Trail Run races in Boston, MA

Looking for trail races near you in Boston, MA? There are 21 upcoming trail races listed here. The next one is KINETIC RIDE on Sun, Aug 9, 2026 at 282 Merrimack St — see the full list below for dates, venues, and registration links, and browse trail races in other cities.

All 5K (220) 10K (22) Half Marathon (25) Marathon (6) Trail Run (21)

Sun, Aug 9, 2026 KINETIC RIDE 282 Merrimack St · Lawrence, MA · From $50 Trail Run Trail
Sat, Aug 15, 2026 Watermelon Wobbler 5k @ White Barn Farm White Barn Farm · Wrentham, MA · From $30 5KTrail Run Trail
Sun, Aug 16, 2026 Tour De Cure: New England 29 Hartwell Ave · Lexington, MA · From $260 Trail Run Trail
Sat, Aug 22, 2026 Greenbelt's Vineyard Hill Trail Run 656 Asbury St. · South Hamilton, MA · From $35 5K10KTrail Run Trail
Sun, Aug 30, 2026 UltraTrax Wachusett 41 Mile Hill Road · Westminster, MA · From $56 Trail Run Trail
Sun, Sep 27, 2026 Race for the Refuge Assabet River National Wildlife Refuge · Sudbury, MA · From $40 10KTrail Run Trail
Sat, Oct 3, 2026 Survival of the F.I.T.test - 34 Hour Trail Ultra 1464 diamond hill rd · Cumberland, RI · From $10 Trail Run Trail
Sat, Oct 3, 2026 2026 Shrewsbury Trails 5K 430 Lake St. · Shrewsbury, MA · From $12 5KTrail Run Trail
Sun, Oct 4, 2026 Houghton's Pond Trail Races (7 Miles and 3.7 Miles) Houghton's Pond Recreation Area, DCR Blue Hills Reservation · Milton, MA · From $30 Trail Run Trail
Sat, Oct 24, 2026 Womp Romp Wompatuck State Park - South Field · Norwell, MA Trail Run Trail
Sat, Oct 24, 2026 Pumpkin Pacer 5k @ White Barn Farm White Barn Farm · Wrentham, MA · From $30 5KTrail Run Trail
Sun, Oct 25, 2026 Powisset Farm Trail Run - Fall 37 Powisset Street · Dover, MA · From $20 5KTrail Run Trail
Sun, Oct 25, 2026 The Baystate Dirty Dog Trail Run-Ruck-Walk 5k Across from 41 Point St · Berkley, MA · From $5 5KTrail Run Trail
Sun, Oct 25, 2026 Run for the Hills 115 Prospect Hill Rd · Harvard, MA · From $15 5KTrail Run Trail
Sun, Nov 1, 2026 F.I.T. TrailFecta 2026 1464 Diamond Hill Rd · Cumberland, RI · From $15 5KTrail Run Trail
Sun, Nov 8, 2026 Upton 10.5K and Half Marathon Trail Race 205 Westboro Rd · Upton, MA · From $30 5KHalf MarathonTrail Run Trail
Sun, Nov 15, 2026 2026 GFRC Busa Bushwhack Trail Races 575 Pleasant Street (Route 30) · Framingham, MA · From $25 Trail Run Trail
Sun, Mar 14, 2027 F.I.T. 'Rock Trail Race 1464 Diamond Hill Rd · Cumberland, RI · From $15 5KTrail Run Trail
Sat, Mar 27, 2027 Tortoise and the Hare Trail Races 8 Lions Way · Salisbury, MA · From $25 5K10KTrail Run Trail
Sat, Apr 10, 2027 F.I.T. the Challenge OCR 4097 Diamond Hill Rd · Cumberland, RI · From $4 Trail Run Trail
Sat, Jun 5, 2027 F.I.T. 50k 1464 Diamond Hill Rd · Cumberland, RI · From $65 Trail Run Trail

New to the distance? Read trail vs. road racing, or set your target with the pace chart.

Quick answers

When is the next trail race in Boston?

The next Trail Run in Boston, MA is KINETIC RIDE on Sun, Aug 9, 2026 at 282 Merrimack St.

How many trail races are coming up near me in Boston?

There are currently 21 upcoming trail races listed in Boston, MA, each with a date, venue, and direct registration link.

What's the cheapest Trail Run in Boston?

The lowest listed entry right now is F.I.T. the Challenge OCR at from $4. Registration prices usually rise as race day nears, so early entry is cheapest.