Milton/Quincy/Braintree/Canton/Randolph is home to this really big reservation called Blue Hills. I recently took the kids on a little hike there. There are a bunch of little hikes that the kids can do. Parking is free and the place is pretty huge so it can be sort of intimidating. Here are some quick hikes you can do if you need to get your kids out and about. These are taken from the brochure "Ranger Tom's Suggested Hikes" that can be found at the headquarters and trailside museum.
From the Reservation Headquarters (located down the road from Houghton's Pond - at 695 Hillside St. in Milton)
Skyline Loop - 3 miles. The entrance is right near the Reservation Headquarters. The signs should say "North Skyline Trail".
Hancock Hill - .5 mile. This is just a mini version of the Skyline Loop. Start at the same starting point and stop at the first hill and come back.
Wolcott & Border Path - 2.5 miles. Follow the Wolcott Path approx. 1/2 mile to the Five Corners intersection (five trails coverage). Upon reaching Border Path (intersection 1135), turn right and continue to intersection 1175. Turn right and follow the path past intersection 1178 and back to Wolcott Path.
From Houghton's Pond (pretty easy to find - it's on Hillside St.)
Houghton's Pond Loop - .75 miles. Just walk around the pond.
Dark Hollow Loop - 2 miles. Start at the little house there at Houghton's. Walk toward the bathhouse. Follow the green dots which begin past the bathhouse and loop around the base of Tucker Hill. Follow the green dots to the Skyline Trail (blazed in blue) and head uphill to the summit of Tucker Hill.
Buck Hill Loop - 3.5 miles. From the Houghton's Pond house/bulletin board, follow the red dots toward the beach and bathhouse. Follow the red dots over Breeze Hill to the intersection of the red dot and green dot trails. Here you have the option following the red dot loop either direction. Either direction will loop you back. This is a pretty challenging course.
From the Trailside Museum (located on 138 just by the Canton line).
Wolcott Path Loop - 2 miles. Starts just north of the museum. Follow the green dots starting at the bulletin board.
Great Blue Hill - 1 mile. Follow the red dots just north of the museum at the bulletin board.
For more detailed information about the Blue Hills and all that jazz, CLICK THIS LINK HERE TO GO TO THE DCR SITE.