If you like the cozy indoor life, get to your local library, volunteer, get to know the librarians. They know who likes to stay in to read, and might even know who might be single. And even if they don't, libraries are excellent places to be, and many could use a helping hand. Maybe start a book club or movie night for mud season, when even the most avid hikers tend to take a break.

I would think a good real estate buyer’s agent would be helpful here, in looking for towns that would allow this, and then looking for land in those places. Also, as others have mentioned, some of what you can do cam be done with a land trust.

I don’t know, but I’d expect significant speed restrictions on all the roller coasters…

In Allston, it's usually faster to get downtown to take a bus to the red line than to walk to the green line.

My understanding is the opposite, that they don’t pay their fines, and the city has given up on going after them.

The Brattle is running a Marx Brothers movie fest on 1/1, and their popcorn is good.

The Brattle and the Coolidge Corner Movie house have interesting offerings throughout the year. If you like movies, it worth keeping an eye on the schedules. Both have food options in a range of price points nearby. (also Harvard Film archive is worth considering)
https://brattlefilm.org/
https://coolidge.org/

https://harvardfilmarchive.org/

You may want to check out which T tracking apps are reliable, because I suspect you may want to use the 86 bus as well as the green line, but life in Brighton without a car is feasible, especially if you are looking at meeting people in Cambridge or the Back Bay. Parking can be challenging in Brighton, its so much worse in those other locations.

Yep, at 3-4 inches my mom would let me go ice skating on the marsh near the house, but ice on the lakes/ponds had to be a lot thicker before she'd let me go skating with friends.

When I was a kid (1970s80s) we used kerosene lanterns for light during outages, we even had a ships lantern, that we could hang to make sure we had light in the evenings. You cant read by one of those, but you can make dinner and play board games. (we already had a wood stove and a hand pump so lights were the biggest change).

A lot depends on where you need to go. It's relatively easy to get to downtown from most places, but it can take an absurd amount of time to get say, from some parts of the North Shore to Cambridge, because you have to go in through the city center and back "out" again, there are few direct routes unless you drive, and taking multiple buses is not just slow, but playing with fate.

You may find this helpful, to see where the service gaps are. Many of the areas that are only served by buses are underserved.

https://www.mbta.com/maps

Ice Auger, if he doesn't have one.
Good snacks.
Airtight plastic bins for keeping critters out of the snacks.
Rechargable solar lamps (more for the summertime)

Those freestanding hammock frames are pretty great, not everyone has trees at just the right distance to tie up to.

Wait until they find out that when its really cold, Maine strippers only bare themselves down to their long underwear.

Not anymore. I think there are one or two specialty silk import places handing on, but that's it.

Wow. Thank you for posting. That is quite something. Makes me wish I had the money to settle into the Victorian Spa for a long weekend...

COM doesn’t bring in DOD money.

Also, all that cold and ice means you have great reasons to duck into a bar for a warming snack, or a drink.. or two.