Dock holiday market reminiscent of European holiday markets. The free event will include handcrafted goods, artwork, clothing, and more.


A black family works on a Kwanzaa craft at a table
Celebrate Kwanzaa at the Banneker-Douglass Museum!



December 10 Annual Kwanzaa Celebration (Annapolis) Presented by the Banneker-Douglass Museum (BDM), this year's Kwanzaa celebration will focus on the creativity (Kuumba) of the people of the African Diaspora. Visitors can explore BDM's new exhibit, The Radical Voice of Blackness Speaks of Resistance and Joy while enjoying live performances, meeting with representatives of Black-owned businesses, and sampling delicious food from across Maryland. 


December 10 Eastport Yacht Club Lights Parade (Annapolis City Dock and Spa Creek) Magic will take place at the Annapolis Harbor from 6:00 p.m. to 8:00 p.m. as dozens of boats illuminated with thousands of colored lights and crewed by jolly revelers warm a chilly winter night. Families and friends will gather along the waterfront at their favorite viewing spots to watch the 40th Anniversary event nominated for Best Holiday Parade in USA Today's 10Best Readers' Choice contest. Individuals can vote daily through Monday, December 5.


December 18 Navy Men's Basketball vs. Washington College (Annapolis) Join the Navy Midshipmen as they take on Washington College at noon. Tickets: $10/adult; $5/youth.


EYC lights parade
Eastport Yacht Club Lights Parade.
Photo by Bob Peterson.


December 18 City of Annapolis Menorah Lighting (Annapolis) Gather at City Dock in Annapolis to celebrate Chanukah, the Jewish Festival of Lights. Hosted by Chabad of Anne Arundel County, the festival begins with a car parade from Forest Drive to Downtown Annapolis. Chanukah takes place December 18-26, 2022. 


December 28 Military Bowl Parade, Tailgating Festival, and Bowl Game (Navy-Marine Corps Memorial Stadium, Annapolis) The Military Bowl, presented by Peraton, benefitting the USO, will match a team from the Atlantic Coast Conference (ACC) against an opponent from the American Athletic Conference (AAC). Kickoff is at 2:00 pm. Morning festivities include a 10:00 am parade led by the famous Budweiser Clydesdales from City Dock to Navy-Marine Corps Memorial Stadium. A not-to-be-missed tailgating party gets underway at 10 am. Spend the night in Anne Arundel County and enjoy all the Arundel Mills shopping and entertainment district offers. Or opt for the historic charm of walkable Downtown Annapolis.   


December 31 New Year's Eve Celebrations (County-wide) Kick off 2023 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. Traditionally, the City of Annapolis puts on an all-ages fireworks display in the early evening, followed by midnight fireworks at City Dock. Visitors have watched from the shore or have booked a dinner cruise to welcome the New Year from the water. You can explore the region's accommodations and learn more about dining, New Year's Eve specials, and other activities HERE


Military Bowl at Navy Marine Corps Stadium
Military Bowl Parade and College Bowl Game.
But wait, that's not all!


For a complete list of 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 events page and start planning your winter getaways today!  

For holiday parking tips and information, please click HERE.

Please visit our media hub to download a curated album of photos for this release. 


Fireworks over the Annapolis harbor light up the night sky
Fireworks over the Annapolis Harbor during New Year's Eve.