Heading down a steep decline on the way up the Skyline Trail.
Here on the South Shore, we have plenty of walking places – the beaches, the woods, numerous trails around ponds and through meadows. But what we lack is places to hike. Living at sea level, there just isn’t much for those of us who wish to go vertical.
Well, . . . except for the Blue Hills! It’s so easy to forget that over 7,000 acres of open space lie just to the north of us. The Blue Hills Reservation, based in Milton, is home to 125 miles of walking and hiking trails. Many of them pass through forests and around ponds, but quite a few also lead up and down steep, rocky hills. The views from the top are spectacular.
Managed by the state’s Department of Conservation and Recreation (DCR), the Blue Hills Reservation is open to the public every day from dawn to dusk. In season, it offers camping, fishing, skiing (cross country and downhill), swimming, non-motorized boating, and even golf. There are trails for mountain bikers and horseback riders, spots for picnicking and rock climbing, and an annual controlled and permitted deer hunt. Great Blue, the tallest of the 22 hills in the area, extends to an elevation of 635 feet.
The reservation extends from Milton and Quincy to Randolph and Dedham. The park itself has been open to the public since 1893, but long before that, the lands were home to the Massachusett, a Native tribe who referred to themselves as “people of the great hills.” When Europeans began arriving on our shores, they observed the hills from a distance and named them for their bluish color. You can view archaeological evidence of both Native and Colonial settlements within the reservation, and also visit the Blue Hills Weather Observatory, a National Historic Landmark.
People tell me all the time that the Blue Hills is on their list of Places To Visit . . . but they never seem to make it there. Perhaps it has something to do with proximity: it’s almost too close to plan a day trip around it, but too far away to stop by on a lark. Plus, there are so many trails to consider – where would you start? However I think that once you’ve been there, and you see how accessible the place actually is, those barriers aren’t so daunting.
I’d actually been hiking in the Blue Hills a few times before – maybe three times over the course of 25 years — but I still felt like I had a mental block against it. So I decided to plan a group outing there. With friends invited along, there would be no backing out because it suddenly became inconvenient to drive up to Milton on a Saturday afternoon.
We began our hike at 1pm. It was mid-November, and even though the trail guide indicated that it should take us about 2 hours to complete the course, we had lots of little legs with us (7 children ages 5 to 9, plus one yellow lab) and were concerned about getting back before the 4:30 sunset.
Departing from the Houghton’s Pond parking area, we followed a footpath along the side of Hillside Street to the Reservation Headquarters. We found a trailhead just behind the headquarters building, and following the directions I obtained from the excellent Friends of Blue Hills website, within a minute we made a right turn onto the Skyline Trail.
Our plan was to follow the Skyline Trail up to Eliot Tower and then down again. I find, when hiking with children, it’s helpful to have “something” to see at the top. Following the blue blazes, we immediately began to climb uphill, over rocks and through some steep passages. Before long, we were at the crest of Hancock Hill, enjoying the first of many great views of the Greater Boston area.
The Skyline Trail led us up and down wooded hills, over terrain that was more rugged than what you’d typically find on the South Shore, but not especially difficult. Because of the fallen leaves on the trail, there were a few times when I opted to scoot down steep declines on my behind, rather than risk slipping on the smooth rock surfaces. The boys and girls in our group seemed energized by the challenges of scrambling up and over each obstacle we encountered. Every so often, we’d crest a hill and find another, different view of the city. Eventually we reached the turn-off for Eliot Tower.
Most of the trails in the Blue Hills Reservation are clearly marked, not only with blazes of various colors, but also with wooden signs, the names clearly spelled out. You can download a map via the DCR website, or purchase one at the headquarters or at the Blue Hills Trailside Museum. I downloaded a PDF of the map, but finding the print to be small, I brought the file to a local copy shop and had it enlarged and printed in color. Another option is to download the (free) 16-page color “Discover the Blue Hills” booklet from the Friends of the Blue Hills.

Eliot Tower was constructed in the 1940s by the Civilian Conservation Corps. Originally envisioned as a rest area of sorts for hikers, the rough stone tower and its adjoining shelter once featured a large stone fireplace, terraces with inviting views, picnic tables and benches, and restrooms. Much of this still remains, but only in a generally “rustic” sense. The restrooms are boarded up, and the doors have been removed from the shelter, so the wind blows through. However the views – especially from the top of the tower – are inspiring, and the tables and benches offer a welcome place to sit and rest.

The author an her son on the Skyline Trail.
After pausing for a snack at one of the picnic tables, our group began its descent. Again, using the directions from Friends of the Blue Hills, we turned at Marker 1066 and followed the blue blazes all the way back down to Hillside Street. It was a different trail going downhill, with plenty more rocks to scramble over. We were back to our cars by 3:30pm. Overall, it was a very pleasant way to spend an autumn afternoon. We will definitely be going back.
For general info about the Blue Hills Reservation,, including driving directions, visit the DCR’s page on Blue Hills:
For more detailed trail and event info, visit Friends of the Blue Hills:
by Kezia Bacon
November 2015
Kezia Bacon’s articles appear courtesy of the North and South Rivers Watershed Association, a local non-profit organization devoted to the preservation, restoration, maintenance and conservation of the North and South Rivers and their watershed. For membership information and a copy of their latest newsletter, contact NSRWA at (781) 659-8168 or visit To browse 19 years of Nature (Human and Otherwise) columns, visit