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Trail Conditions
- Unknown
- Snow Groomed
- Snow Packed
- Snow Covered
- Snow Cover Partial
- Freeze/thaw Cycle
- Icy
- Prevalent Mud
- Wet
- Variable
- Ideal
- Dry
- Very Dry
Trail Flow (Ridden Direction)
Trailforks scans users activity logs to determine the most popular direction each trail is ridden. A good flowing trail network will have most trails flowing in a single direction according to their intension.
The colour categories are based on what percentage of users are riding a trail in its intended direction.
The colour categories are based on what percentage of users are riding a trail in its intended direction.
- > 96%
- > 90%
- > 80%
- > 70%
- > 50%
- < 50%
- bi-directional trail
- no data
Trail Last Used
Trailforks scans activity logs to determine the last time a trail was ridden.
- < 2 days
- < 1 week
- < 2 weeks
- < 1 month
- < 6 months
- > 6 months
Trail Ridden Direction
The intended direction a trail should be ridden.
- Downhill Only
- Downhill Primary
- Both Directions
- Uphill Primary
- Uphill Only
- One Direction
Contribute Details
Colors indicate trail is missing specified detail.
- Description
- Photos
- Description & Photos
- Videos
Trail Popularity ?
Trailforks scans activity logs to determine which trails are ridden the most in the last 9 months.
Trails are compared with nearby trails in the same city region with a possible 25 colour shades.
Think of this as a heatmap, more activities = more kinetic energy = warmer colors.
- most popular
- popular
- less popular
- not popular
ATV/ORV/OHV Filter
Max Vehicle Width
inches
US Cell Coverage
Legend
Radar Time
Activity Recordings
Trailforks uses anonymized public activity data.
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Activity Recordings
Trailforks uses anonymized public activity data.
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Winter Trails
Warning
A routing network for winter maps does not exist. Selecting trails using the winter trails layer has been disabled.
Missing Trails
Most Popular
Least Popular
Trails are colored based on popularity. The more popular a trail is, the more red. Less popular trails trend towards green.
Jump Magnitude Heatmap
Heatmap of where users jump on trails. Zoom in to see individual jumps, click circles to view jump details.
BC Backroad Status
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Service Road Atlas is a free to use, community-driven service for viewing and creating reports on the numerous back-country service roads around B.C. and Alberta.
Slope Aspect
Direction the slope faces
Trails Deemphasized
Trails are shown in grey.
Only show trails with no bike usage.
Suggested Layers
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SaveWinchester 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, Gravel Biking, Winter Fat Biking, Snowshoeing and Adaptive Biking. Trails here are often faint trail, rocky and flowy. Scenery includes lakes and views. Common trail features include rock gardens, rock slabs and bridges. Many trails are family friendly. Popular destinations include Middlesex Fells Reservation, Whipple Hill and Fells.
This is an auto-generated description of Winchester.
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Trail info last updated
Activities Click to view
- Mountain Bike
233 trails
- Gravel Bike
111 trails
- Adaptive Bike
2 trails
- Winter Fat Bike
54 trails
- Hike
270 trails
- Trail Running
270 trails
- Snowshoe
23 trails
Region Details
- 90
- 3
- 36
- 89
- 14
- 1
Region Status
Open as of 16 hours
Stats
- Avg Trail Rating
- Trails (view details)
- 271
- Trails Mountain Bike
- 233
- Trails E-Bike
- 2
- Trails Gravel Bike
- 111
- Trails Adaptive Bike
- 2
- Trails Winter Fat Bike
- 54
- Trails Horse
- 3
- Trails Hike
- 270
- Trails Trail Running
- 270
- Trails Snowshoe
- 23
- Trails Backcountry Ski
- 1
- Trails Nordic Ski
- 1
- Total Distance
- 77 miles
- Total Descent
- 8,605 ft
- Total Vertical
- 328 ft
- Highest Trailhead
- 367 ft
- Reports
- 2,071
- Photos
- 117
- Completed Counter
- 97,107
Sub Regions
-
Fells
-
Middlesex Fells Reservation
- 3
- 27
- 75
- 9
-
Whipple Hill
- 6
- 14
- 5
Popular Winchester Mountain Biking Trails
• 95 ★ 0.0 • 4,006 ft • 82 ft • 3,012 •
Popular blue difficulty mixed. This multi-use trail can be used both directions and has a moderate overall physical rating with a 82 ft black diamond climb. Trail visibility is always easy to follow. On average it takes 7 minutes to complete this trail.
