Chicktawbut Hill is the highest elevation on the Eastern side of the Blue Hills. The actual summit area is actually fenced on the north side and views are limited on the top. However there is a Lookout tower located on the north side of the hill with excellent views as well as on the western side of the hill there are great western views of Buck Hill and Great Blue Hill.
The Skyline Trail passes right by the summit of Chicktaawbut Hill in fact one of the more interesting sections of the trail passes right over the western side of the hill where the trail carefully traverses the side of a steep ledge which provides the good views of both Buck Hill and Great Blue Hill. Often this shot with the proper lighting can give one an impression of being out in the mountains and not being only a couple miles from downtown Boston.
The Hill itself is one of the more built up hills in the park and it even has an education center on the north side of the hill.
FROM THE CHICKATAWBUT OVERLOOK PARKING AREA: From I-93 get off on Exit 5 and head north on Route 28 toward Boston. Take it through the notch between Buck Hill and Chickatawbut Hill. Make a right on Chickatabut Hill Road and take it passed the Education Center Entrance. Parking will be located right by the overlook and there will be a trail heading south from there.
FROM THE BUCK HILL PARKING AREA: From I-93 get off on Exit 5 and head north on Route 28 toward Boston. The trailhead will be the third parking area on the left. It is located right in the Notch.
There are no fees at the park. However the park is only open sunrise to sundown.
Camping is prohibited in the Blue Hills Reservation.
Here are a number of different numbers for more information.
Blue Hills Reservation
Blue Hills Trailside Museum (617) 333-0690
Park Number 617-722-1188
Blue Hills TrailWatch (617) 698-1802.