As usual, I have been planning some bummels & jaunts for the winter. And even more usual, I probably won't be able to do half of them.
Here are a handful of ski trips that I'm considering, most of them are T accessible. So, if you have an opportunity to try one out let me know, I'd like to hear your report.
Town of Lincoln
The Lincoln Land Conservation Trust has protected over 1000 acres in Lincoln and has over 50 miles of trails. Most of the trails are perfect for xc skiing. In fact there are more winter trails than summer trails, since wetland areas are frozen and passable with skis. And getting there is easy, take the Fitchburg commuter rail from North Station or Porter Sq Station to the Lincoln Station, train schedule. Trail maps are also available at Lincoln Town Offices; I bought mine at the Town Library.
Our favorite urban bicycle trail is a great place to xc ski in the winter. A couple years ago I skied from Davis Sq to Arlington Center right after a storm. The Cambridge portion was already plowed, but the Somerville and Arlington section was great. Year round cycling has become more common and Arlington and Somerville plow their sections more frequently, so getting out soon after a storm is more important. I don't know whether Lexington and Bedford plow their sections, so you could take the 77 bus to Arlington Heights and ski into Lexington. The 76 and 62 busses will take you right into Lexington Center.
Or you can ski along city streets immediately after a storm. Saturday night storms are particularly good, since cities don't plow as regularly on Sundays.
The Middlesex Fells is a good option after a storm, though walkers pack the trails fairly quickly. The fire roads are nice and wide. They do tend to be stoney, so you need 6-12" of snow, and still you might want to take a pair of rock skis. The Friends of the Fells provide a very good map of the Fells. The following bus routes get you into the Fells, 99 from Malden, and the 132 from Malden, another option is to take the commuter rail to Winchester and walk the half mile to the Fells.
The Blue Hills
The Blue Hills provide great terrain and is easily accessible from the city. Most of the wide trails on their map are good ski trails. The rangers have even developed a Ski Routes pamphlet. As for access, it seems that bus route 240 from the Ashmont station provides access right to the heart of the the Blue Hills.
Now I understand that setting your own tracks isn't everyone's cup of tea, so here are a few more options.
Weston Ski Track
The Weston Ski Track is the closest cross country ski center. They groom, set tracks and even blow snow. It is near the 128 & MassPike interchange in, of course, Weston. But what's better, it is near two rail stations. Riverside, the end of the D line, and Wellesley Farms, on the Framingham/Worcester line. Both stations are about a mile away, though the ski trails are a little closer to Riverside.
Great Brook Farm
I will also share my favorite local cross country ski center, even though it is not transit accessible. That is Great Brook. It is an old farm in DCR land in Carlisle, which I think is better than the Weston golf course. They have ski rentals, and a wide variety of trails; some of the hills are a bit of a challenge. They even have a night skiing loop lit with kerosene lamps!
If you read this far, you should probably learn that I'm not only a fan of cross country skiing, but I do enjoy downhill too. Here are a couple downhill alternatives.
The Blue Hills, same ones mentioned above, also have a downhill ski area. It isn't really transit accessible, but it is close, especially if you live on the south side of the city. It might also be fun to take light backcountry skis, take the bus to the Blue Hills, and ski across the reservation to the downhill area.
This is another nearby DCR reservation. The roads in the reservation and to the top of the mountain are closed in the winter, which affords good cross country skiing. There is also a downhill ski area on the north side of the mountain. And of course, my favorite, they have a ski train!
I hope this whets your appetite for skiing this winter. If you make any of these jaunts, please let me know. I'm sure to share my own this winter.