The Berkshire Highlands Pentathlon returns to Berkshire East Mountain Resort on Saturday, March 28, 2026, inviting runners, riders, paddlers, and skiers—as well as volunteers—to spend a full day playing outside for a good [...]

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 [...]

Gather your team and register today for the Berkshire Highlands Pentathlon! This annual event, hosted by Berkshire East, is unique in that it is only possible in New England’s early springtime when you can run, bike, kayak, and ski all in the same day. Mark your calendar for [...]

Registration for the Berkshire Highlands Pentathlon is open which means it’s time to gather your team together. This annual event hosted by Berkshire East is really unique in that it is only possible in New England’s early springtime when you can run, bike, kayak, and ski all in the same [...]

Early April is an amazing time of year in Franklin County, Massachusetts, when Winter and Spring overlap. You can ski in the mountains in the morning and bike or kayak in the afternoon. With the combination of these Winter and Spring conditions, it is the perfect time of year to hold the Berkshire Highlands Pentathlon, an annual event which [...]

This is an amazing time of year where Winter and Summer overlap in our area. You can be skiing in the mountains in the morning and biking on the roads or kayaking the rivers in the afternoon. This makes it the perfect time of year to hold a pentathlon, combining five outdoor activities into one event. The 8th Annual Berkshire Highlands Pentathlon is this Saturday, April 6, starting and finishing at Berkshire East Mountain Resort.

The race has five legs- a 4 mile trail run, 16 mile road bike, 2 mile river paddle, 2 mile obstacle course run, and finally a climb up Berkshire East to a ski/snowboard down to the finish line. Participate in the pentathlon on your own as a “Braveheart” or as part of a team of two or five people. There is a special category for family teams, as well! The pentathlon is a fun way to challenge yourself in a variety of sports in the same race. After the race, all participants are welcome to a free meal at Berkshire East and a free beer from Berkshire Brewing Company!

You can also be part of the fun as a volunteer! The Berkshire Highlands Pentathlon is still seeking volunteers to help time and monitor the course. Volunteers are crucial to making this event happen and receive a free T-shirt and meal to say thanks for their help. Sign up for a volunteer role here.

Of course, supporters are always needed to boost up the participants. Come out and cheer on the participants as they challenge themselves. There are several great viewing areas for different legs of the course. Check out the best places to spectate here. Participants will meet at 10:15 am and the race starts at 11:00 am.

For more information and to register for the Pentathlon, click here.

Good luck to all the racers!