Well, it happened. New England finally cooled down. With temperatures in the upper-70s and the dew point in recession, summer is finally starting to feel like summer has historically felt. And given the heat and humidity we’ve endured to get here, the vibe in Boston lately has been like the liberation of France. Last night, I went for a run around Jamaica Pond and found that I still had enough gas in the tank to sprint over to Arnold Arboretum just in time to catch the pink glow of a sunset from the Willow Path. This morning, I walked from my house to the Seaport, fueled by two rosemary bagels. It felt amazing to take a long walk outdoors again. And so, with the near future looking temperate, I want to tell you about one of the greatest long walks in New England.
I first learned about the Berkshire County High Road while visiting my friend Mike McGinn in the hilltowns of Western Mass. (As top brass of America Walks, Mike is uniquely tapped into the foot travel beat.) The concept is tantalizingly yet simple: Imagine a trail running along the spine of the Berkshires, from Williamstown to Great Barrington. Now imagine if that trail were to go through Pittsfield, Lenox, Adams, and other towns nestled within the mountains. Finally, picture a trail that visits high peaks, bogs, and dreamy woodlands, while remaining relatively gentle and never reaching White Mountain grade steepness. That’s what the High Road is: a town-to-countryside long trail that’s designed not to brutalize, but to enchant. And with the trail winding through villages, opportunities to connect to transit, restaurants, and hotels are vast.