So I love visiting Boston, but haven't ever been in the winter. I love to be outdoors and downtown is great for that in the warmer weather, I've even found a few fun parks outside of the city that is good while visiting the suburbs. Curious what you gentlemen and ladies reccomend for during this time of the year that won't have me outside freezing and will keep me intrigued. I know museums are pretty great for this season but looking for some off the beaten path activities! Also any great holiday villages/Light displays/Christmas type of things to visit?

You can rent skates and skate the rink at strawberry banke (portsmouth)...and let me know if you do and want to meet up.

The ballet is a classic Boston event.  
I can go a lot of places with the title but I'm still digesting turkey and not thinking straight

I heard it is very funny and sexy

You can rent skates at Boston Common and skate at the frog pond.  People watching at Faneuil Hall during the holidays  is always interesting ( if not too cold)

Otherwise the place gets commandeered by the college kids and it turns into a real pain in the ass for anybody else who wants to skate. Avoid the ice bar at fanuel Hall. It is nothing at all like the one in Canada or Sweden. It is truly lame and not worth the money. If you go to boston.com you can find all sorts of things to do while you're here. There's lots to do even just outside the city which is a simple T ride away. Of course don't forget to dress warm because Boston in the winter time is frigid. Have fun and stay safe xo

I'm going to incorporate this into a dinner & dessert date for sure. Omg

If you don't mind a bit of a drive for something different I might suggest Tower Hill Botanical Garden located in Boylston Ma. Indoor garden, decorated and lit up nicely for the holidays.

Omg, I couldn't agree with you more!  A few years ago I went to the Ice Bar with friends.  Very big disappointment and highly over-priced....for everything!

I took my son and a couple of his friends there when they were on leave (army) I was totally embarrassed

The SOWA Vintage Market, near the South End is fun and indoors, year round on Sundays. There are some galleries in the area as well. There's also a Holiday Market in South Boston on December 3rd & 4th. The art schools - Mass College of Art and School of the Museum of Fine Arts have holiday sales of student work. It's good stuff. They're both near the Museum of Fine Arts.
I always like the Isabella Stewart Gardner Museum on a nasty winter day - the 4 story courtyard is a giant Italianate greenhouse.

For indoor fun...the New Eataly in the Prudential Center. New outdoor venue is Boston Winter Wonderland on City Hall Plaza. Skating, holiday shopping from local vendors and wine and beer.

Boston Museum of Science - whether you are a geek or not, this is a fun, interesting, never the same place twicekind of excursion. They also have an Omni theater that is OUT OF THIS WORLD. And simulation rides.