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      Westerly trails and routes are listed on Trailforks with interactive trail maps, difficulty ratings, photos, and user-reported trail conditions. The Trailforks community has mapped hundreds of trails and shared hundreds of photos in this region. Supported activity types include Hiking, Trail Running, Mountain Biking, Snowshoeing, Winter Fat Biking, Nordic Skiing and Adaptive Biking. Trails here are often faint trail and flowy. Scenery includes ridgelines. Common trail features include rock slabs, rock gardens and drops. Amenities include cafes. Popular destinations include Woody Hill, Grills Preserve and Grills Wildlife Sanctuary and Riverwood Preserve.
      This is an auto-generated description of Westerly. Login or register to submit a custom description.

      Trail info last updated

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      Region Details
      • 16
      • 2
      • 52
      • 32
      • 6
      • 2

      Region Status
      Open as of Nov 8, 2026
      Local Trail Association

      Stats

      Avg Trail Rating
      Trails (view details)
      130
      Trails Mountain Bike
      110
      Trails Gravel Bike
      47
      Trails Adaptive Bike
      1
      Trails Winter Fat Bike
      32
      Trails Horse
      1
      Trails Hike
      129
      Trails Trail Running
      129
      Trails Snowshoe
      79
      Trails Nordic Ski
      31
      Total Distance
      61 miles
      Total Descent
      3,871 ft
      Total Vertical
      196 ft
      Highest Trailhead
      219 ft
      Reports
      1,825
      Photos
      249
      Completed Counter
      43,182

      Sub Regions

      Popular Westerly Mountain Biking Trails

      • 100 ★ 4.4 • 968 ft • 0 ft • 1,250 •
      Flying Jenny was the second trail built and basically became a connector trail from North Main Street to Hobbit Juice. This trail has a few short rock gardens with off-camber turns into rocks for added fun. At the end there is a huge...
      • 95 ★ 4.5 • 4,452 ft • 6 ft • 1,249 •
      Highly rated popular green difficulty singletrack. This multi-use trail can be used downhill primary and has a moderate overall physical rating with a 6 ft blue climb. Trail visibility is always easy to follow. On average it takes 5 minutes to complete this trail.
      • 100 ★ 4.5 • 1 mile • 81 ft • 1,221 •
      Naughty Nurse is a beginner friendly trail that meanders through the forest. It has 9 stone wall crossings that can either be rolled or hucked. This trail is also 'trike' adapted for disabled riders to enjoy. There is also a ladder ramp...
      • 100 ★ 4.5 • 3,711 ft • 17 ft • 1,172 •
      Hansel & Gretel (also known as Soft Serve) is a great trail that goes through one of the only Pine Forests within Woody Hill. This is a legacy trail built by the local trail running group. It has a few rock rollers, sharp turns and...
      • 100 ★ 4.7 • 4,488 ft • 45 ft • 1,172 •
      Hobbit Juice is simply a super fast mostly downhill trail. It starts at the intersection of Flying Jenny and Little Sister and the first section can just be ripped. the middle section has a short, steep punch climb followed by a...
      • 95 ★ 4.9 • 3,373 ft • 36 ft • 1,118 •
      Yo Mama is a short, super fun trail that was built to get off the cart roads from the lacrosse fields to the main body of trails. It crosses North Main Street at a technical ridge line. The first section has a steep roller (meaning...
      • 100 ★ 4.5 • 2 miles • 57 ft • 1,117 •
      Driving Miss Hazy is a beginner specific trail done at the request of the local high school mountain bike team for the new kids to delevop skills and stamina. It is not a difficult trail by any means, but does have numerous 'things' for...
      • 95 ★ 4.6 • 1 mile • 64 ft • 1,041 •
      Alter Ego is my favorite trail in Woody Hill and is one of the very few trails that built itself - the entire trail was flagged out and built in one take. The trail goes behind both Hobbit Juice and Naughty Nurse and is basically a big...

