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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

      Activities Click to view
      Region Details
      • 17
      • 2
      • 66
      • 37
      • 5
      • 2

      Region Status
      Open as of 12 hours
      Local Trail Association

      Trail Running Stats

      Global Ranking
      #3,289
      State Ranking
      #4
      Trails (view details)
      129
      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
      60 miles
      Total Descent Distance
      22 miles
      Total Descent
      3,855 ft
      Total Vertical
      197 ft
      Reports
      1,796
      Photos
      1
      Completed Counter
      349

      Sub Regions

      Popular Westerly Trail Running Trails

      • 90 ★ 4.4 • 1,503 ft • 81 ft • 12 •
      Main Street is the primary artery from the pond to most of the trails. This is the existing legacy trail through the property. It has two really steep rollers at the top of Little Sumpthin - left and right - the left only hit when dry,...
      • 100 ★ 4.4 • 968 ft • 0 ft • 9 •
      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 • 2 miles • 57 ft • 9 •
      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...
      • 75 ★ 4.8 • 4,085 ft • 89 ft • 8 •
      Leaning Chimney is rated overall Blue, but it is a tough trail due to a number of punch climbs. It is a beatiful trail going up and around a forested ridge line and across a seasonal brook. Features abound that include a triple huck...
      • 95 ★ 4.9 • 3,373 ft • 36 ft • 7 •
      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...
      • 80 ★ 4.6 • 3 miles • 224 ft • 7 • • mtb
      Little Sister is by far the most difficult trail in Woody Hill. It is a trail that is not for everyone. The true distance is 4.29 miles and contains about every conceivable feature for southern Rhode Island from a severe ridge line that...
      • 70 ★ 4.0 • 4,770 ft • 136 ft • 7 •
      One half of the Westerly School System X-C running trail- start at the back corner of the south Lacrosse Field, turn left and begin climbing past the junctions of "Weathering Steel" and the "Middle School Connector". Ends at the top of...
      • 95 ★ 4.0 • 807 ft • 11 ft • 7 •
      Hazy Day is an old fishermans trail that was re-purposed for mountain biking. It is a short trail, but you gets off Main Street. The original trail actually connected to West Main Street (bottom of Pour Judgement), but that section is...

      Recent Run Log Activity in Region

      Today

      • 0 trail runs

      Yesterday

      • 0 trail runs
      Past Week
      • 1 trail runs

      Photos of Westerly

      report
      trailrun
      95 |
      Oct 27, 2023 @ 11:27am
      Oct 27, 2023
      report
      hike
      73 |
      May 24, 2025 @ 8:25am
      May 24, 2025
      report
      snowshoe
      85 |
      Jan 30, 2022 @ 10:46am
      Jan 30, 2022
      mtb
      55 |
      Jun 4, 2026 @ 4:23am
      Jun 4, 2026
      mtb
      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

      Videos of Westerly

      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 | 225 | Apr 30, 2026
      Mountain Biking Woody Hill, Hop Boogie, The...
      mtb
      trail: Hop Boogie
      6:23 | 430 | Jul 27, 2023 , Westerly
      Little Sister is the Best Trail at Woody Hill
      mtb
      11:43 | 1532 | Aug 17, 2021 , Westerly
      Woody Hill Highlight Trail Review
      mtb
      6:12 | 956 | Jul 20, 2021 , Westerly

      Recent Trail Reports

      Activity Feed

      usernameactiontypetitledate
      DICKSTARaddreportactivity #107799636
      Nov 14, 2026 @ 4:23pm
      2 hours
      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

      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#32471,8262320,164
      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
      1583
      Hike12960 miles3,855 ft22 miles197 ft
      #3,129#811,801881
      Trail Running12960 miles3,855 ft22 miles197 ft
      #3,289#411,796384
      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 run in Westerly?
      ▼ What are the highest rated trail running trails in Westerly?
      The highest rated trail running trails in Westerly are: View all trail running trails sorted by rating.
      ▼ Where can I park to run 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?
      ▼ How many trails are in Westerly?
      Westerly has a total of 130 trails. Of those, 129 are designated for trail running. Browse top trail running 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 are the steepest trail running trails in Westerly?
      The steepest trail running trail in Westerly is Yellow Trail with an average grade of 12.2%. 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.
      ▼ Are the trails open in Westerly?
      The overall region status for Westerly is Clear / Green. Out of 92 trails:
      • Clear / Green: 78
      • Minor Issue / Yellow: 5
      • Significant Issue / Amber: 9
      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 top sights to see 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 trail running trails in Westerly?
      ▼ What are the best beginner trail run trails in Westerly?
      The best beginner trail running trails in Westerly are: View all beginner trail running trails in Westerly.
      • By butters & contributors
      • Admins: RI NEMBA, AMC-NARR, newforesttherapy, PlumbBobM
      • #21504 - 6,661 views

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