GO Get Fit #1: Great Blue Hill via Skyline Trail
Bluebird day at the Blue Hills
The trip report
Written by Carl · last updated by Conrad the DJ on Mar 23, 2025
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About this event
Join us for a hike in the Blue Hills Reservation in Canton, MA. (Karen Read talk is encouraged. :))
This is the #1 ranked hike in Massachusetts according to AllTrails and a great way to start the GayOutdoors 2025 Get Fit series. This is a 3-mile hike with 813’ of elevation gain and is considered easy to moderate. Be prepared for muddy conditions. Some may find trekking poles helpful. This path goes to the Eliot Observation Tower, which, if open, offers spectacular views of the Greater Boston area. There is a multi-year project to restore the tower and pavilion area, so this visit it may not be open.
The parking lot is located across the street from the MA State Police’s H7 office, which is located at 685 Hillside St, Milton, MA 02186. After, we can grab a bite at South Shore Plaza, which is about 10 minutes away. This trail should take us a little over an hour to complete. I hope you can join us!
AllTrails map: https://www.alltrails.com/trail/us/massachusetts/great-blue-hill-via-skyline-trail
GayOutdoors’ 2025 Get Fit Series
- Saturday, March 22nd – Blue Hills Reservation in Canton, MA: 3 miles & 813’ elevation gain
- Saturday, April 5th - Middlesex Fells Reservation in Medford, MA: 4.2 miles & 524’ elevation gain
- Saturday, April 12th - Wachusett Mountain in Princeton, MA: 4.8 miles & 1,154’ elevation gain
- Saturday, April 19th - Breakheart Reservation in Saugus, MA: 5.3 miles & 590’ elevation gain
- Saturday, May 3rd - Boston Harbor Walk in South Boston, MA: 6.75 miles & no elevation gain
- Saturday, May 10th - Leominster State Forest in Leominster, MA: 7.4 miles & 685’ elevation gain
- Saturday, May 24th - Mount Monadnock via White Dot Trail in Jaffrey, NH: 3.4 miles & 1,745’ elevation gain













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