On Saturday, March 29, 2025, the Berkshire Highlands Pentathlon returns to Berkshire East Mountain Resort in Charlemont, Massachusetts, promising an exhilarating day of outdoor adventure and community spirit. This event is a unique opportunity to experience some of the best outdoor pursuits in the region, all in one day, early in the spring.
The Event
The pentathlon consists of five challenging yet rewarding legs:
4.3 Mile Run
Starting on pavement through Charlemont, the run transitions into a mix of woods roads and trails around the Warfield House before descending to the Run-Bike transition at Zoar Outdoor.
18 Mile Bike Ride
A rolling out-and-back course on Route 2 and Zoar Road, culminating at the Mohawk Park Campground.
Paddle Leg
A short run to the river followed by a nearly two-mile paddle upstream and back, with a mix of class 1 and potential class 2 rapids.
1.75 Mile Adventure Run
Featuring obstacles and varied terrain, this run leads participants back to Berkshire East.
Climb and Ski
Athletes ascend the Competition ski trail and descend through gates to the finish.
Registration and Team Opportunities
There's still time to assemble a team or participate solo in the pentathlon. Registration is open for various categories, including:
- Bravehearts (individual participants)
- Family teams
- Teams of three to five members
Discounts are available for family teams and entrants under 19 years old. You can register online at BikeReg.com or on the day of the event.
Volunteer Opportunities
What makes the Berkshire Highlands Pentathlon truly special is the dedicated crew of volunteers who support the event each year. If you're interested in contributing to this memorable community event, consider volunteering!
Volunteer Perks:
- Floodwater Brewing pint fill-up
- Lunch
- Tech shirt
- Coupon to Cold River Package Store
Your support is invaluable, and the race couldn't happen without you.
A Fun Day for All
The pentathlon promises to be a fun-filled day with great food, beer, and raffle prizes. Whether you're racing or volunteering, it's an excellent opportunity to connect with the community and enjoy the beautiful Berkshire landscape.
Sign Up Today!
Registration: Berkshire Highlands Pentathlon 2025 Registration Form
Volunteer Sign-Up: 2025 Volunteer Sign-Up Form
Join us on March 29, 2025, for an unforgettable day of adventure and community spirit at Berkshire East Mountain Resort!

Photo credit: Berkshire Highlands Pentathlon, Berkshire East Mountain Resort, and Art Schwenger
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