Al N.
Yelp
As a parent of a four year old and a two year old, I find myself spending a lot of time at the Larz Anderson playground--one of the best in the Boston area. First of all, most of the playground is shaded. Second, there are many structures, all of which are kept in good shape and which the kids use and enjoy. There are bathrooms (kept reasonably clean, considering they're by a playground) and drink vending machines.
The park itself is immaculately kept. There's a pond with bridges, a gazebo, carp, ducks and the vermin called Canadian geese.
I don't skate, so I can't write about the skating rink. There's two baseball fields, a soccer field, and one huge hill that's great for kite-flying or rolling down.
The picnic areas (including the large closed-in one) have big tables and grills, but you have to reserve them and pay. It's cheaper for Brookline residents, which is kind of annoying because they have more money than the rest of us to begin with. If the money helps keep the park in the amazing shape it's in, it's worth paying for.
Parking lot can fill up fast, especially if there's a game. The street parking is a little scary when you're there with kids, but I've never not found a spot.