• 100 ★ 4.0 • 797 ft • 36 ft • 1,562 •
Popular blue difficulty singletrack. This multi-use trail can be used both directions and has a moderate overall physical rating with a 36 ft blue climb. Trail visibility is always easy to follow. On average it takes 1 minutes to complete this trail.
• 100 ★ 5.0 • 3,150 ft • 100 ft • 1,341 •
This section of trail is shared by the Skyline Trail, the as well as the Green Mountain bike Trail. Please be careful and give right of way to all pedestrians.
• 100 ★ 5.0 • 1,962 ft • 20 ft • 1,312 •
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. On average it takes 3 minutes to complete this trail.
• 100 ★ 4.4 • 4,846 ft • 49 ft • 1,163 •
Section exits Sheepfold near Sheepfold parking area then follows Chandler Rd for a brief piece before heading left (south) off Chandler Rd. Good ups and downs with some steep technical bony sections. Meets at and S. Dam Rd. intersection.
• 95 ★ 4.0 • 1 mile • 128 ft • 1,139 •
Many technical sections along this part of , a lot of small rock as well as rock face rollers. This is where you will find Orange Steps Rock Garden
• 95 ★ 4.0 • 322 ft • 0 ft • 1,070 •
Popular blue difficulty singletrack. This multi-use trail can be used both directions and has a moderate overall physical rating with a 0 ft green climb. It features bridge. On average it takes minutes to complete this trail.
• 95 ★ 5.0 • 4,131 ft • 100 ft • 1,038 •
Great section of (orange trail on DCR map). Starts at N. Border Rd., near Fallon Rd parking area. Loose gravel climb up , then flattens out. Drops right before trail hits Rd (main trail down from water tower) for good flowy downhill...
Winchester Mountain Bike Routes
★ 3.9 • 6 miles • 445 ft • 21 • Loop •
This route starts from the Bear Hill Parking Area at 100 Fallon Rd, Stoneham, MA (off exit 35 Route 93)....
★ 5.0 • 9 miles • 601 ft • 18 •
Greater Boston chapter of New England Mountain Biking Association route for our Fells season opener event....
★ 4.0 • 7 miles • 524 ft • 36 • Loop •
The Green Mountain Bike Route (Green Blazes) is a relatively easy 6.4 mile loop around the North, Middle...
★ 1.0 • 11 miles • 770 ft • 22 • Loop •
Greater Boston chapter of New England Mountain Biking Association route for our Fells season opener event....
★ 4.0 • 9 miles • 649 ft • 53 •
2019 Fells MBAS event white arrowed course, organized by GBNEMBA
5 miles • 202 ft • 7 •
Greater Boston chapter of New England Mountain Biking Association route for our Fells season opener event....
Photos of Winchester Mountain Bike
Videos of Winchester Mountain Bike
mtb
18:57 |
85 |
Jul 3, 2025
mtb
4:37 |
957 |
Aug 28, 2018
Current Trail Warnings
| status | trail | date | condition | user | info |
|---|---|---|---|---|---|
| Reservoir Trail Molly's to Middle Res Rd | Oct 2, 2026 @ 8:33am (America/New_York) 16 hours | Variable | Deathmetalhead | ||
| B5.10 to C5.14 | Oct 2, 2026 @ 7:34am (America/New_York) 17 hours | Variable | Deathmetalhead | ||
| Gate 19 Access Trail | Sep 11, 2026 @ 7:54am (America/New_York) Sep 11, 2026 | Dry | Deathmetalhead |
Recent Trail Reports
Activity Feed
| username | action | type | title | date |
|---|---|---|---|---|
| Deathmetalhead | add | report | activity #105029378 and 1 more | Oct 2, 2026 @ 4:34am 17 hours |
| magic71 | update | trail | activity #104459602 | Sep 23, 2026 @ 5:56pm Sep 23, 2026 |
| bobg13 | add | trail | activity #104458891 | Sep 23, 2026 @ 5:44pm Sep 23, 2026 |
| AndrewHally | add | report | activity #104445563 and 12 more | Sep 23, 2026 @ 2:14pm Sep 23, 2026 |
