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About


Great Blue Hill
Milton, MA, Canton, MA, Quincy, MA

Trailheads, measurements, times, distances, and maps are all approximate and relative to the hike(s) as shown below.

Looking down the Big Blue ski trail on the way to Great Blue Hill

Route: Big Blue ski trail, (Great Blue Hill), bushwack, (Great Blue Hill lookout tower), Skyline Trail North, (Wolcott Hill), Skyline Trail North, unknown trail, (Hemenway Hill), Hemenway Hill Path, unknown trail, Skyline Trail North, (Hancock Hill), Skyline Trail North, Skyline Trail, (Tucker Hill), Skyline Trail, (Buck Hill), Skyline Trail, (Tucker Hill), Skyline Trail, Skyline Trail South, (Houghton Hill), Skyline Trail South, (Great Blue Hill), unknown trail, Big Blue ski trail

I needed to get away from the snow up in the mountains, so I decided to head south for a hike.

Since there seemed to be a lot of people on the foot trails, we decided to ascend directly up Great Blue Hill via the Big Blue ski trail, going by (gasp) two piles of snow on the way. The steep ascent was a great warm up.

After reaching the observatory, we followed an obscure trail as a shortcut to the lookout tower. The obscure trail became so obscure that it ended up being a bushwack. Nonetheless, we made it and were able to get nice views of the Boston sky line.

From there, we headed down the north branch of the Skyline Trail over to Wolcott Hill. Though brief and relatively tame, the trail did get steep in a few places. The views from Wolcott Hill were nothing special, though it was neat to look back at the structures on Great Blue Hill.

From there, we headed to Hemenway Hill. In going to the high point, I left the Skyline Trail and ended up in a maze of secondary trails. Realizing we were way off course when we reached one of the numbered intersections, we headed south toward Hancock Hill, rejoining the Skyline Trail after a few minutes, for the short and steep final approach to the summit.

The views from Hancock Hill were excellent, via multiple spur trails.

Our next stop was Tucker Hill. The descent down Hancock Hill was somewhat steep, before leveling out as the trail crossed the road.

There was a decent view point on the trail near the highpoint of Tucker Hill, followed by a steep descent into the col between it and Buck Hill.

Arriving at Buck Hill, we were greeted with, in my opinion, the best views of the day. The somewhat bald summit featured vistas in all directions, with a particularly nice view of Boston and the ocean. I couldn't help but laugh when I saw a large cairn located near the summit - a bit much for a 496 foot hill!

After having lunch at the summit of Buck Hill, we headed back over Tucker Hill, stopped at the vending machine near the road, then headed up the steep ascent to Houghton Hill.

Unfortunately, there were no decent views from the trail or highpoint of Houghton Hill.

From there, we headed up the somewhat steep back side of Great Blue Hill, stopping in the gift shop upon summitting. After that, we descended down the ski slopes and called it a day. Not a bad day of hiking, considering we were practically in the city!


Hike Ratings
Getting To Trailhead: Easy
Destination: Great Blue Hill
Length: Easy
Steepness: Difficult
Navigation: Easy
Views: Excellent
Crowds: Heavy
Destination: Wolcott Hill
Length: Moderate
Steepness: Difficult
Navigation: Easy
Views: Moderate
Crowds: Heavy
Destination: Hemenway Hill
Length: Moderate
Steepness: Difficult
Navigation: Moderate
Views: Excellent
Crowds: Heavy
Destination: Hancock Hill
Length: Moderate
Steepness: Difficult
Navigation: Easy
Views: Excellent
Crowds: Heavy
Destination: Tucker Hill
Length: Moderate
Steepness: Difficult
Navigation: Easy
Views: Excellent
Crowds: Heavy
Destination: Buck Hill
Length: Moderate
Steepness: Difficult
Navigation: Easy
Views: Excellent
Crowds: Heavy
Destination: Houghton Hill
Length: Moderate
Steepness: Difficult
Navigation: Easy
Views: Minimal
Crowds: Heavy


Hike Stats
Date Hiked: Saturday, April 19, 2008
Hike Commenced: 10:19 AM
Parking Elevation: 235'
Destination: Great Blue Hill
Ascent Commenced: 10:24 AM
Summit Reached: 10:34 AM
Time Elapsed: 00:10
Trailhead Elevation: 265'
Summit Elevation: 635'
Vertical Gain: 370'
Destination: Wolcott Hill
Ascent Commenced: 10:44 AM
Summit Reached: 10:54 AM
Time Elapsed: 00:10
Trailhead Elevation: 600'
Summit Elevation: 470'
Vertical Gain: 110'
Destination: Hemenway Hill
Ascent Commenced: 10:55 AM
Summit Reached: 11:09 AM
Time Elapsed: 00:14
Trailhead Elevation: 470'
Summit Elevation: 470'
Vertical Gain: 148'
Destination: Hancock Hill
Ascent Commenced: 11:09 AM
Summit Reached: 11:27 AM
Time Elapsed: 00:18
Trailhead Elevation: 300'
Summit Elevation: 510'
Vertical Gain: 163'
Destination: Tucker Hill
Ascent Commenced: 11:33 AM
Summit Reached: 12:00 PM
Time Elapsed: 00:27
Trailhead Elevation: 300'
Summit Elevation: 499'
Vertical Gain: 302'
Destination: Buck Hill
Ascent Commenced: 12:01 PM
Summit Reached: 12:27 PM
Time Elapsed: 00:26
Trailhead Elevation: 300'
Summit Elevation: 496'
Vertical Gain: 326'
Destination: Houghton Hill
Ascent Commenced: 1:02 PM
Summit Reached: 2:03 PM
Time Elapsed: 01:01
Trailhead Elevation: 300'
Summit Elevation: 420'
Vertical Gain: 559'
Hike Ended: 3:03 PM
Hike Time Elapsed: 04:44
Hike Vertical Gain: 2,458'



The bottom of the Big Blue ski trail


Looking at Boston from Great Blue Hill


Looking up the Skyline North Trail on the way to Wolcott Hill


Looking at Great Blue Hill from near the summit of Wolcott Hill


The Skyline North Trail on the way to Hemenway Hill


Looking at Great Blue Hill from near the summit of Hemenway Hill


Looking up the Skyline North Trail near the summit of Hancock Hill


Looking at Boston from Hancock Hill


The Skyline Trail to Tucker Hill


Looking at Great Blue Hill from Tucker Hill


Looking up the Skyline Trail near the summit of Buck Hill


Looking at Boston from the summit of Buck Hill


Looking up the Skyline South Trail on the way to Houghton Hill


The lack of a view as seen from the summit of Houghton Hill




Directions to trailhead: Take Exit 2B off I-93 onto 138 North. Shortly thereafter, the ski area and museum parking lots will be on the right side of the road.

Back to Great Blue Hill Profile
Back to Wolcott Hill Profile
Back to Hemenway Hill Profile
Back to Hancock Hill Profile
Back to Tucker Hill Profile
Back to Buck Hill Profile
Back to Houghton Hill Profile




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