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 20 wonderful ways to celebrate winter & 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!

A star ★ denotes my personal recommendations.

Annapolis Area Winter & Holiday Festivities

Photo by Visit Annapolis

Grand Illumination – November 27 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.

Polar Bear Plunge – February 4 in Annapolis

One of Maryland’s most popular winter traditions is the Polar Bear Plunge. Jump into the cold waters of the Chesapeake Bay to raise money for Special Olympics.

Baltimore Area Winter & Holiday Festivities

Festival of Trees – November 25-27 in Timonium

Come see a beautiful selection of decorated Christmas trees, gingerbread houses and more at the Festival of Trees.

★ 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. If you’re visiting Baltimore during the holiday season then this is the event I recommend the most.

Krampuslauf – December 3 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.
(I love how the website has notes everywhere that you should NOT give money to the poor people asking for money. What a great sentiment of the Christmas spirit.)

Monument Lighting – December 1 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.

Parade of Lighted Boats – December 3 in Baltimore

See boats on the inner harbor decorated and lit up for the holidays. In my opinion there’s nothing prettier than lights on the water.

Station North Holiday Market – December 10 in Baltimore

Baltimore hosts a lot of holiday markets and the Station North Holiday Market is one. Get local food and gifts in one of the city’s trendiest areas this December.

Zoo Lights – All season long in Baltimore

See Baltimore’s zoo dressed up in Christmas lights. It makes for a great family outing and also a romantic date night.
If the Baltimore zoo is too expensive, you can consider going to DC. Their Zoo Lights event is free and also spectacular.

DC Area Winter & Festivities

Gingerbread Contest & Show – Select dates in Upper Marlboro

I. love. gingerbread. And even though this gingerbread contest is held in a small rural museum, the submissions they get are actually really creative and well done. Admission is inexpensive so if you live in the area, it’s something worth seeing.

Holiday in the Park – Select dates in Bowie

Six Flags is Maryland’s most fun amusement park, and for the season they decorate for the holidays. Have a fun day at the park in winter with Holiday in the Park.

★ ICE! – Select dates in Fort Washington

ICE! is finally back after a few years’ hiatus. Put on a warm jacket and stroll through amazing ice sculptures at DC’s National Harbor.

★ Winter’s Eve – December 3 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:

• Christmas at Mount Vernon
• Old Town Alexandria

Eastern Maryland Winter & Holiday Festivities

Photo by Visit St Michaels

Christmas in St. Michael’s – December 9-11 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 3 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 2-3 in Chestertown

The Dickens festival is a small gathering of artists and others selling their crafts in the beautiful town of Chestertown. There are also day-specific events so check the calendar to see if anything in particular is of interest to you.

Southern Maryland Winter & Holiday Festivities

★ 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.)

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! ★

Related posts:

Things to Do & See in Annapolis, MD: a Local’s Travel Guide 38 Fun Things to Do in Baltimore A Local’s Travel Guide to Baltimore, MD (Things to Do & More) 29 Fun Things to Do in Maryland This Fall (2023) 7 Charming Towns on Maryland’s Eastern Shore 14 Easy Day Trips from Washington, DC (Updated 2023)

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