Hiking Boston - Blue Hills Reservation Skyline Trail

Hiking the Blue Hills Reservation south of Boston is an experience no visitor or Beantown resident should miss. The Blue Hills, managed by the Massachusetts Department of Conservation and Recreation, encompass 7,000 acres of land with varied terrain and scenic views, making it a perfect destination for hiking. The crown jewel of the Blue Hills is the Skyline Trail - a 10-mile route that crosses over most of the park's most prominent summits.

At the Skyline Trail Head

The route I describe in this post starts on Willard Street in Quincy, travels nine miles of the Skyline Trail to the summit of Great Blue Hill, at 635 feet above sea level, then loops back around to the reservation headquarters. You will need either two cars or a friend to pick you up at the end of the trail, but this small inconvenience will make it possible for you to enjoy one of the Boston area's greatest outdoor adventures. For the two car option, leave one car at the park headquarters on Hillside Street and drive to the trailhead located at the Shea Rink parking lot on Willard Street in Quincy.

A vernal pool provides a great place to contemplate life on the Skyline Trail

The initial part of the walk is serene, with very little elevation gain. After about half a mile or less you will come to Wampatuck Road. Once you cross here you will be on a fire road, but you won't stay on it for long. Make sure you look out for the trail, which veers off to the left. From here you begin your steady ascent to the sweeping views of Boston and the greater Massachusetts Bay area that give the trail its name.

The morning sun pierces through a twisted tree on Rattlesnake Hill

The first hill you will come to is called Rattlesnake. The trail here winds up and around a placid vernal pool, its still waters perhaps belying a storied past as a romantic water hole dating back to the days when the native, pre-colonial Massachusett people would come at the end of summer to prepare for winters here. The rocky, precarious descent from Rattlesnake Hill and the subsequent climb and descent of Wampatuck Hill will give you just a taste of the scrambling you will have to do on a number of the more than 10 hills you will traverse on your journey.

The Skyline Trail hike is an up-and-down-and-up-and-down adventure!

Next you will cross Chickatawbut Road, then the trail steadily rises past the Blue Hills Reservoir and you are treated to some amazing changes in scenery. Climb steadily to a grove of young aspens before descending again to pass through some older growth oaks and maples, then up again to a grove of stumpy conifers, where you can find a nice flat rock to sit on to have a mid-morning snack.

Cut through this grove of young aspens en route to Nahanton Hill

The nourishment here is a good idea, as you will have three successive hills to climb – Nahanton, Kitchamakin, and Chickatawbut, which is topped by a fenced-in learning center with an inaccessible lookout tower, a solar panel array, and several bird houses. Once you pass this, you will make a steep descent to Randolph Road at the 3.6 mile point.

Looking northwest from the broad, clear summit of Buck Hill

Cross Randolph Road and you will began a rapid ascent of Buck Hill, which provides the broadest 360-degree views of the day, despite the fact that this is not the highest peak you will summit. Look to the northwest and on a clear day you can see all the way to Wachusett Mountain in Central Massachusetts and Mount Monadnock in Southern New Hampshire. The Boston skyline and harbor are visible to the north and east. And enjoy trying to pick out locations along the South Shore as you try to see all the way down to the Cape.

Moving on, you will descend Buck, which leads to another steep ascent. This is Tucker Hill. Once you summit Tucker, make your way down its western slope to arrive at Hillside Street, at just past 6.5 miles, where there is a picnic table situated under the shade of a large tree just in front of the ranger’s headquarters, perfect for a shaded lunch before pressing on to finish your hike.

At the ranger’s station you will find a bathroom and a source of water to refill. Make sure you drink plenty of water, because this last portion of the trail has some precarious ups and downs that will require you to have all your balance, which is aided with proper hydration.

From the headquarters take the northern branch of the trail across the scenic and quite challenging Hancock, Hemenway and Wolcott hills en route to Great Blue Hill. This is the nine-mile mark. Once here, climb the stone tower at Blue's summit and snap one last shot of Boston's skyline before continuing along the south branch trail some, which you will find some meters to the south of the tower.

View of Boston from Great Blue Hill

Before setting off on this final leg of your journey, you might want to text your pick up so he or she will be there waiting for you at the rendez-vous point on Hillside Street.

On this final spur, you climb one more major hill – Houghton. Before reaching Houghton's summit, though, you will have to climb two smaller hills, each increasing some in elevation before dropping back down into notches. Since only Houghton Hill is listed on the available maps for the Blue Hills, I personally refer to the hills leading up to and including Houghton as the Three Brothers. And Houghton is definitely the meanest of the three, with a final descent from his summit that's a steep and rocky pain!

As you are descending the east face of Houghton Hill, you will see Hillside Street below. This is where the footing gets tricky, so pay attention to the trail and don't rush things. You will be pretty tired by this point, and you don't want to make a silly mistake that will end in a twisted ankle or worse.

If you're doing this hike in the fall, winter or spring, you will be glad to know that just down the road you will find a hot cup of coffee waiting at the local Dunkin' Donuts. All said and done, you will have hiked 10-miles with an elevation gain of around 2,500 feet, and it will have taken you between five and seven hours.

Here are the quick stats for this hike:

Trailhead: At the Shea Rink parking lot on Willard Street in Quincy
Distance: 10 miles
Elevation Gain/Loss: 2,500/2,500 feet
Map: This entire area is well marked. A free PDF map is available from Blue Hills Reservation. You can also buy a hard copy of the map at the ranger's station for $2 - proceeds benefit the Trailside Museum. NOTE: There was a mistake in the most recent printing of the Blue Hills Reservation map and brochure which deletes the south branch of the Skyline Trail that returns to the ranger station via Houghton Hill. However, I have spoken with a park ranger who assures me that the full Skyline Trail is still open. Call the ranger station at 617-698-1802 if you have any questions.
Hiking Time: Depending on your pace and how many breaks you take, this hike can take from five to seven hours.
Best Times to Hike: This hike is great year-round, although take special care when hiking during rainy or snowy conditions as most of the hike involves hopping from rock to rock, and these rocks can get slippery when wet.
Difficulty: Moderate to Difficult. This hike requires a certain level of physical fitness and the ability to do some light scrambling.

Map showing the full north and south branches of the Skyline Trail

If you plan to try this trail, or have any questions, feel free to shoot me a comment below. And also, follow me on Twitter @MyFitLife2Day and check out my other blogs, MyFitLife2Day and Man of Merit. I'm also on HubPages at brianschwarz.hubpages.com.

Happy hiking!