| PetertTCmdg | wishlist | route | activity #104143776 and 1 more | Sep 19, 2026 @ 11:13am Sep 19, 2026 |
Recent Comments
| username | type | title | comment | date |
|---|---|---|---|---|
| trail | Per DCR, isn’t no mountain biking allowed... | May 28, 2026 @ 12:22pm May 28, 2026 | ||
| trail | Looped clockwise so fun! Finally completed... | Sep 2, 2025 @ 1:41pm Sep 2, 2025 | ||
| trail | Sketchy enterance off the street but levels out | Mar 16, 2025 @ 3:02pm Mar 16, 2025 | ||
| trail | Chunky downhill from the east or technical... | Mar 8, 2024 @ 12:30pm Mar 8, 2024 | ||
| trail | Fun rock roll down red to green (NE->SW) | Mar 8, 2024 @ 12:24pm Mar 8, 2024 |
Local Badges
-
10 Green Trails405 awarded -
10 Blue Trails1,050 awarded -
Epic Ride Climb 2k5 awarded -
Climbing 10k Badge175 awarded -
Climbing 100k Badge6 awarded -
Epic Ride Descent 2k4 awarded
Activity Type Stats
| activitytype | trails | distance | descent | descent distance | total vertical | rating | global rank | state rank | photos | reports | routes | activity logs |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Mountain Bike | 233 | 68 miles | 7,031 ft | 27 miles | 328 ft | #225 | #4 | 114 | 2,071 | 10 | 50,341 | |
| E-Bike | 2 | 974 ft | 3 ft | 315 ft | 3 ft | 1,683 | 276 | |||||
| Gravel Bike | 111 | 39 miles | 2,913 ft | 14 miles | 318 ft | #1,485 | #8 | 170 | 190 | |||
| Adaptive Bike | 2 | 1,112 ft | 69 ft | #7,672 | #107 | 6 | ||||||
| Winter Fat Bike | 54 | 13 miles | 1,056 ft | 5 miles | 322 ft | #1,862 | #14 | 5 | 6 | |||
| Horse | 3 | 2 miles | 177 ft | 4,075 ft | 105 ft | 684 | 1 | |||||
| Hike | 270 | 76 miles | 8,589 ft | 30 miles | 328 ft | #1,378 | #19 | 3 | 2,071 | 2 | 2,912 | |
| Trail Running | 270 | 76 miles | 8,589 ft | 30 miles | 328 ft | #918 | #13 | 2,071 | 2 | 3,942 | ||
| Snowshoe | 23 | 4 miles | 364 ft | 2 miles | 249 ft | #1,019 | #68 | 10 | 1 | 30 | ||
| Backcountry Ski | 1 | 974 ft | 3 ft | 315 ft | 3 ft | 24 | ||||||
| Nordic Ski | 1 | 974 ft | 3 ft | 315 ft | 3 ft | 77 |
Frequently Asked Questions
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What are the best places to ride in Winchester?
Winchester has 3 areas to explore for mountain biking. The top rated areas are:
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What are the highest rated mountain biking trails in Winchester?
The highest rated mountain biking trails in Winchester are:
- Reservoir Trail Money Hill section (4.3/5)
- Whipped Climb (4.2/5)
- Bear Hill DH 2 (4.1/5)
- Reservoir Trail (Dike Road to Sheepfold) (4.1/5)
- Main Shared Trail (4.1/5)
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What is the best time of the year to ride in Winchester?
Based on activity log data, the most popular months to ride in Winchester are:
- June (985 activities)
- May (866 activities)
- August (820 activities)
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Where can I park to ride in Winchester?
There are 9 parking locations listed in Winchester. The most popular parking spots are:
- Parking
- Bear Hill Parking lot (100 Fallon Rd, Stoneham, MA, off Exit 35 Rt. 93)
- Parking lot on S.Border Rd., near S. Dam Rd.,
- Lynn Woods - Jeep Kelly Parking
- Whipple Hill Parking Lot
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What is the longest trail in Winchester?
The longest trail in Winchester is Reservoir Trail Molly's to Middle Res Rd at 1.0 mile. View all trails sorted by distance.
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What are the best & highest rated hiking trails in Winchester?
