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United States·2026

Pittsfield, MA

Pittsfield anchors the Berkshire cycling scene in western Massachusetts, with rolling terrain and mountain passes that define races like the Berkshire 40 and the Bike Hub Southern Discomfort. Runners have access to wooded trails through the surrounding state forests—the Tails & Trails State Forest Run covers 50km through this network—while the elevation swings between 200m in town and 700m+ in the hills nearby. The region's proximity to the Taconic Range and Green Mountains makes it a serious training ground for gravel and mountain cyclists.

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