Our neighbors (the same ones who kindly share their bike trailer for grocery shopping, and who are serious about their family biking...their 4 year old is pretty solid on a 2-wheeler which I find rather impressive) were slightly horrified that we had never gone biking on the Minuteman Bikeway, which they insist is one of the best features of our neighborhood. It got to the point where Angela feared they might disown us if we didn't actually get out on this path, so on Labor day, at the last minute, we decided to try an actual recreational bike ride. We tend to see our bikes as utilitarian, and almost never go on recreational bike rides, so this was a big step!
We didn't go too far, just a quick couple miles to Spy Pond in Arlington. Unfortunately the playground was closed due to a sand wasp infestation, but we got a lot of mileage out of counting geese, ducks and swans, and running on the lawn. H was plenty happy riding along, and probably could have gone much farther once we got going. It was nice to feel like we got "out of the city" in just a few miles. For other folks who might like to try a ride on the Minuteman, it starts by Alewife station on the Red Line, and bikes are permitted on the red-line during non-rush hour on weekdays and all day on weekends. We'd love to hear about other car-free recreation options in the area, either by rail or bike or both, if anyone has some to suggest.