“We shall not cease from exploration, and the end of all our exploring
will be to arrive where we started
and know the place for the first time.”
— T.S. Eliot, Little Gidding
One reason I set out on this walk was to revisit the places that helped shape my life. Back on Franconia Ridge I first caught the passion for the outdoors and then on Monadnock, watching its broad sweep of six New England states on a clear day, I felt the spark of wanting more views on New England’s craggy peaks.
But how would I see southern New England now, after over two decades out West, with its rolling hills, old wooded roads, and gentle grades, as I walked toward the ocean?
It turns out I did find, if not wilderness, then at least wildness, as I followed the trails south from Monadnock.
After seeing my brother I made my way to the Wapack Trail just north of the Massachusetts border.
The terrain still offered a few climbs, including Watic Peak, but the grades began to ease as I crossed the state line
I had one somewhat significant climb to Wachusetts Mountain.
Anyone who grew up within the orbit of Boston or Providence probably just hummed the jingle.
I had one more decent climb up Wachusett Mountain—
and anyone who grew up within the orbit of Boston or Providence probably just hummed the old jingle.
For many, Wachusett is the first mountain they ever ski. Though I’d never been there until this walk, it was part of the backdrop of my winters growing up—thanks to that jingle and the friends who planned their weekends around it. (My brothers and I mostly sledded until about age 11 or 12, when we got handed a shovel and told to clear the driveway—and the older neighbors’ too.)
A busy weekend on the trails, but during my morning hiking a long-time reader recognized me, and we hiked together for a few hours. I appreciated his local knowledge and good company.
⠀
From there, the trail dropped below 1,000 feet… then 500 feet… into a land of rolling hills, old farm lanes, and deep history.
I passed a 1750s tavern where Gen. Lafayette once reviewed troops across the street, and just around the corner stood a “new” 1840s schoolhouse.
The Mid-State Trail isn’t wilderness, but it’s rich in history and full of character. The fall colors were more vivid here than the muted tones up north—scarlet and gold scattered across old stone walls and quiet woods.
All told, an enjoyable stretch even where the corridor felt built up.
I even had a small miracle on one cold, rainy morning—a farm stand right on the trail was open at 7:30 a.m., serving hot coffee and bagel sandwiches. A dry spot, a warm drink, and good timing can feel like trail magic when you least expect it.
I eventually crossed into my home state of Rhode Island.
The North-South Trail leads from here to the Atlantic… and to the end of this journey.
