more stats
2,031 ft
Distance
22 ft
Climb
-33 ft
Descent
00:03:14
Avg time
-11 ft
Altitude change
49 ft
Altitude min
72 ft
Altitude max
72 ft
Altitude start
59 ft
Altitude end
-0.5%
Grade
-7%
Grade max
7.8%
Grade min
604 ft
Distance climb
899 ft
Distance down
525 ft
Distance flat
00:03:14
Avg time

The Upside Details

  • Activities
    • Mountain Bike
    • Winter Fat Bike
    • Hike
    • Trail Running
    • Snowshoe
  • Riding Area
    Old Jail Lane / Hathaway's Pond
    Barnstable, Massachusetts
  • Difficulty Rating
  • Local Popularity
    95 in Mountain Biking [+]
    • 5 in Trail Running
    • 5 in Hiking
    • 5 in Snowshoeing
    • 5 in Winter Fat Biking
  • Global Ranking
    #184535 in Mountain Biking [+]
    • #384458 in Trail Running
    • #316289 in Hiking
    • #18427 in Snowshoeing
    • #38872 in Winter Fat Biking
  • State Ranking
    #3,368 in Mountain Biking · Massachusetts [+]
    • #13,142 in Trail Running
    • #11,522 in Hiking
    • #1,687 in Snowshoeing
    • #1,899 in Winter Fat Biking
  • Hiking SAC Scale
    T1 Hiking
  • Trail Type
    Singletrack
  • Bike Type
    XC, Fat
  • Direction
    Both Directions
  • Climb Difficulty
    Green
  • Physical Rating
    Easy
  • Trail Visibility
    Always easy to follow
  • Family Friendly
    Yes
  • Dogs Allowed
    Yes
  • eBike Allowed
  • Land Owner
    Town of Barnstable

No community description for The Upside trail has been added yet!

AI Generated Description

The Upside is a 2,031 ft popular green difficulty family friendly singletrack trail located near Barnstable Massachusetts. 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 3 minutes to complete this trail.

Tags
Family friendly

Local Trail Association

Traditionally Indigenous Territory

Recent Activity on Trail

Past Week
  • 0 rides
  •  
6 Months
  • 89 rides
  • 10 miles avg distance
All
  • 477 rides
  • Last: Oct 19, 2026
c1c2c3c4
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The Upside Trail Reports

statusdatedescription
Aug 23, 2026 @ 12:13pm (America/New_York)
Aug 23, 2026
Typical Cape trail, scrub oak, pine sand and couple small climbs
Jun 3, 2026 @ 11:09am (Pacific/Midway)
Jun 3, 2026
Mar 26, 2025 @ 10:34am
Mar 26, 2025
Cut n cleared
Feb 17, 2025 @ 2:16pm
Feb 17, 2025
8-In pine tree
Jan 1, 2025 @ 12:26pm
Jan 1, 2025
Big folding saw could take care of it
more »
Status:
on Aug 23, 2026
Ideal
no votes yet
Your vote: 0

view (1,381)
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      Directions to the-upside trailhead (41.685740, -70.308550)

      Photos

      3 more »
      report
      mtb
      54 |
      Mar 26, 2025 @ 10:34am
      Mar 26, 2025
      report
      mtb
      47 |
      Jan 1, 2025 @ 12:26pm
      Jan 1, 2025
      report
      hike
      38 |
      Feb 17, 2025 @ 2:16pm
      Feb 17, 2025

      Videos

      no videos have been added for The Upside yet, add a video.

      Routes with this trail

      38 miles • 2,284 ft • 50 • Point to Point •
      Leg #2 – Sandwich to Hyannis The second leg of this journey (and segment) starts as you pass the guard...
      30 miles • 1,412 ft • 34 • Point to Point •
      Leg #3 – Hyannis to Brewster The third leg in our trans-Cape endeavor starts in the parking lot of Cape...
      13 miles • 788 ft • 24 •
      This is the Formula U track for the Old Jail Lane Grand Prix

      Reviews / Comments

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      • By capedcod & contributors
      • #389712 - 534 views

      Frequently Asked Questions

      ▼ Where is The Upside located?
      The Upside is located in Old Jail Lane / Hathaway's Pond, Barnstable, Massachusetts, United States. It is part of the Old Jail Lane / Hathaway's Pond trail network. The trailhead is located at coordinates 41.68574, -70.30855.
      ▼ How hard is The Upside?
      The Upside is rated as Green difficulty. The physical rating is Easy. The average grade is 0.5%. The climb difficulty is rated Green.
      ▼ What is the elevation gain for The Upside?
      The Upside has 22 ft of elevation gain. The trail has 33 ft of elevation descent. The elevation ranges from 49 ft to 72 ft.
      ▼ Is The Upside a point to point trail?
      The Upside is not a point to point trail. The direction is Both Directions. The trail type is singletrack.
      ▼ How long is The Upside?
      The Upside is 2,031 ft long. The trail type is singletrack.
      ▼ Are dogs allowed on The Upside?
      Yes, dogs are allowed on The Upside. Please keep dogs on a leash where required and clean up after them.
      ▼ When is the best time of year to ride The Upside?
      Based on activity log data, the most popular months to ride The Upside are:
      • July (87 activities)
      • June (75 activities)
      • May (61 activities)
      Check the reports page for current trail conditions.
      ▼ How do I access The Upside? Where is the closest parking trailhead?
      The closest parking and trailhead locations to The Upside are: View all parking locations in the area.
      ▼ How long does it take to ride The Upside?
      Based on recorded activities, it takes an average of 3 minutes to ride The Upside. The trail is 2,031 ft long. Actual times will vary based on fitness level, conditions, and pace. View recent activity logs for more details.
      ▼ How busy is The Upside?
      The Upside is a very popular trail. There have been 1,287 recorded activities on this trail. The trail has received 1,381 check-ins. View recent activity on this trail.

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