As the cold breeze grows stronger and cheeks grow redder, it is the perfect time to start planning winter activities with your friends and family. The holiday season is always filled with love, joy, and warmth, so family and friend outings should be as well. Whether you live in New England or are planning a trip here, the number of winter and holiday activities is overwhelming, so let me tell you some of my favorite places to be in the chilly weather!
- Boston’s Snowport
Not only does Snowport have free entry, but it’s also filled with a huge variety of markets, activities, and entertainment. In the heart of Boston, a town called Seaport is annually converted into a winter wonderland (see what I did there) from November 7 to December 28, 2025. Snowport is known for its large marketplace that includes shops where you can buy Christmas trees, holiday decorations, winter-themed treats, and so much more. On top of that, they have live music every Monday known as “Mohegan Music Mondays” where a band or singer will come in to play favorite holiday tunes live right in front of you. If this hasn’t enticed you enough, Snowport also has curling lessons and “Presents Place” where you can take the family Christmas card photo for the year.Â
- Boston Pops
If the outdoors aren’t really your thing and you’re looking for a warm winter wonderland, I’ve got you covered. By making your way down to Symphony Hall in Boston, you will find live music that will grace your ears and easily become your new favorite way to listen to all kinds of holiday music. The Boston Pops are a famous orchestra widely known for their firework spectacular on the Fourth of July on the Charles River. Although not as widely known, but still very popular, this orchestra performs a lovely mix of all kinds of holiday music for everyone. Between the incredible visuals and the visitation from Santa Claus, it is the perfect event for people of all ages.Â
- Walk Through & Drive Through Light Shows
Last on my list, but certainly not least, are the countless amounts of light shows that New England puts on. Whether you decide to visit one in western Massachusetts or one tucked away in the corner of Maine, these light shows are a cannot-miss event. Most shows have thousands, if not a million, of colored lights set up in creative ways to make the darkness of the cold winter nights a little more bright. You can stay warm by picking one that you can drive through and under, or you can pick one that reflects the variety of colors off your cold face. Either way, light shows are extremely popular here and I will always highly recommend going to one of them.Â
The winter season is one full of light and love, so by sharing this list with you, I hope I can make your winter this year a little more memorable and create memories that will last a lifetime. Have fun and stay warm!Â