Fun Ways to Celebrate the Holiday Season in Maryland (2021)

The Holiday Season is probably my favourite of all. Though a lot of fun is had at home making cookies and watching wholesome movies, there’s a lot to do and much to see. Here, I’ve compiled a list of 15 wonderful ways to celebrate the holiday season here in Maryland. This is by no means a comprehensive list but rather events that I have been to or heard of myself.

Please note that I’ve put dates down for your convenience but you should always double check with the event website!

Annapolis Area Holiday Festivities

Christmas in Annapolis, Holiday Season in Maryland
Photo by Visit Annapolis

Grand Illumination – November 28 in Annapolis

See the lighting of the Christmas tree in beautiful downtown Annapolis. There will also be other holiday festivities such as ornament decorating and caroling.

Ice Skating at Quiet Waters – All season in Annapolis

Baltimore sets up an ice skating rink each year, but did you know Annapolis has one too? Enjoy the rink at Quiet Waters Park, one of the best rec parks in the area.

Lights on the Bay – All season in Annapolis

Visit a drive-through show of Christmas lights, Lights on the Bay. I personally like the drive-through because I get to stay in the comfort of my car.

Bonus: The Polar Bear Plunge isn’t a holiday-themed event but it’s still one of Maryland’s most popular winter traditions. Jump into the cold waters of the Chesapeake Bay to raise money for Special Olympics.

Baltimore Area Holiday Festivities

Miracle on 34th St, Holiday Season in Maryland

Cross St Market – Select dates in Baltimore

Do what Baltimore does best and support local business with Cross St Market’s annual Holiday Market. It’s a great opportunity to find a local gift for your family and friends!

German Christmas Village – All season in Baltimore

The Inner Harbor’s so beautiful at Christmas and the German Christmas Village is an absolutely amazing way to spend a night (or a few nights) during the holiday season.

Krampuslauf – December 4 in Baltimore

Krampuslauf is an offbeat, alternative event that happens every year in the alternative city of Baltimore. Interested? Come join in!

Miracle on 34th St – All season in Baltimore

Put on “world’s best” lists, the Miracle on 34th St show is a block of homes decorated extravagantly with holiday lights. I must say that it’s not something worth driving long and far to see, but if you’re in the area and have time, definitely pop over to 34th st.

Monument Lighting – December 2 in Baltimore

A lot of cities have a lighting of Christmas trees but Baltimore prides itself on its annual Monument Lighting. Come join the city in marking the start of the holiday season in the beautiful area of Mount Vernon.

DC Area Holiday Festivities

Winter’s Eve – December 4 in Accokeek

I’ve gone here since I was a small child, so I’m a bit bias, but Winter’s Eve is a fun night out. There are lots of crafts suitable for adults, some food and drink, roasted chestnuts, and a bonfire with caroling. The money goes to the host Accokeek Foundation, which teaches visitors about local history and sustainability.

Bonus: I love going to these northern Virginia events and places, so since they’re close by, here’s a list:

Eastern Maryland Holiday Festivities

Christmas in St Michaels, Holiday Season in Maryland
Photo by Visit St Michaels

Christmas in St. Michael’s – December 10-12 in St. Michael’s

St. Michael’s is locally known for going all out during the holiday season. See this charming town decked out for Christmas and attend a Lights on the Bay parade.

Crab Basket Christmas Tree Lighting – December 4 in Rock Hall

This event is different and a good tribute to Maryland’s unofficial mascot, the crab. In Rock Hall, people decorate crab baskets and use them to make a tree or two. While this event is on December 4th, crab baskets may be due beforehand.

Dickens of a Christmas – December 3-5 in Chestertown

I’ve never been but this 19th-century Christmas extravaganza looks fantastic! Chestertown is also a well-preserved and super charming colonial city.

Yuletide Festival – December 4-5 in Earleville

I’ve never been to this festival but colonial-era Christmas fests are the best. This one has a market, cooking demonstrations, and self-guided tours of the grounds.

Southern Maryland Holiday Festivities

Annmarie Gardens, Holiday Season in Maryland

Flat Iron Farm – All season in Great Mills

I went several years ago and absolutely loved it! The farm transforms into a Christmas town with shops, pony rides, a petting zoo, and more. Make sure you account for traffic because this event is very popular.

Garden in Lights – All season in Solomons

It’s a long drive for many but everyone enjoys going to Annmarie “Garden in Lights.” I have to say that I’m not a light show person but I actually love going here every year since they do such a great job. (Lights are not exclusively holiday themed.)

Christmas Corgi

Though there are countless things to do in Maryland during the holidays, and many events have been cancelled this year due to COVID, these are the ones I personally recommend or think look the most interesting. I hope to grow this list each year as I and my friends discover more and more to see.

★ I wish everyone a wonderful holiday season! ★

Posted on Wednesday, November 10, 2021 in Destinations
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