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Ski
Hiking Trail Conditions Report
Peaks
Peaks Pine Hill, Wenepoykin Hill, Silver Mine Hill, Gerry Hill, Winthrop Hill, Money Hill, Nanepashemet Hill, MA
Trails
Trails: Quarry Road, Skyline Trail
Date of Hike
Date of Hike: Wednesday, May 21, 2025
Parking/Access Road Notes
Parking/Access Road Notes: I parked in what's basically a large paved pulloff with room for many cars to parallel park off of South Border Rd. Maybe between a half dozen to a dozen there around 4:15 and 7:30pm with room for several more. Note that the traffic backed up headed to the traffic circle just to the east was CRAZY at 4pm. I wasreally glad I was going the other way.  
Surface Conditions
Surface Conditions: Dry Trail, Wet Trail, Mud - Minor/Avoidable 
Recommended Equipment
Recommended Equipment:  
Water Crossing Notes
Water Crossing Notes: Trivial  
Trail Maintenance Notes
Trail Maintenance Notes: Old, large stepover about 15min north of Pine Hill, mid-sized, delimbed stepover about 15min after that, a couple of leaners/widowmakers above the trail just north of Sheepfold, large straddler about 15min north of Winthrop Hill, an absolutely MASSIVE pine tree came down somewhere in the very general vicinity of North Reservoir Dam I believe that's been partially delimbed. It was honestly so huge and covered such a wide swath of forest that there was a path around and I don't *think* it was the original trail but not sure. A small stepover just before this too. Mid-sized stepover still partially in the trail abut 30min before I ended, and a mid-large sized duck under about 20min before I ended. Skyline Trail is marked with white triangles and usually pretty frequently so.  
Dog-Related Notes
Dog-Related Notes: Dogs are allowed on-leash. Good trails for dogs.  
Bugs
Bugs: I think they were out but not awful as I was moving quickly.  
Lost and Found
Lost and Found: None 
 
Comments
Comments: A nice evening hike to finish my redlining of the Middlesex Fells area. This hike and my first in the reservation, Rock Circuit Trail, are both the most rugged, and most enjoyable in my opinion, going over some ledge (though this less so than Rock Circuit Trail) and more varied terrain. Note that you need to hike Quarry Rd to access the trail. No spurs technically needed on this one but the guidebook also mentions you can start at Sheepfold for a slightly shorter hike (unless you're redlining because you'd need the OAB on Quarry Rd still). Let me know if a track would be helpful. No parking/hiking after dark. I don't recall ground conditions too well but I don't think there was much mud and either way, trails were mostly dry. Cool to intersect with so many of the other trails I've hiked over the past couple of months and remember certain spots I'd been before. Gaia had me at 8.2mi, 850ft of gain, 3hr5min.  
Name
Name: Liam Cooney 
E-Mail
E-Mail: liamcooney96@gmail.com 
Date Submitted
Date Submitted: 2025-05-24 
Link
Link: https:// 
Disclaimer: Reports are not verified - conditions may vary. Use at own risk. Always be prepared when hiking. Observe all signs. Trail conditions reports are not substitutes for weather reports or common sense.

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