For some reason, my girls always called our favorite outdoor ice cream stand Dairy George (instead of Dairy Joy) and the nickname stuck in our family. In fact, the formal name of the stand is Cedar Hill Dairy Joy, but no matter how you say it, it makes for an excellent spring, summer, or autumn outing.
We discovered Dairy Joy when the girls were barely toddlers, and to this day they're still smitten with the clams, cones, burgers, and dogs. (If they could have their weddings there, I think they would.) Situated on the Weston/Lincoln line, the atmosphere is decidedly rural (you'll feel as if you traveled farther than your odometer might indicate) and picnic-y (there are fifteen or so picnic tables available).
Dairy Joy makes for a fantastic fair weather outing but it also works well in inclement weather. One rainy afternoon, my family of four enjoyed our lunch and then lingered under the overhang and played cards (we always carry a deck) happily for hours.
If you don't feel like heading to Weston just for a soft ice cream or soda, you'll find that there's plenty else to do in the area with or without children: for example, Drumlin Farm, the DeCordova Sculpture Park, and Pierce Park, which has no playground equipment but is a huge green space in which to run and play and offers lovely, well marked trails in the woods.
My husband and I think the lobster rolls are the best in Maine and Massachusetts where we've sampled quite a few. Also take note: Dairy Joy does not take credit cards and is not for the faint of wallet: the lobster rolls cost $20. Still, on a warm summer day, even though you might wait in a long line for your savory or sweet treat, I think you'll find a happy family atmosphere that makes it worth the wait.
Cedar Hill Dairy Joy, 331 North Avenue, Weston; 781-894-7144