Fall: Foliage and apple picking
Bostonians know you can get some beautiful views by driving out of the city for an hour or so. Foliage in the Boston area tends to peak around the middle of October, although it can vary depending on the amount of rain in the summer and the temperatures in early fall.
One excursion: Head west on Rte. 2, past Rte. 128/I-95. You'll immediately start seeing impressive foliage (look to your left at the reservoir just past 128). After a few miles, Rte. 2 takes a sharp left at a large intersection.
For Ye Olde New Englande Quainte, go straight; after a couple of miles of country roads, you'll come into downtown Concord, with lots of little shoppes (and within walking distance of historic Old North Bridge, site of one of the battles that launched the Revolution).
For more foliage and apples, though, follow Rte. 2 west. Stop at Arena Farms, on your right, for candied apples, fresh cider, pumpkins and flowers. You can't miss it - look for the giant mound of pumpkins.
A number of apple orchards are clustered around I-495, another eight or so miles past the turn. You buy a bag, then go out into the orchard and pick any of a variety of apples (some farms also have pears). There are few things cuter than little kids picking apples in an orchard. Map and listings.
On the way back, get onto 495 south for more foliage and the entrance to the Mass. Turnpike, which will get you back to Boston faster (and which has some pretty foliage as well).
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