Experience the quirky and prideful Eastport vs. Annapolis Tug of War, shop at the largest discount shopping destination in the state of Maryland at Arundel Mills, run the Chesapeake Bay Bridge in our county's Bay Bride Run, or plan a weekend in Annapolis for the Veteran's Day Classic Basketball Tournament at the United States Naval Academy


Music, sports, shopping, and entertainment are waiting for you, at the water's edge, along the shores of the Chesapeake Bay this November in Annapolis & Anne Arundel County. 


Michael Joseph Harris plays a guitar on stage (man in a black and white photo with a beard and wearing a hat)
Michael Joseph Harris of Hot Club Baltimore will play at this year's Annapolis Jazz & Roots Festival.
 Image courtesy of Annapolis Jazz & Roots Festival.


November 1 An Unveiling of the Annapolis Port Marker (Annapolis) On Tuesday, November 1, 2022, County Executive Steuart Pittman, Mayor Gavin Buckley, and the Annapolis Port Marker Committee will unveil the Annapolis Port Marker naming Annapolis, Maryland, as a "Site of Memory" in coordination with United Nations Educational, Scientific and Cultural Organization (UNESCO) Slave Route Project. Join community leaders and attendees at Asbury United Methodist Church for the commemoration with a dedication ceremony immediately following at Susan B. Campbell Park in downtown Annapolis. 11:00 am – 1:00 pm. 


November 4-6 & November 11-13 Annapolis Jazz & Roots Festival (Eastport) Celebrate the Sounds of New Orleans with GEORJAZZ; experience the best of Flamenco Jazz, Pop & Rock with the Juanito Pascqual Trio; sing along to Chesapeake Bay Songs & Sea Chanteys, and so much more! Stay in historic downtown Annapolis or book a local short-term rental for two weekends of culture, history, and, best of all - jazz and live music! 


November 5 Fall Foliage Bay Lighthouse Cruise (Annapolis) This beautiful cruise includes three Chesapeake Bay lighthouses and a spectacular view of the lovely fall foliage along the Annapolis waterfront. A historically attired lighthouse keeper provides live interpretation for a thoroughly enjoyable cruise. Saturday, November 5th - 10:30 am - 1:30 pm. 


watermark journeys
Cruise the bay for a Fall Foliage Tour or visit Santa's Jolly Express!
 Image courtesy of Watermark.


November 5 Tug of War, Slaughter Across the Water (Eastport vs. Annapolis) The Tug of War, a celebration of the geographical and, some would argue, philosophical differences between Eastport and Annapolis, is a not-to-be-missed maritime event unlike any other. The Tug begins at noon! Gather at 2nd Street in Eastport or Susan Campbell Park on the Annapolis side for a bit of rebel-rousing, drinks, food vendors, and an all-around good time. 


November 10 Radical Voice of Blackness Speaks of Resistance and Joy (Annapolis) Guest curated by Myrtis Bedolla of Galerie Myrtis, this art exhibition by fifteen Black Maryland-based artists, as well as works from the Banneker-Douglass Museum's Fine Art Collection implores the viewer to examine historical and contemporary themes of Black joy and healing created in opposition to and despite oppression. The exhibit's opening reception is on November 10th, 6:00 – 9:00 pm. This ongoing exhibition will run daily through September 30, 2023. 


November 11 Veteran's Classic, Basketball at the United States Naval Academy (Annapolis) Head to the USNA for the 9th Annual Veterans Classic. This men's basketball event honors veterans of all service branches. At 6 pm, St. Joseph's will take on the University of Houston. At 8:30 pm, Midshipmen will face the Princeton Tigers. Reserved Tickets: $40, General Admission Tickets: $25, tickets are good for both games! 6:00 pm – 11 pm. 


Fredrick Banneker Bicentennial Celebration
Experience the latest exhibit at the Banneker Douglass Museum.


November 12 Navy vs. Notre Dame NCAA Football (Baltimore) A college football game so big they had to move it to M&T Bank Stadium! The game kick-off is at noon. Book your stay in the BWI Hotel Region and enjoy all of the region's amenities, including public transit, for ease in and out of Baltimore. Play in Arundel Mills and enjoy shopping at Arundel Mills Mall, gaming, and entertainment at Live! Casino, Maryland, and so much more! Click HERE for a list of BWI area hotels. 


November 13 The Bay Bridge Run (Annapolis-Stevensville) This EPIC 10K race traverses the eastbound span of the Bay Bridge from Anne Arundel County to Kent Island in Queen Anne's County and finishes with a huge post-race party! The views and photo ops abound, and this race is bringing in running enthusiasts from across the country, so act fast to secure your spot. Click HERE for registration. 


November 13 Sweet Potato Fest (Lothian) A new fall tradition, the fest will feature live music, creative kids' activities, sweet potato digging, face painting, a bounce house, corn pools, and a special farmers market with vendors selling different sweet potato varieties and sweet potato treats! The farmer's market is ONLY for those who have bought tickets to the Sweet Potato Fest. KIDS 3 & Under FREE, KIDS 4-12 yrs. $10/each, ADULTS 13 & UP $25/each. The festival will run for one day only, 11:00 am – 3 pm. 


