You’d be hard pressed to find a place with as many diverse trails and scenic, rugged landscapes as Western Massachusetts. As the more rural part of the state, Western Mass features a huge variety of gravel roads, dirt paths, light trails, and even more aggressive mountainous terrain to explore.
With all these exciting and beautiful trails, you likely won’t be surprised that the Western Mass region is a popular trail running hub. Western Mass trail races will have you scrambling over rocks, tackling steep climbs, and pushing yourself to your limits. But if you’re a beginner interested in trail running, it can be overwhelming to know where to start.
At Marathon Sports, we know running inside and out – and that doesn’t just mean road running. We also have a huge range of trail running shoes and hiking boots designed to give you the grip and traction you need to fly up and down hills. And with this focus on trail shoes, we also get to know all the local paths and trail races so we can provide you with the best shoes, gear, and advice for your needs.
In this guide to the best trail races in Western Massachusetts, we’ll highlight some of the toughest and most exciting races where you can take on all the challenging, rugged terrain the region has to offer. Keep reading to find the perfect next trail race to add to your calendar.
Best Western Mass Trail Races
Whether you’re a Western Mass local or are looking to travel to a trail-heavy area for your next race, Western Mass trail races have so much to offer every runner or hiker. Here’s your guide to five of the best options and who should consider trying out each race.
Seven Sisters Trail Race – Most Challenging Trail Race
Looking for a true trail running challenge? Want to run among some of the most impressive and elite trail runners around? Look no further than the Seven Sisters Trail Race.
Taking place in May, this technical 12-mile out-and-back race isn’t for the faint of heart. The course carries you through seven peaks in Holyoke Range State Park, starting in Amherst, MA. The course is a technical, single track trail along the Metacomet-Monadnock trail with around 3,500 total feet of elevation gain.
With such a rugged, technical course, Seven Sisters has certainly earned its reputation as one of the most challenging trail races in the Northeast. But if you’re up for the challenge, the scramble across the steep and rocky trail is absolutely worth the epic views and incredible sense of accomplishment this race has to offer.
Mt. Toby Ultra and Trail Races – Best Trail Ultra
Runners who want to put their trail running to the test with a trail ultra should check out the Mt. Toby Ultra and Trail Races. This stunning early season 50K – typically taking place in April – offers a low-key atmosphere paired with incredible views along Mt. Toby.
Located in Sunderland, MA, Mt. Toby trail races feature rugged double and single track trails that loop you through some of the mountain’s most beautiful sights and hidden gems. As you tackle the 50K’s 6,100 total feet of elevation gain, you can take in scenic water views, run alongside a waterfall, and even traverse a rock cave.
And the good news? You don’t have to sit this one out if you’re not ready to take on a full 50K. There’s also a 24K and 13K race that allow you to push yourself on the trails while taking in Mt. Toby’s beautiful scenery.
Mt. Tom Trail Race – Most Breathtaking Trail Views
If you want to blend challenging trail running with Fall New England leaf peeping, the Mt. Tom Trail Race is for you.
The Mt. Tom Trail Race takes place in October, so you can tackle the tough, technical Holyoke course while enjoying breathtaking views during peak foliage season. The course weaves through Mt. Tom State Park, starting and finishing at Lake Bray and taking you through rugged and challenging single track terrain.
The Mt. Tom Trail Race offers a huge range of distance options, so runners of all skill and experience levels can take part in the fun. There’s a solo and relay 25K, which has around 3,300 feet of climbing. There’s a 10K with 1,400 feet of climbing, and even a 5K fun run/hike with 600 feet of climbing.
But no matter which event you choose to do, you’re guaranteed exceptional fall views and a fun and challenging race day experience.
Chesterfield Gorge Ultra & 25K – Best Non-Technical Trail Race
Many New England trail races will leave you scrambling over tough, technical terrain. But if you’re looking to challenge yourself in a different way on a less technical course, you should consider the Chesterfield Gorge Ultra and 25K.
This race boasts miles and miles of stunning rolling hills along a rocky but non-technical jeep trail. However, while the course itself is more accessible than some other trail races on this list, the Chesterfield Gorge Ultra and 25K is by no means an easy race.
As the only 100 mile race in Western Mass, the Chesterfield Gorge Ultra is the perfect opportunity to push your running limits in a picturesque gorge along the Westfield River. Along with the 100 mile, you can also challenge yourself with an 11K, 33K, 50K, or 50 mile option. Every 10 mile out-and-back has around 750 feet of elevation.
The race typically takes place in late May/early June, so you should prepare yourself for warm or unpredictable weather conditions. But with lots of support, food, and hydration along the way, Chesterfield Gorge offers an exceptional atmosphere along a tricky but non-technical course.
Wild Thing 5K/10K – Best for Beginner Trail Runners
Who wouldn’t want to go for a run through the Berkshire’s wild and rugged forest? The Wild Thing 5K and 10K in Lenox, MA opens up this opportunity to both experienced and beginner trail runners, offering an accessible course through Pleasant Valley Wildlife Sanctuary.
You can choose between a 5K and 10K race option, both of which take you through forest trails and rolling carriage roads with uneven trail terrain. And after you cross the finish line, you can celebrate your accomplishments with post-race food and music at the big red barn. There’s even a nature-inspired costume contest with a prize for best dressed.
No trail races are easy – but if you want a more approachable race with a 5K and 10K option, the Wild Things trail race is a fantastic introduction to trail running and hiking in Western Mass.
The Best Trail Race in Western Mass: Final Thoughts
For years, trail runners from New England and beyond have flocked to Western Mass to take on some of the toughest trail races around. All five of these trail races require grit, resilience, and a sense of adventure. And if you’re looking for an off-road challenge for your next race, you can’t go wrong with any of these Western Mass trail races.
From long, challenging treks on technical terrain to fun 5Ks on more groomed trails, the scenic Western Mass trails have something for everyone. And at Marathon Sports, we’re here to help you prepare and make sure you have everything you need for your next outdoor adventure. Stop by your local store to find the right trail shoes for you, stock up on nutrition and hydration needs, or just to talk trail running and ask any questions you may have.
Our footwear experts are here for all your road and trail running needs. So whether you’re just getting started or have plenty of experience battling the toughest New England trails, we’re excited to connect and be a part of your next trail adventure.
