Ahh, Christmas time, the most wonderful time of the year. And while Annapolis, MD is always an adorable coastal town, it is especially charming at Christmas time. The cobble stone streets are lined with garland wrapped lamp posts, while lights twinkle, couples and families walk around with merriment and cheer. Sailboats in Ego Alley are even decorated for the holidays! Christmas in Annapolis is truly a special time, so I’ve rounded up some of the best Christmas things to do in Annapolis, MD!
(Last updated on November 5, 2022)
Snowflake Alley
Snowflake Alley is hands down my favorite thing to see in Annapolis during the holidays! It gets very crowded on weekend nights, so I always try to go during the week if I can to snap some pictures. One year, there was an elderly man who gave me and my friend light up necklaces just to spread Christmas cheer–I just about cried and I still have the necklace! I used to pretend that this was the setting of me meeting my Hallmark-esque Christmas tree farmer love of my life! You can find Snowflake Alley on Main Street in Cabbage Alley, which is near State Circle and Maryland Avenue!
Midnight Madness
Midnight Madness is “a Historic Downtown Annapolis holiday tradition that encompasses the charm and character of our most beloved memories of Norman Rockwell and Charles Dickens. We will adorn the streets and participating storefronts with holiday decorations, trees, garland, snowflakes, bows, and lights to create a Downtown Winter Wonderland.”
Midnight Madness is a great opportunity to see Snowflake Alley, but it will be busy. From 4 pm until midnight, walk through historic downtown and enjoy stores that stay open late, live music, hot chocolate, and overall merriment.
This year, in 2022, Midnight Madness will be happening on December 1, 8, and 15th (note that it ends at 11 pm on the 15th). It’s a great way to support local businesses, especially this year, and it’s a family friendly event!
For more information on parking, please check here.
Homestead Gardens
Okay, so Homestead Gardens isn’t technically in Annapolis, but it’s only a stone’s throw away in Davidsonville! Homestead Gardens is one of my favorite places for any season, but it’s especially mesmerizing at Christmas time. There’s a very large model train display that is fun for all ages, that is guarded by lifesize nutcrackers. There’s also an elf village and small (stuffed) reindeer stable. Of course, there’s plenty of Christmas things to purchase, as well, including fresh trees, outdoor decorations, state-of-the-art faux trees, and more. It’s truly a fun Christmas thing to do in Annapolis, MD!
The Homestead Grand Illumination is on November 19th and the event runs from 5 pm until 8 pm. Enjoy 25% off lighting + candles, live holiday performances, seasonal tastings, and more. Plus, a special appearance by Santa Claus.
You can also meet Santa and the reindeer every weekend beginning November 26th until December 18th. Reservations are required and they will not accept walk-ins, so book here now to meet the jolly man! December 2nd will be a special event with Santa, specially for the furry children with paws. This is a first come, first served event; find more information here.
Annapolis Town Center
Annapolis Town Center is usually one of my favorite spots, but that’s because it’s home to Target. The 2022 Christmas Tree Lighting Ceremony is on November 18th this year. The event is from 6-8pm and you can learn more about the event here.
If November is a little bit too early for Christmas celebrations for you, you can wait until December 10th for the Holiday Stroll. You’ll enjoy free hot chocolate, roaming carolers, sales at various retailers, and beautiful decorations.
You can also enjoy a Horse and Carriage ride every weekend from November 18th through December 18th., sipping on champagne or hot apple cider as you make your way through Town Center. Click here to make your reservation.
Town Center is also home to Santa’s Cottage! Here you can meet Santa and take home a family photo with him! This special guest arrives on November 21st, and Mrs. Claus will be visiting on December 14th. Check the calendar for the full list of times and special events with Santa!
If one visit with Santa isn’t enough, you can join him for breakfast at Tuscan Prime on December 11th. Reservations are required, so book here soon.
In addition to seeing Santa, Town Center is a great place to do some holiday shopping. In addition to the permanent stores like Anthropologie, Talbots, and Gallerie Z, Town Center is home to pop-ups so keep an eye out for some of those!
(Special note: If you also celebrate Hanukkah or know someone who does, there is a Menorah lighting in Town Center on December 18th).
Ego Alley–Decorated Boats
At Ego Alley, you’ll find a plethora of boats, many of which will be decorated for the holidays. Strolling around Ego Alley admiring the creative light displays is one of the most unique things to Annapolis and makes for very special memories. I love how the boaters get into the holiday spirit!
Are you planning a trip to Annapolis and need a place to stay? Check out this roundup of the best AirBnBs in Annapolis by the Naptown Scoop! Some of them are even boats–how neat would that be?
There you have it–some of the best Christmas things to do in Annapolis! I hope you’re able to check some of these off your Christmas bucketlist and enjoy our quaint, coastal town. And while you’re at it, call Hallmark and tell them to set a movie here next Christmas!