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What are the best & highest rated trail running trails in Winchester?
The best trail running trails in Winchester are:
- Skyline Trail C2-6 to D3-1
- Cross Fells Trail (C5-18 to C5-11)
- Summer-Lowell Entry
- Main Shared Trail
- Reservoir Trail
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How many trails are in Winchester?
Winchester has a total of 271 trails. Of those, 233 are designated for mountain biking. Browse top mountain biking trails in Winchester to find detailed information including difficulty ratings, distances, and trail conditions.
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Which trail has the most elevation gain in Winchester?
The trail with the most elevation gain in Winchester is Cross Fells Trail Middle Section with 129 ft of elevation gain. View all trails sorted by elevation gain.
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Which trail has the most elevation descent in Winchester?
The trail with the most elevation descent in Winchester is Crystal Spring Trail (Whip Hill Path to Pond St.) with 169 ft of elevation descent. View all trails sorted by elevation descent.
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What activities are most popular in Winchester?
Winchester supports the following activities: Mountain Biking, Gravel Biking, Adaptive Biking, Winter Fat Biking, Hiking, Trail Running, Snowshoeing.
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What are the steepest mountain biking trails in Winchester?
The steepest mountain biking trail in Winchester is Cristal Spring Trail Ending with an average grade of 13.7%. View all trails sorted by grade.
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Are there any trails with scenic viewpoints in Winchester?
Yes, there are 5 scenic viewpoints marked along trails in Winchester. Some popular viewpoints include: Explore more points of interest to find trails with the best views.
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What trails have the biggest jumps in Winchester?
The trails with the biggest jumps in Winchester are: Browse all mountain bike trails to find trails with jumps and technical features.
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Are the trails open in Winchester?
The overall region status for Winchester is Clear / Green. Out of 236 trails:
- Clear / Green: 214
- Minor Issue / Yellow: 13
- Significant Issue / Amber: 8
- Closed: 1
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What are the trail conditions in Winchester?
Based on trail reports from the past week in Winchester:
- Dry: 13 trails
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Can I ride an ebike in Winchester?
There are 1 trails in Winchester that allow e-bikes. Check the e-bike trails listing for specific trail access details and any local regulations.
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What are the most popular mountain biking routes in Winchester?
The most popular mountain biking routes in Winchester are: View all mountain biking routes in Winchester.
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What type of bike is most common in Winchester?
Based on activity log data, the most common bike types used in Winchester are:
- AM (544 activities)
- XC (57 activities)
- Trials (16 activities)
- RD (1 activities)
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What are the most popular Strava Segments in Winchester?
The most popular Strava segments in Winchester are:
- Pretty Fun for a Fire Road (3,488 athletes)
- *The* gulch (3,171 athletes)
- BIG LEAGUE ROCK-N-ROLL (3,144 athletes)
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What are some popular technical trail features in Winchester?
There are 11 technical trail features (TTFs) in Winchester. Some popular features include:
- Big ol' Rock (Rock Face)
- Orange Steps Rock Garden (Rock Garden)
- TTF (Drop)
- Slip'n'slide Rock (Rock Face)
- Three Bastards (Rock Garden)
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What trails are closed in Winchester?
There are currently 1 closed trails in Winchester. The breakdown of all trail statuses is:
- Clear / Green: 214
- Minor Issue / Yellow: 13
- Significant Issue / Amber: 8
- Closed: 1
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Are there accessible or adaptive trails in Winchester?
Yes, there are 2 accessible/adaptive trails in Winchester. View all adaptive trails in Winchester for specific accessibility information.
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What are the most popular mountain biking trails in Winchester?
The most popular mountain biking trails in Winchester are:
- Bear Hill DH 2
- Bear Hill DH
- Reservoir Trail Money Hill section
- Reservoir Trail (Sheepfold to E. Dam Rd.)
- Sheepfold Path
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What are the best beginner ride trails in Winchester?
The best beginner mountain biking trails in Winchester are:
- Sheepfold Path (4/5)
- Fire Road (2/5)
- Farm / Wetland Yellow (1/5)
Activities
Trails
- By peloquin & contributors
- Admins: GB NEMBA, BCT
- #5535 - 6,117 views
- winchester activity log | embed map of Winchester mountain bike trails | winchester mountain biking points of interest polygons
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