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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.

      Trail info last updated

      Activities Click to view
      Region Details
      • 3
      • 10
      • 22
      • 2

      Region Status
      Open as of 2 days
      Local Trail Association

      Stats

      Avg Trail Rating
      Trails (view details)
      37
      Trails Mountain Bike
      37
      Trails E-Bike
      1
      Trails Gravel Bike
      8
      Trails Winter Fat Bike
      1
      Trails Hike
      35
      Trails Trail Running
      35
      Trails Snowshoe
      8
      Trails Nordic Ski
      8
      Total Distance
      17 miles
      Total Descent Distance
      7 miles
      Total Descent
      1,719 ft
      Total Vertical
      223 ft
      Highest Trailhead
      410 ft
      Reports
      79
      Photos
      6
      Completed Counter
      2,112

      Popular Bear Hill Mountain Biking Trails

      80 2.5 2,323 ft 22 ft 223
      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.
      70 0.0 3,320 ft 53 ft 126
      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.
      100 4.0 2,500 ft 53 ft 116
      Popular blue difficulty singletrack. This mountain bike primary trail can be used both directions. On average it takes 5 minutes to complete this trail.
      95 5.0 427 ft 0 ft 91
      A couple of nice rock rolls
      90 5.0 2,690 ft 8 ft 89
      Technical singletrack with a descent down .
      100 0.0 2,595 ft 5 ft 88
      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.
      85 0.0 922 ft 0 ft 82
      Trail on top of the old berms that were made as part of the quarry.
      95 0.0 1,125 ft 58 ft 82
      This single track heads up to the quarry from Rd. without taking dirt roads

      Recent Ride Log Activity in Region

      Today
      • 0 rides
      Yesterday
      • 0 rides
      Past Week
      • 5 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

      mtb
      17 |
      May 3, 2026 @ 1:09pm
      May 3, 2026
      mtb
      23 |
      May 3, 2026 @ 1:09pm
      May 3, 2026
      mtb
      19 |
      May 3, 2026 @ 1:09pm
      May 3, 2026
      mtb
      89 |
      May 21, 2023 @ 3:09pm
      May 21, 2023
      mtb
      99 |
      May 8, 2023 @ 5:56pm
      May 8, 2023
      report
      mtb
      43 |
      Jul 22, 2024 @ 4:00pm
      Jul 22, 2024

      Current Trail Warnings

      statustraildateconditionuserinfo
      Haystack
      Sep 16, 2026 @ 7:54pm (America/New_York)
      2 days
      Very DrypanduOvergrown vegetation

      Recent Trail Reports

      Activity Feed

      usernameactiontypetitledate
      panduaddreportactivity #103950822 and 1 more
      Sep 16, 2026 @ 4:55pm
      2 days
      Bpagsmtbwishlistregionactivity #103405151
      Sep 9, 2026 @ 5:49am
      Sep 9, 2026
      dviratiswishlistregionactivity #103253994
      Sep 7, 2026 @ 6:21am
      Sep 7, 2026
      Dtrunfioriddentrailactivity #100622181
      Aug 2, 2026 @ 5:33pm
      Aug 2, 2026
      kwd42addreportactivity #94535174 and 6 more
      May 11, 2026 @ 7:33pm
      May 11, 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 rankphotosreportsroutesactivity logs
      Mountain Bike3717 miles1,719 ft7 miles223 ft
      #8,429#3,2606791925
      E-Bike11,440 ft26 ft679 ft26 ft
      7220
      Gravel Bike84 miles171 ft2 miles217 ft
      4
      Winter Fat Bike11,506 ft16 ft302 ft62 ft
      Hike3516 miles1,683 ft7 miles223 ft
      #9,522#3,57379188
      Trail Running3516 miles1,683 ft7 miles223 ft
      #8,907#3,1057916
      Snowshoe84 miles512 ft2 miles194 ft
      #1,342#702223
      Nordic Ski84 miles512 ft2 miles194 ft
      #2,363#1,24622

      Frequently Asked Questions

      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 activity log data, the most popular months to ride in Bear Hill are:
      • May (37 activities)
      • August (25 activities)
      • April (23 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.
      What are the best & highest rated hiking trails in Bear Hill?
      What are the best & highest rated trail running trails in Bear Hill?
      How many trails are in Bear Hill?
      Bear Hill has a total of 37 trails. Browse top mountain biking trails in Bear Hill to find detailed information including difficulty ratings, distances, and trail conditions.
      Which trail has the most elevation gain in Bear Hill?
      The trail with the most elevation gain in Bear Hill is Quarry Loop with 154 ft of elevation gain. View all trails sorted by elevation gain.
      Which trail has the most elevation descent in Bear Hill?
      The trail with the most elevation descent in Bear Hill is Beaver Crossing with 191 ft of elevation descent. View all trails sorted by elevation descent.
      What activities are most popular in Bear Hill?
      Bear Hill supports the following activities: Mountain Biking, Hiking, Trail Running, Snowshoeing, Nordic Skiing.
      What are the steepest mountain biking trails in Bear Hill?
      The steepest mountain biking trail in Bear Hill is Big Ups with an average grade of 6.2%. View all trails sorted by grade.
      Are the trails open in Bear Hill?
      The overall region status for Bear Hill is Clear / Green. Out of 27 trails:
      • Clear / Green: 24
      • Minor Issue / Yellow: 2
      • Significant Issue / Amber: 1
      View the full trail status page for the latest updates.
      What are the trail conditions in Bear Hill?
      Based on trail reports from the past week in Bear Hill:
      • Ideal: 1 trail
      • Very Dry: 1 trail
      Check the Bear Hill trail status page for the most current conditions and recent trail reports.
      Can I ride an ebike in Bear Hill?
      There are 1 trails in Bear Hill that allow e-bikes. Check the e-bike trails listing for specific trail access details and any local regulations.
      What are the most popular mountain biking routes in Bear Hill?
      The most popular mountain biking routes in Bear Hill are: View all mountain biking routes in Bear Hill.
      What type of bike is most common in Bear Hill?
      Based on activity log data, the most common bike types used in Bear Hill are:
      • AM (35 activities)
      • Trials (11 activities)
      • XC (3 activities)
      Check the Bear Hill activity logs for more details.
      What are the most popular Strava Segments in Bear Hill?
      The most popular Strava segments in Bear Hill are:
      • Sprint to Cow Pond Bridge (360 athletes)
      • Roger's 30-pack Challenge (326 athletes)
      • Escker S to N (261 athletes)
      View all Strava segments in Bear Hill.
      What are some popular technical trail features in Bear Hill?
      There are 4 technical trail features (TTFs) in Bear Hill. Some popular features include: View all technical trail features in Bear Hill.
      What are the most popular mountain biking trails in Bear Hill?
      What are the best beginner ride trails in Bear Hill?
      The best beginner mountain biking trails in Bear Hill are: View all beginner mountain biking trails in Bear Hill.
      • By amcn & contributors
      • Admins: MV NEMBA
      • #51336 - 2,167 views

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