      Recent Ride Log Activity in Region

      Today

      • 3 rides

      Yesterday

      • 11 rides
      Past Week
      • 58 rides

      Westerly Mountain Bike Routes

      ★ 2.0 • 20 miles • 1,429 ft • 27 •
      This is the expert route for the 2024 Woody Hill Fun Ride.
      14 miles • 928 ft • 22 •
      This is the RINEMBA 2024 Woody Hill Fun Ride Intermediate Loop
      ★ 1.0 • 7 miles • 360 ft • 5 •
      This is the mellow loop for the RINEMBA 2024 Woody Hill Fun Ride
      ★ 4.0 • 16 miles • 981 ft • 23 •
      This is the beginner/relaxed loop for the 2023 Woody Hill Fun Ride
      10 miles • 484 ft • 10 •
      Nice tour of the area. All features are optional. No big climbs, but if you pour on the gas it gets real...
      ★ 2.0 • 22 miles • 1,696 ft • 31 •
      This is the expert loop from the 2025 Woody Hill Fun Ride

      Photos of Westerly Mountain Bike

      mtb
      55 |
      Jun 4, 2026 @ 4:23am
      Jun 4, 2026
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      64 |
      Jun 4, 2026 @ 4:17am
      Jun 4, 2026
      mtb
      122 |
      Oct 18, 2025 @ 10:35am
      Oct 18, 2025
      mtb
      170 |
      Oct 18, 2025 @ 10:35am
      Oct 18, 2025
      mtb
      143 |
      Oct 18, 2025 @ 10:35am
      Oct 18, 2025
      mtb
      120 |
      Oct 18, 2025 @ 10:29am
      Oct 18, 2025
      mtb
      103 |
      Oct 18, 2025 @ 10:29am
      Oct 18, 2025
      mtb
      116 |
      Oct 18, 2025 @ 10:29am
      Oct 18, 2025
      mtb
      109 |
      Oct 18, 2025 @ 9:55am
      Oct 18, 2025
      mtb
      127 |
      Oct 18, 2025 @ 9:37am
      Oct 18, 2025
      mtb
      116 |
      Oct 18, 2025 @ 9:37am
      Oct 18, 2025
      mtb
      110 |
      Feb 4, 2025 @ 6:10pm
      Feb 4, 2025

      Videos of Westerly Mountain Bike

      First Snow 2021
      mtb
      9:33 | 198 | Dec 11, 2021
      mtb
      0:08 | | Aug 14, 2021
      Little Sister skinny send
      mtb
      0:05 | | Jul 8, 2021
      Woody Hill drop
      mtb
      0:07 | 736 | Apr 2, 2021
      4 Hours in Woody Hill, Training for a 200km...
      mtb

      7:13 | 224 | Apr 30, 2026
      Mountain Biking Woody Hill, Hop Boogie, The...
      mtb
      trail: Hop Boogie
      6:23 | 429 | Jul 27, 2023 , Westerly
      Little Sister is the Best Trail at Woody Hill
      mtb
      11:43 | 1531 | Aug 17, 2021 , Westerly
      Woody Hill Highlight Trail Review
      mtb
      6:12 | 955 | Jul 20, 2021 , Westerly

      Recent Trail Reports

      Activity Feed

      usernameactiontypetitledate
      jtroutaddreportactivity #107463078
      Nov 8, 2026 @ 3:21pm
      Nov 8, 2026
      dgallupaddkarmaactivity #107423209
      Nov 8, 2026 @ 7:14am
      Nov 8, 2026
      Jbdaukasaddreportactivity #106928582 and 1 more
      Oct 31, 2026 @ 8:21am
      Oct 31, 2026
      timsabaddreportactivity #106862429 and 2 more
      Oct 30, 2026 @ 7:38am
      Oct 30, 2026
      Dekka-Ducotewishlistregionactivity #106745849
      Oct 28, 2026 @ 7:37am
      Oct 28, 2026

      Recent Comments

      usernametypetitlecommentdate
      gbtourtrailFern DriveYes, you just park along the right side of the...
      Aug 3, 2026 @ 5:27am
      Aug 3, 2026
      kmacglaflintrailFern DriveIs there parking here? Looking to access Miss Hazy
      Jul 7, 2026 @ 4:52am
      Jul 7, 2026
      eric65reportDriving Miss HazyThe picture shows my activity as Dirtbike but...
      Jul 5, 2026 @ 4:31pm
      Jul 5, 2026
      duncan-dotrailWoody Hill RoadNnnn
      May 19, 2026 @ 8:34am
      May 19, 2026
      duncan-dotrailWoody Hill Road5-19-26
      May 19, 2026 @ 8:34am
      May 19, 2026

