The Holiday Season is probably my favourite of all, and I love to spend Christmas in Maryland. 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 25 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, that my readers may like.

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.

This page has been updated for the 2024 Christmas season. More events may be added as I discovery them.

Annapolis Area Winter & Holiday Festivities

Photo by Visit Annapolis

• Grand Illumination – December 1 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 recreational parks in the area.
• Lights on the Bay – All Christmas 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.
• Lights Parade – December 14 in Annapolis
  Not to be confused with the above, the Lights Parade is a one-day event where boats “parade” down the water, decked in beautiful Christmas lights.
• Military Bowl Parade – December 28 in Annapolis
  The Naval Academy has a large local following. The Military Bowl celebrates that, and the traditional parade to kick off the event is headed by Clydesdales, which may be my favorite part.
• Polar Bear Plunge – February 1 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 29-December 1 in Timonium
  Come see a beautiful selection of decorated Christmas trees, gingerbread houses and more at the Festival of Trees.
• Monument Lighting – December 5 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.
• Midnight Madness – December 6 in Ellicott City
  “Midnight Madness”es are becoming more popular in the area. Ellicott City is a super cute town with a lot of nice local businesses to support for the holiday season.
• Krampuslauf – December 7 in Baltimore
  Krampuslauf is an offbeat, alternative event that happens every year in the alternative city of Baltimore. Interested? Come join in!
• Parade of Lighted Boats – December 7 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 14 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.
• ★ German Christmas Village – All Christmas 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.
• ★ 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.
• Holly Days – All Christmas season in Baltimore
  This year, Baltimore Zoo is doing a variety of events geared toward children that includes crafts, Santa, and more.
  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

• ★ Winter’s Eve – December 7 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.
• 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.

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 (it’s completely lit up and decorated for Christmas)

Eastern Maryland Winter & Holiday Festivities

Photo by Visit St Michaels

• Crab Basket Christmas Tree Lighting – December 7 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 7th, crab baskets may be due beforehand.
• ★ Dickens of a Christmas – December 6-7 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.
• Yuletide Festival – December 7-8 in Earlesville
  For my history lovers: travel back to the colonial era with this Yuletide festival and holiday market.
• Christmas in St. Michael’s – December 13-15 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.

Southern Maryland Winter & Holiday Festivities

• A Magical Christmas Parade – December 7 in Solomons
  There are lots of parades for the Christmas season, but I chose to feature this one in Solomons because this cute bayside town always looks so lovely in its Christmas lights each year.
• ★ Garden in Lights – All Christmas 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 at Flat Iron Farm – Date TBD in Great Mills
  After a HIATUS, I’m glad Flat Iron Farm is back with its fun Christmas event! The date this year is TBD and it will be held in Bubby’s memory.

Though there are countless things to do in Maryland during the holidays, 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! ★

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