Buck Hill via Skyline
Those folks looking for a short family hike that is kid friendly, from preschoolers to seniors, would love this hour adventure. You can stretch it out if you pack a lunch to enjoy at the top of the hill as you take in the majestic views from Boston harbor, Dorchester Bay, Quincy Bay to Mt. Monadnock in NH.
Park on Route 28 in Milton on the west or northwest side of the road between Chickatawbut Rd and Rte 128. Follow the Blue Skyline Trail straight up the steps to the top of Buck Hill. The flat top is grassy with large boulders to sit on. There are many wild blueberries to pick in August, just remember to pick the ones with the crown on top.
You can elongate this hike by continuing down the other side and halfway up the next hill where we look for elephant rock, you will know it when you see it. Rest and come back if you are with little ones. If you go over that second hill, you will come to the Houghtons Pond area. Stash a car or get picked up, or turn around and go back if you have a couple hours.
Park on Route 28 in Milton on the west or northwest side of the road between Chickatawbut Rd and Route 93.