      Local Badges


      Activity Type Stats

      activitytypetrailsdistancedescentdescent distancetotal verticalratingglobal rankstate rankphotosreportsroutesactivity logs
      Mountain Bike11052 miles3,133 ft19 miles187 ft
      #596#32421,8252320,158
      Gravel Bike4720 miles1,086 ft7 miles164 ft
      #327#1709692
      Adaptive Bike11,047 ft30 ft827 ft33 ft
      #6,879#81011
      Winter Fat Bike3217 miles1,155 ft6 miles174 ft
      #1,326#37520
      Horse11,529 ft7 ft417 ft43 ft
      1573
      Hike12960 miles3,855 ft22 miles197 ft
      #3,129#811,800881
      Trail Running12960 miles3,855 ft22 miles197 ft
      #3,289#411,795384
      Snowshoe7941 miles2,100 ft14 miles187 ft
      #466#2131622
      Nordic Ski3118 miles745 ft5 miles157 ft
      #1,036#5428

      Frequently Asked Questions

      ▼ What are the best places to ride in Westerly?
      ▼ What are the highest rated mountain biking trails in Westerly?
      The highest rated mountain biking trails in Westerly are: View all mountain biking trails sorted by rating.
      ▼ Where can I park to ride in Westerly?
      There are 11 parking locations listed in Westerly. 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 Westerly?
      The longest trail in Westerly is Little Sister at 3.0 miles. View all trails sorted by distance.
      ▼ What are the best & highest rated hiking trails in Westerly?
      ▼ What are the best & highest rated trail running trails in Westerly?
      ▼ How many trails are in Westerly?
      Westerly has a total of 130 trails. Of those, 110 are designated for mountain biking. Browse top mountain biking trails in Westerly to find detailed information including difficulty ratings, distances, and trail conditions.
      ▼ Which trail has the most elevation gain in Westerly?
      The trail with the most elevation gain in Westerly is Little Sister with 224 ft of elevation gain. View all trails sorted by elevation gain.
      ▼ Which trail has the most elevation descent in Westerly?
      The trail with the most elevation descent in Westerly is Little Sister with 271 ft of elevation descent. View all trails sorted by elevation descent.
      ▼ What activities are most popular in Westerly?
      Westerly supports the following activities: Mountain Biking, Adaptive Biking, Winter Fat Biking, Hiking, Trail Running, Snowshoeing, Nordic Skiing.
      ▼ What bike services are there in Westerly?
      The following bike services are available in Westerly:
      • Bike Shop (2)
      Browse the full Westerly directory for details.
      ▼ What are the steepest mountain biking trails in Westerly?
      The steepest mountain biking trail in Westerly is Cart Road Connector with an average grade of 7.6%. View all trails sorted by grade.
      ▼ Are there any trails with scenic viewpoints in Westerly?
      Yes, there are 1 scenic viewpoints marked along trails in Westerly. Some popular viewpoints include: Explore more points of interest to find trails with the best views.
      ▼ What trails have the biggest jumps in Westerly?
      The trails with the biggest jumps in Westerly are: Browse all mountain bike trails to find trails with jumps and technical features.
      ▼ Are the trails open in Westerly?
      The overall region status for Westerly is Clear / Green. Out of 93 trails:
      • Clear / Green: 77
      • Minor Issue / Yellow: 6
      • Significant Issue / Amber: 10
      View the full trail status page for the latest updates.
      ▼ What are the trail conditions in Westerly?
      Based on trail reports from the past week in Westerly:
      • Variable: 1 trail
      Check the Westerly trail status page for the most current conditions and recent trail reports.
      ▼ What are the most popular mountain biking routes in Westerly?
      ▼ What are the top sights to see in Westerly?
      ▼ What are the most popular Strava Segments in Westerly?
      The most popular Strava segments in Westerly are:
      • Driving Miss Hazy (1,267 athletes)
      • Little Sister (1,215 athletes)
      • Hoppin and Boogyin (1,180 athletes)
      View all Strava segments in Westerly.
      ▼ What are some popular technical trail features in Westerly?
      There are 72 technical trail features (TTFs) in Westerly. Some popular features include: View all technical trail features in Westerly.
      ▼ Are there accessible or adaptive trails in Westerly?
      Yes, there are 1 accessible/adaptive trails in Westerly. View all adaptive trails in Westerly for specific accessibility information.
      ▼ Are there local clubs or events in Westerly?
      There are 1 local clubs or associations listed in the Westerly directory. Browse the local directory for details.
      ▼ What are the most popular mountain biking trails in Westerly?
      ▼ What are the best beginner ride trails in Westerly?
      The best beginner mountain biking trails in Westerly are: View all beginner mountain biking trails in Westerly.
      • By butters & contributors
      • Admins: RI NEMBA, AMC-NARR, newforesttherapy, PlumbBobM
      • #21504 - 6,645 views

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