Located in the heart of Maryland, Annapolis & Anne Arundel County is an ideal destination to welcome the fall and holiday season! You can access more than five hundred miles of shoreline, and craft a unique Chesapeake Bay adventure.
See magnificent holiday lights, cruise the water, run the Bay Bridge, and shop fantastic holiday deals. Fun holiday experiences are waiting for you, at the water’s edge!
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.
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.
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 18 – December 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.
November 20 – January 2, 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 be in retail heaven! Family dining and entertainment abound with activities for the whole family. 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.
November 25 Jolly Express Cruise (Annapolis) Ho, Ho, Ho! 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 and a jolly red nose 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 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 terrific 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.
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.
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