Homewood Suites by Hilton Boston/Canton, MA

This route makes a loop around the western side of Great Blue Hill. First, you will pass the bottom of Blue Hills Ski Area before heading up the Skyline Path. The top of the hill is home to several radio towers. Just past this is Eliot Tower. From here you can look out towards Boston. After enjoying the view, head back downhill.

The Skyline Trail can be accessed from Route 138, parking is across the street in a large lot. You will head up to the top of Great Blue Hill which has several radio towers on top and then continue over to Eliot Tower. Continue along the North Skyline Trail and South Skyline Trail making a small loop before heading back downhill.

A point-to-point hike across the Blue Hills, mostly following the Skyline trail. Easily done using public transport without the need to drive. Take a train to the 128 Route station and from there, follow the Blue Hill Drive until you reach a small, easy-to-miss path on the left-hand side of the road, heading downhill. Follow the path under the I-95 and head right, along the I-95 slipway, and toward Little Blue Hill. Beyond the Little Blue Hill, you need to cross a road and head up the Great...

Park in the ski area parking lot then head up the northern-most ski slope. Continue up to the summit of Eliot Hill then work your way around to Wolcott Hill, Hemenway Hill, Hancock Hill, then Houghton Hill before returning via the Accord Path Trail to the base of the ski area. There are plenty of good viewpoints along the way.

This route goes over several high points in the park including Great Blue, Wolcott, Hemenway, Hancock, Tucker, Buck, and Houghton Hill. There are plenty of awesome views of the surrounding area and the Boston skyline along the way. Sections of the trail are not well marked, so downloading the map ahead of time is recommended.