Massachusetts · Trail
Trail Races in Massachusetts
Massachusetts currently has 5 upcoming trail races with a confirmed date listed in RaceRove. They take place in Cranberry Isles, Framingham, Hamilton and Salisbury and elsewhere.
Among them, 2 offer a 5K, 2 a 10K and 1 a half marathon. An event with several distances counts once for each.
Another 6 annual trail races are waiting for next year's date to be announced.
This page is the same for everyone, so it can't know where you are. Open the race search from here, which starts with Massachusetts's trail races, and set its Near filter to your city to keep only the ones around you.
- Upcoming, date confirmed
- 5
- Active listings
- 11
- Cities with trail races
- 11
Upcoming trail races in Massachusetts
All 5 with a confirmed date, soonest first.
Dates come from each race's own listing. Always confirm on the organiser's site before you book travel.
Largest trail races in Massachusetts
By estimated field size across all distances at the event.
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Houghton's Pond Trail Races (7 Miles and 3.7 Miles)Milton, MA Usually held in October · next date not announced7 Miles3.7 Miles ~300 runners
Trail ultramarathons in Massachusetts
Trail races with a distance of 50K or more, a fixed-time format, or billed as an ultra (the race search's Ultra filter): confirmed dates first, soonest first.
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Free to Run Trail RacesPittsfield, MA Usually held in September · next date not announced50K25K10 Miler5 Miler
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WWII Veterans Memorial Trail Weighted RaceMansfield, MA Usually held in October · next date not announced6hrs
When trail races happen in Massachusetts
- January
- 1 upcoming trail race
- March
- 1 upcoming trail race
- July
- 1 upcoming trail race
- November
- 2 upcoming trail races
Massachusetts cities with the most trail races
- Cranberry Isles
- 1 upcoming trail race
- Framingham
- 1 upcoming trail race
- Hamilton
- 1 upcoming trail race
- Salisbury
- 1 upcoming trail race
- Upton
- 1 upcoming trail race
Annual trail races awaiting their next date
These trail races are held every year, but the next date isn't in the listing yet. The month shown is when each is usually held.
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Houghton's Pond Trail Races (7 Miles and 3.7 Miles)Milton, MA Usually held in October · next date not announced7 Miles3.7 Miles ~300 runners
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Free to Run Trail RacesPittsfield, MA Usually held in September · next date not announced50K25K10 Miler5 Miler
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Greenbelt's Vineyard Hill Trail RunSouth Hamilton, MA Usually held in August · next date not announced5K10K
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Powisset Farm Trail Run - FallDover, MA Usually held in October · next date not announced8.3 Miles5.6 Miles5K1.5 Miles
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The Baystate Dirty Dog Trail Run-Ruck-Walk 5kBerkley, MA Usually held in October · next date not announced5K
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WWII Veterans Memorial Trail Weighted RaceMansfield, MA Usually held in October · next date not announced6hrs
More ways to browse Massachusetts
Trail races in nearby states
How RaceRove picks trail races
A race is on these pages when its name, its list of distances or its listing's notes say "trail". That is the rule the Trail filter in RaceRove's race search uses, so a race is a trail race on both or on neither. A race on dirt roads or mountain paths that doesn't call itself a trail race isn't counted, and neither is one whose only mention of a trail is in its description.
Trail races come in every length, from a few miles in a city park to 100 miles in the mountains. Off the road, the same distance usually takes longer: read each race's course description for its climbing, its footing and any cut-off times before you register, and plan your pace from those rather than from a road time.
Mud runs and obstacle races aren't a category of their own in RaceRove; one is on these pages only when its listing says trail. To get ready for one, the obstacle course race training guide covers Spartan, Tough Mudder and mud-run preparation. Thinking about a first ultramarathon? The ultramarathon and trail training plans run from 50K to 100 miles, and the Ultra Classics list gathers the best-known ultras.
Guides from the RaceRove blog
- 9 min read Obstacle Course Race Training: How to Prepare for Spartan Race, Tough Mudder and Mud Runs How OCR training differs from a running plan: building grip strength, upper-body pulling power and running fitness for Spartan Race, Tough Mudder and local mud runs.
- 9 min read Ultramarathon and Trail Training Plans: 50K to 100 Miles How ultra training differs from marathon training, phase-by-phase 50K and 100-mile plans, gear and fueling basics, and how to pick your first ultramarathon.
- Blog All guides Planning advice for finding, choosing and travelling to races.
Trail Races in Massachusetts: common questions
- How many trail races are there in Massachusetts?
- RaceRove currently lists 5 upcoming trail races in Massachusetts with a confirmed date, plus 6 annual trail races whose next date hasn't been announced yet.
- What counts as a trail race on RaceRove?
- A race whose name, list of distances or listing notes say "trail": the same rule as the Trail filter in RaceRove's race search, so a race is a trail race on both or on neither. A race whose only mention of a trail is in its description isn't counted, and neither is one on dirt roads or mountain paths that doesn't call itself a trail race.
- Which Massachusetts cities have the most trail races?
- By upcoming trail races listed in RaceRove: Cranberry Isles (1), Framingham (1), Hamilton (1), Salisbury (1) and Upton (1).
- What is the biggest trail race in Massachusetts?
- By estimated field size, the largest trail race listed in Massachusetts is the Houghton's Pond Trail Races (7 Miles and 3.7 Miles), with about 300 runners across all of its distances.
- Are there trail ultramarathons in Massachusetts?
- RaceRove lists 2 annual trail races in Massachusetts with a distance of 50K or more, a fixed-time format, or billed as an ultra (the race search's Ultra filter), none with a confirmed date yet.
- How do I find trail runs near me in Massachusetts?
- Open the race search from this page: it starts with Massachusetts's trail races. Set its Near filter to your city and how far you'll travel, and only the ones around you are left. This page can't see where you are.
Search every trail race in Massachusetts
The race search with this state and its Trail filter on: set Near to your city and a radius, then narrow by month, distance and field size.