Upcoming trail races in Massachusetts

30 trail races are coming up in Massachusetts, out of 332 races on the statewide calendar. Compare dates, distances and locations, then get ready with a personalized training plan.

30 upcoming races

November 2026

Nov 7, 2026 TARC Stone Cat Trail Festival📍 Ipswich, MA6.2 mi · 13.1 mi · 26.2 mi · 50 mi

December 2026

Dec 5, 2026 TARC Winter Classic📍 Stoneham, MA8 mi · 32 mi · 40 mi

March 2027

Mar 27, 2027 estimated dateTails for the Trails 5k Canicross📍 West Newbury, MA3.1 mi

April 2027

Apr 3, 2027 estimated dateTortoise and the Hare Trail Races📍 Salisbury, MA3.1 mi · 6.2 mi
Apr 10, 2027 estimated dateMerrimack River 10 Mile Trail Race📍 Andover, MA10 mi
Apr 11, 2027 estimated dateF.O.R. 5K Trail Race📍 Wilbraham, MA3.1 mi
Apr 18, 2027 estimated dateTough Ruck Boston 26.2 For The Fallen📍 Concord, MA26.2 mi
Apr 24, 2027 estimated dateTARC Spring Classic📍 Weston, MA6.2 mi · 13.1 mi · 26.2 mi · 31.1 mi

May 2027

May 2, 2027 7 Sisters Trail Race📍 Amherst, MA12 mi
May 2, 2027 estimated dateCape Cod Trail Race📍 Falmouth, MA6.2 mi · 12.4 mi · 18.6 mi
May 8, 2027 estimated dateSpring for the Trails Half Marathon📍 Ipswich, MA13.1 mi
May 8, 2027 TARC Wapack and Back - Ashburnham, MA📍 Ashburnham, MA50 mi · 43 mi · 21.5 mi
May 8, 2027 Wapack and Back Trail Races📍 Ashburnham, MA50 mi · 43 mi · 21.5 mi
May 19, 2027 estimated dateThompson Island Outward Bound 4K Trail Run📍 Boston, MA2.5 mi
May 24, 2027 estimated datePowisset Farm Trail Run - Spring📍 Dover, MA1.5 mi · 3.1 mi · 5.6 mi · 8.3 mi
May 29, 2027 Chesterfield Gorge Ultra📍 Chesterfield, MA6.8 mi · 15.5 mi · 31.1 mi · 100 mi
May 29, 2027 estimated dateWildcat 5K Trail Run-Walk-Wag📍 Boxford, MA3.1 mi

June 2027

Jun 6, 2027 estimated dateThe Wine Run at Westport Rivers Vineyard & Winery📍 Westport, MA3 mi
Jun 12, 2027 estimated dateEdge Hill Trail Race📍 Ashfield, MA6.2 mi · 18.6 mi · 31.1 mi
Jun 12, 2027 estimated dateSchool's DONE! Raider Run 5K and Fun Run📍 Westhampton, MA1 mi · 3.1 mi

July 2027

Jul 9, 2027 Notchview Ultra📍 Windsor, MA100.7 mi · 6 h · 12 h · 24 h
Jul 10, 2027 estimated dateTARC Blue Hills Skyline Trail Run📍 Canton, MA7.5 mi

August 2027

Aug 21, 2027 estimated dateGreenbelt's Vineyard Hill Trail Run📍 Topsfield, MA6.2 mi · 3.1 mi
Aug 28, 2027 estimated dateAll of the Above Trail Fest - MA📍 Northfield, MA1.9 mi · 3.1 mi · 12.4 mi

October 2027

Oct 11, 2027 estimated dateCloudsplitter 100📍 Norton, MA97.9 mi · 68.8 mi · 31.1 mi · 15.5 mi
Oct 23, 2027 estimated dateSheriff's Meadow Foundation Trail Run📍 Edgartown, MA3.1 mi
Oct 24, 2027 estimated datePowisset Farm Trail Run - Fall📍 Dover, MA1.5 mi · 3.1 mi · 5.6 mi · 8.3 mi
Oct 24, 2027 estimated dateThe Baystate Dirty Dog Trail Run-Ruck-Walk 5k📍 Berkley, MA3.1 mi
Oct 24, 2027 estimated dateOx Trot 5K📍 Sturbridge, MA3.1 mi
Oct 31, 2027 The Next Loop Endurance Series - New England📍 Plainville, MA31.1 mi · 26.2 mi · 13.1 mi · 6.2 mi

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