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        Bear Hill is a decently sized network with a variety of trail difficulties. The majority of the trails are intermediate technical singletrack or wider doubletrack/carriage roads, with a few higher difficulty trails as well. The region encompasses two main hills, Bear Hill and Millstone Hill, one of which is home to the MIT Haystack Observatory. On the far side of the observatory is the trail Hell's Gate, one of the most difficult trails in the local area.
        There are many entrances to the trail network, but only some have areas to park. The primary entrance is at the end of Cow Pond Brook Rd (Near the soccer fields).
        Primary Trail Type: Cross-Country
        Bridge Street Parking Area google parking directions
        Access Info:
        Parking and entrances at the end of Wilson Way, Cow Pond Brook Road, and Bridge Street.
        Activities Click to view
        Region Details
        • 3
        • 10
        • 21
        • 2

        Region Status
        Open as of May 11, 2026
        Local Trail Association

        Stats

        Avg Trail Rating
        Global Ranking
        #8,505
        State Ranking
        #3,320
        Trails (view details)
        36
        Trails Mountain Bike
        40
        Trails E-Bike
        1
        Trails Hike
        36
        Trails Trail Running
        36
        Trails Snowshoe
        8
        Trails Nordic Ski
        8
        Total Distance
        13 miles
        Total Descent Distance
        6 miles
        Total Descent
        1,275 ft
        Total Vertical
        223 ft
        Highest Trailhead
        410 ft
        Reports
        81
        Photos
        7
        Ridden Counter
        1,949

        Popular Bear Hill Mountain Biking Trails

        80 2.5 2,323 ft 22 ft 215
        Popular green difficulty singletrack. This multi-use trail can be used both directions and has a easy overall physical rating with a 22 ft green climb. Trail visibility is always easy to follow. On average it takes 2 minutes to complete this trail.
        75 0.0 3,320 ft 53 ft 120
        Popular green difficulty singletrack. This multi-use trail can be used both directions and has a easy overall physical rating with a 53 ft green climb. Trail visibility is always easy to follow. On average it takes 6 minutes to complete this trail.
        95 4.0 2,500 ft 53 ft 108
        Popular blue difficulty singletrack. This mountain bike primary trail can be used both directions. On average it takes 5 minutes to complete this trail.
        100 5.0 427 ft 0 ft 85
        A couple of nice rock rolls
        90 5.0 2,690 ft 8 ft 83
        Technical singletrack with a descent down .
        100 0.0 2,595 ft 5 ft 82
        Popular blue difficulty singletrack. This multi-use trail can be used both directions and has a moderate overall physical rating with a 5 ft blue climb. Trail visibility is always easy to follow.
        95 0.0 1,503 ft 20 ft 78
        Popular blue difficulty singletrack. This multi-use trail can be used both directions and has a moderate overall physical rating with a 20 ft blue climb. Trail visibility is always easy to follow.
        85 0.0 922 ft 0 ft 76
        Trail on top of the old berms that were made as part of the quarry.

        Recent Ride Log Activity in Region

        Today
        • 0 rides
        Yesterday
        • 1 rides
        Past Week
        • 4 rides

        Bear Hill Mountain Bike Routes

        23 miles 1,787 ft 27
        Loop that connects MIT and point beyond.

        Photos of Bear Hill Mountain Bike

        9 |
        May 3, 2026 @ 1:09pm
        May 3, 2026
        12 |
        May 3, 2026 @ 1:09pm
        May 3, 2026
        11 |
        May 3, 2026 @ 1:09pm
        May 3, 2026
        report
        36 |
        Jul 22, 2024 @ 4:00pm
        Jul 22, 2024
        79 |
        May 21, 2023 @ 3:09pm
        May 21, 2023
        92 |
        May 8, 2023 @ 5:56pm
        May 8, 2023

        Recent Trail Reports

        Activity Feed

        usernameactiontypetitledate
        kwd42addreportactivity #94535174 and 6 more
        May 11, 2026 @ 7:33pm
        May 11, 2026
        ebrazellwishlisttrailactivity #94272259
        May 8, 2026 @ 6:20am
        May 8, 2026
        LeahShatkinwishlistrouteactivity #94192131
        May 6, 2026 @ 6:51pm
        May 6, 2026
        KeithfMWRIgaddphotoactivity #93976628 and 2 more
        May 3, 2026 @ 1:09pm
        May 3, 2026
        AndrewHallyaddreportactivity #93387763 and 9 more
        Apr 25, 2026 @ 1:31pm
        Apr 25, 2026

        Recent Comments

        usernametypetitlecommentdate
        mappermooktrailEscape VelocityLove the nice long stretch of slab riding at...
        Sep 20, 2025 @ 4:25pm
        Sep 20, 2025
        mappermooktrailGut BusterWith a consistent parade of smaller rock...
        Sep 20, 2025 @ 4:23pm
        Sep 20, 2025

        Nearby Areas

        namedistance
        Wharton Plantation 12 13 21.2 km
        Elbow Meadow 2 11.3 km
        Skitapet Conservation Land 7 21.9 km
        Picking Conservation Land East 12 km
        The Promised Land2.2 km

        Local Badges


        Activity Type Stats

        activitytypetrailsdistancedescentdescent distancetotal verticalratingglobal rankstate rankphotosreportsroutesridelogs
        Mountain Bike4013 miles1,276 ft6 miles223 ft
        #8,505#3,3207811915
        E-Bike1
        766
        Hike3613 miles1,276 ft6 miles223 ft
        #9,755#3,774811105
        Trail Running3613 miles1,276 ft6 miles223 ft
        #9,098#3,2558116
        Snowshoe84 miles423 ft2 miles141 ft
        #1,177#603124
        Nordic Ski84 miles423 ft2 miles141 ft
        #2,289#1,22511

        Frequently Asked Questions About Bear Hill

        What are the highest rated mountain biking trails in Bear Hill?
        The highest rated mountain biking trails in Bear Hill are: View all mountain biking trails sorted by rating.
        What is the best time of the year to ride in Bear Hill?
        Based on ride log data, the most popular months to ride in Bear Hill are:
        • November (4 activities)
        • December (2 activities)
        • January (2 activities)
        Check the Bear Hill reports page for current trail conditions, recent trail reports, and seasonal information from the local community.
        Where can I park to ride in Bear Hill?
        There are 3 parking locations listed in Bear Hill. The most popular parking spots are: View all parking and trailhead locations on the map to plan your visit.
        What is the longest trail in Bear Hill?
        The longest trail in Bear Hill is Beaver Crossing at 1.3 miles. View all trails sorted by distance.
        • By amcn & contributors
        • Admins: MV NEMBA
        • #51336 - 1,884 views

        Downloading of trail gps tracks in kml & gpx formats is enabled for Bear Hill.
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