MAINE TRAIL FINDER: "Pleasant Mountain is southern Maine’s tallest mountain at 2,006 feet. The nearly ten mile trail network offers a variety of moderately challenging day hikes. The summits provide commanding views of the White Mountains to the west and spectacular views to the east."
Alex McDaniel posted an initial route and FKT. He wrote:
The Blue Hills Skyline Trail is located in the Blue Hills Reservation, in Milton, MA, just minutes from downtown Boston. The Reservation covers 7,000 acres of rugged, forested landscape. There are an amazing 125 miles of trails in the Reservation. A 2-page brochure with trail map is here. The classic trail in the park is the 9-mile, blue blazed Skyline Trail.
ADMIN NOTE: This is a Premier Route - read the Guidelines. You must announce your attempt in advance, and track your attempt diligently; live-tracking is recommended for Premier Routes.
It has a solid history in the Fastest Known Time Of the Year Awards: