Blue Hills has more than 125 miles of trails for all levels, in a setting that is surprisingly rugged and challenging. The Skyline Trail is originally a 9-mile long hike that crosses Blue Hills from east to west and requires two cars to ferry you from one end to the other. The hike we suggest here avoids this drawback and takes you for a loop on some of the most impressive sections of the Skyline Trail. In particular, you will climb Great Blue Hill, the highest point in the Reservation and the location of a weather observatory. Look at some of the records indicated on the monument facing the observatory entrance and you will be amazed at how bad the weather can be up there.

To come back, retrace your steps to find the southern branch of the Skyline Trail somewhere between the observatory and the Eliot Tower (stone with mark indications). Follow the marks until you reach again Hillside street south of the Reservation headquarters. Walk north along the road and cross it to take the Skyline Trail again on the other side. Instead of following the blue marks that quickly bear left and up Tucker Hill, however, continue straight on Bugbee Path. When you reach the intersection marked with number 2270, turn left to follow orange marks. You will follow them for more than a mile until you reach an intersection where orange and blue marks join. Follow these marks on the right and turn right at the next intersection. This is the trail that will take you back to the parking lot.