Bay Bridge Run celebration village at the end of the finish line.
The Celebration Village at the Bay Bridge Run.
Image courtesy of the Bay Bridge Run.


November 13 Rams Head Presents Lindsey Buckingham (Annapolis) Buckingham is one of his generation's most inventive and electrifying musicians. Under Buckingham's direction, Fleetwood Mac became one of the best-selling and most beloved rock groups of all time. Hear this unprecedented artist at Maryland Hall for the Creative Arts in an intimate setting. Tickets, $75.00 - $224.00 - accessible seating available. The show begins at 7:30 pm. 


November 18 Annapolis Town Center Christmas Tree Lighting (Parole) In one of the best holiday towns in the country, we kick off the season as soon as possible! Come to Annapolis Town Center for caroling, hot chocolate in the Paseo, performances from the Maryland Performing Arts Center, and the big guy himself, Santa! 6:00 pm – 8:00 pm, Tree Lighting at 6:15 pm. 


November 18December 18 Horse and Carriage Rides (Parole) Annapolis Town Center brings the holiday magic with 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 the holiday magic of the season. Carriage rides are limited to 4 guests, with one ticket required per person. Tickets are $60 each. 


A lit holiday sign at night
Lights on the Bay at Sandy Pont State Park benefits the AASPCA.
Image courtesy of Visit Annapolis & Anne Arundel County.


November 20 – January 1, 2023 Lights on the Bay (Sandy Point State Park) Lights on the Bay is an annual holiday light show featuring a two-mile scenic drive along the shores of the Chesapeake Bay through Sandy Point State Park, with more than 70 animated and stationary displays depicting regional and holiday themes. All proceeds benefit the Anne Arundel County SPCA! Tickets: $20.00 - PER CAR | $5.00 - 3D Glasses | $30.00 - LARGE PASSENGER VANS, MINI-BUSES AND TROLLEYS | $50.00 BUSES. Gates open at 5:00 pm, recurring daily through January 2, 2023. 


November 25 Black Friday Shopping at Arundel Mills Mall (Hanover) Need the perfect gift at the ideal price? Consider a shopping trip to Maryland's largest discount shopping center, Arundel Mills Mall! With Saks OFF Fifth, Kate Spade, Foot Locker, and 200+ stores offering discounts of up to 70% off everyday prices, you may just be in retail heaven! Family dining and entertainment abound with activities for the whole family, along with Live! Casino & Hotel, the state's largest gaming venue. Please see the mall website for holiday hours of operation. 


November 25 2022 Jug Bay Post Turkey 5K Trail Run (Lothian) Work off all that turkey with this scenic 5K in South County. All proceeds will go to the Friends of Jug Bay to fund the purchase of kayaks, which will support their outdoor education programs along the Patuxent River. Cost: $15 per person, ages 12 and older. 


Arundel Mills - A Shopping Center
Black Friday shopping at Arundel Mills.
 Image courtesy of Arundel Mills.


November 25 Jolly Express Cruise (Annapolis) Ho, Ho, Ho, and a Bottle of Rum! Well, maybe not the rum, but Santa returns to the shores of Annapolis with his Jolly Express Cruise! 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 own blankets to stay cozy and warm. Cruises are available on select dates throughout November and December. Cost: $25/Adult $13/Child (11 & Under) Cruises depart at 4:00 PM, 5:00 PM, 6:00 PM, 7:00 PM. Visit the Watermark website to book your adventure! 


November 25 White Christmas (Annapolis) Classic Theatre of Maryland presents White Christmas November 25 - December 24, 2022. Based on the beloved 1954 film, this musical adaptation features the music of Irving Berlin and centers around a successful song-and-dance act and a duo of singing sisters. A perfect start to the holiday season, book tickets for a heartwarming classic full of love and laughter. Cost: $55- $75, recurring weekly on Thursday, Friday, Saturday, and Sunday. 


November 26 Small Business Saturday (Anne Arundel County) Experience the best small business owners have to offer and pledge to shop locally this holiday season. When you shop locally, your friends will appreciate something unique and special. Gift cards are also a great way to gift to your favorite downtown Annapolis & Anne Arundel County restaurant, shop, inn or B&B, sailing cruise, performing arts venue, or other county attraction. 


Christmas Tree Night Photo
The Grand Illumination of the Annapolis Chrismas Tree will take place at Market Space on November 27th.
Image courtesy of Bob Peterson.


November 27 Grand Illumination (Annapolis) The Downtown Annapolis Partnership joins the Annapolis Jaycees as they ring in the holiday season in downtown 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 pm with dancing, carols by local school groups, and a special visit from Santa! Make this Annapolis Holiday event a part of your family's traditions! 4:30 pm – 7:00 pm. 


But wait, there's more! 

For more November events and festivals throughout Annapolis & Anne Arundel County, check out Visit Annapolis & Anne Arundel County's events page and start planning your fall and winter getaways today! 


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