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Welcome to the Berkshire Highlands!. From skiing to rafting, zip lines to bike trails, the Berkshire Highlands is the adventure capital of New England. This website is our way of getting the word out about the great events we host here in the Highlands. You'll find races, music, food and other great outdoor happenings that capture the essence of this unique area. 

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Check back in periodically to see what new events are happening around the Berkshire Highlands and thanks for being an active part of the Berkshire Highlands community!

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Check out the Berkshire Highlands Pentathlon

Berkshire Highlands Pentathlon

April 4, 2020

The annual Berkshire Highlands Pentathlon features many of the best outdoor adventures in our area, and can be done solo or as a team.  The five events - a 4.2 mile road/trail run, a 16 mile cycling leg, 2 mile kayak, a 2 mile adventure run, a mile hike to the top of the mountain and a downhill ski to the finish - can only happen on the same day at the turn of the seasons.  It may be a bit cold for road biking and kayaking and a bit warm for skiing, but where else can you do it all on the same day?

Learn more