Sheriff's Meadow Foundation Fourth Annual Trail Run, photo 1 of 7
Sheriff's Meadow Foundation Fourth Annual Trail Run, photo 2 of 7
Sheriff's Meadow Foundation Fourth Annual Trail Run, photo 3 of 7
Sheriff's Meadow Foundation Fourth Annual Trail Run, photo 4 of 7
Sheriff's Meadow Foundation Fourth Annual Trail Run, photo 5 of 7
Sheriff's Meadow Foundation Fourth Annual Trail Run, photo 6 of 7
Sheriff's Meadow Foundation Fourth Annual Trail Run, photo 7 of 7

Sheriff's Meadow Foundation Fourth Annual Trail Run

Edgartown, Massachusetts
Entry
$0
Day to register
1

At a glance

Date
Oct 24, 2026
Location
Edgartown, Massachusetts
Registration
Closes Oct 23, 2026, via runsignup.com

Listed from RunSignUp. Checked Oct 22, 2026.

Plan this race for free

Aid stations, cutoffs and pacing in one plan, with the timeline your crew follows. Crew invites and race-day updates come with a Race Pass.

Build my plan

About this race

Sheriff's Meadow Foundation welcomes you to its Fourth Annual Trail Run! The run will take place on Saturday, October 24th along the trails of Caroline Tuthill Preserve, an expanse of over 150 acres of oak and pitch pine forest, salt marsh, and open meadow located in Edgartown. Beginning at the field along Edgartown-Vineyard Haven Road, the trail run consists of a 3 mile loop through the pitch pine forest continuing on circuitous paths past salt marshes down to Sengekontacket Pond and back. The terrain begins in a field and includes a short section of paved bike path before entering the Preserve, where you will encounter a mix of sand and dirt paths before reaching a 160-foot raised boardwalk and ending back at the field.

* There is no cost to register for the event. Any contributions will support our work to conserve the natural, beautiful, rural landscape and character of Martha's Vineyard for present and future generations. 

Parking will be available at the Edgartown Park-and-Ride which is located by the Edgartown triangle and is free of charge. Please cross Edgartown-Vineyard Haven Road at the designated crosswalk and continue along the north side of the road to access the start line. Participants are encouraged to carpool or take public transportation if possible. Bus route schedules can be found here. If you are arriving from off-island please review the ferry schedules here. We are unable to provide transportation from the ferry terminals. 

Check in/ Bib pick up: There will be bib pickup on the day of the event at the Start/Finish area from 8:30 am to 9:30 am.

Key dates

Registration closes

Oct 23, 2026

Tomorrow

Race day

Oct 24, 2026

2d

Pricing

Current price

$0

Registration

Email me updates about Sheriff's Meadow Foundation Fourth Annual Trail Run

Registration openings and major changes, like a new date or a cancellation.

Entry transfers

Can't race, or need an entry? Post it here so nobody has to ask if it's still available.

Similar races

  • Powisset Farm Trail Run - Fall

    Oct 25Dover, MA8.6 mi, 5.6 mi +2

    71 mi from Sheriff's Meadow Foundation Fourth Annual Trail Run, similar trail technicality to Sheriff's Meadow Foundation Fourth Annual Trail Run, registration open

  • Upton 10.5K and Half Marathon Trail Race

    Nov 8Upton, MAHalf Marathon, 10.5K

    78 mi from Sheriff's Meadow Foundation Fourth Annual Trail Run, similar trail technicality to Sheriff's Meadow Foundation Fourth Annual Trail Run, registration open

  • Pumpkin Pacer 5k @ White Barn Farm

    Oct 24Wrentham, MA5K

    63 mi from Sheriff's Meadow Foundation Fourth Annual Trail Run, the same weekend as Sheriff's Meadow Foundation Fourth Annual Trail Run, registration open

Straight-line distance

All races in Massachusetts
All races near Boston
All October races
Race planning

Plan Sheriff's Meadow Foundation Fourth Annual Trail Run with Crewable

Build your aid station plan, organize your crew, and dial in your nutrition strategy. Everything you need to finish strong.

Build my plan

Are you the race director for Sheriff's Meadow Foundation Fourth Annual Trail Run?

Claim this race to manage registration, volunteers, and race day.

Claim your race