This 1.6 mile loop hike at the Blue Hills Reservation in Milton, Massachusetts covers a small portion of the Skyline Trail (blue blazes), part of the Dark Hollow Trail (green blazes), and part of the Headquarters Path Trail.
From the main parking lot, across the street from the state police station, take the trailhead for the Skyline Trail and follow the blue blazes until you reach the top of Tucker Hill and see an intersection with green blazes. Follow the green blazes north, as this is the Dark Hollow Trail. The Dark Hollow Trail will lead you downhill from Tucker Hill toward Chickatawbut Road. Once you reach the part of the trail where Chickatawbut Road connects with Hillside Road, you'll hop directly onto the Headquarters Path Trail, which leads directly back to parking to complete the loop.
Views: There isn't much for views on Tucker Hill, but there's a small lookout-type area.
Explore our Appalachian Trail (AT) section hikes
Mt. Katahdin, MaineExplore our Pacific Crest Trail (PCT) section hikes
JMT/PCT Duck Pass Trailhead to Vermillion Valley, CaliforniaMyHikes is an independently-owned platform aimed to make exploring public trails easier for everyone. MyHikes has no investors, no shareholders, and no goal to profit - we share trail data for the fun of it and put a ton of time tracking, writing about, and publishing new trails each month.
But it takes money and a lot of time and effort (including espresso shots) to run the site. Our content is and always will be free to use, including interactive trail maps and elevation charts, pictures from the trail, and dope points-of-interest like vistas, overlooks, waterfalls, backcountry campsites, abandoned structures, and more...
So we simply ask that if you find our content helpful or useful when planning your outdoor excursions that you consider making a small donation to help keep our lights on.
You can become a Supporter* (*MyHikes account required) when donating to unlock perks. Or you can Donate without an account.
Either way, thanks for checking out MyHikes and have a great hike!
- Dave
Founder /
Admin