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.

This hike is challenging, with many hills to ascend on a rocky, sometimes narrow and steep trail. As the name implies, though, the Skyline Trail takes you along the many Reservation ridges, offering wonderfully scenic vistas and providing a great feeling of open space.

From the parking lot, take the small trail that heads north for a quarter of a mile until you reach an intersection with blue and orange marks. Blue marks are those of the Skyline Trail that you will take for most of the hike. Follow the marks left to start the hike.

After about 1.5 mile you will reach Hillside street, at which point you will have covered roughly one quarter of the hike. Cross the street carefully and head for the Reservation Headquarters on the right. You will be able to take a Reservation map there. Follow the blue marks behind the buildings to continue the hike on the Skyline Trail's northern branch. You will successively ascend Hancock Hill, Hemenway Hill and Wolcott Hill before you head for Great Blue Hill, at an altitude of 635 ft. You will first see Eliot Tower, an observation tower from which you will have a great view over the Boston skyline far away. You can continue on the Skyline Trail for less than a quarter mile to reach the observatory itself.

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 northeast 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 2070, 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.

Allow about 5-6 hours for the round-trip at a moderate pace.