Unwrap the Magic: Annapolis' Must-See Holiday Events of 2023
December in Annapolis is a whirlwind of festive cheer and exciting events, making it a perfect time for residents and visitors alike to experience the holiday magic in this charming city. Here’s a roundup of must-attend events, complete with dates and where to find more details:
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Midnight Madness: A unique shopping experience awaits you at the Midnight Madness event, happening on December 7th, 14th, and 21st. Stores in downtown Annapolis along Main Street, Maryland Avenue, and West Street will stay open until midnight (or 11:00 pm on the 21st). It’s a fantastic opportunity for bargain hunters and last-minute shoppers to find great deals in a festive atmosphere. click here for more info.
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The Annapolis Holiday Market: From December 7th to 10th, the Annapolis Holiday Market offers a delightful shopping experience. Open from 7 pm to 10 pm on Thursday, 11 am to 9 pm on Friday and Saturday, and 11 am to 5 pm on Sunday, this market is a great place to find unique gifts and enjoy the holiday spirit. click here for more info.
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Annapolis Town Center Menorah Lighting: Celebrate the start of Hanukkah on December 7th at the Annapolis Town Center. Join the community at 5 pm to light the first candle on the Menorah, a symbol of light and hope. This event is located across from J. Alexander’s Restaurant. click here for more info.
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Eastport Yacht Club Lights Parade: On December 9th, from 6 to 8 pm, witness the spectacular Eastport Yacht Club Lights Parade. This event is a visual treat, with boats adorned in festive lights creating a dazzling display on the water. click here to learn more
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Holiday Performance at St. Anne’s Church: For those who love music and performance, December 15th, 16th, and 17th are dates to mark on your calendar. St. Anne’s Church will host a breathtaking performance featuring a world-class soloist, the Chamber Orchestra, and the Annapolis Chorale. Check out liveartsmd.org for ticket information. click here to learn more.
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Christmas at the Westfield Annapolis Mall - Santapolis: A Magical Holiday Experience: For a memorable Santa experience, visit the Westfield Annapolis Mall. Santapolis offers a magical setting with twinkling lights and festive décor. Santa’s elves will guide you through this enchanting world. Available through December 24th, this is the perfect opportunity to capture holiday photos with Santa. Additionally, on December 4th and 11th, pets can join in for a photo with Santa, too! While there, don’t miss the Salvation Army’s Angel Trees in the CPK Court and the food court. Pick an angel, shop for their gift, and deliver the unwrapped present to the Salvation Army on Hilltop Lane by December 11th. for more details, click here.
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Lights on the Bay: Running from November 19th, 2023, through January 1st, 2024, the Lights on the Bay event is a spectacular display of holiday lights along the Chesapeake Bay. Open Monday through Thursday from 6–10 pm and Friday through Sunday from 5–10 pm, it’s a delightful experience for all ages. The light show is even open on holidays, offering a fantastic opportunity to enjoy the festive lights with family and friends. click here for more info
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Homestead for the Holidays at Homestead Gardens: This event transforms Homestead Gardens into a winter wonderland, complete with 23 uniquely themed trees and a range of delightful events. The atmosphere is filled with the refreshing scent of fresh greens, and visitors can enjoy the warmth of the festive spirit. A highlight of the event is the appearance of Santa Claus, providing an unforgettable experience for the whole family. Be sure to also check out their Preview Party and Grand Illumination for a mesmerizing display of lights and holiday magic. click here for more info.
These events are not only a celebration of the holiday season but also a reflection of the vibrant community spirit in Annapolis. Whether you’re shopping at the Midnight Madness event, enjoying the lights displays, or participating in the various festive activities, Annapolis offers a little something for everyone during the holiday season. Remember to check the respective websites for more details and any updates on these events.
Jen Holden, Realtor® | Principal
The Jen Holden Group of Compass
📱 443.803.7620 (m) | 📞 410.429.7425 (o)
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