Riding off road, by accident

My brother and I were out in western Massachusetts, in Williamstown, after we met at my sister's house in New York for a family gathering.  Both of us thought we might as well bring our bikes along with us.  I was coming from the Cape and my brother was coming from Virginia.  This was in May 1997.  I had my only bike, a 1984 Trek 520.  My brother had his 1995 Trek 520.  His was the 520 that we think of now, a dedicated touring bike, bought at my suggestion for a tour in northern New Hampshire a couple of years before this.  My 520 was more of a  randonneuring bike, although not by the 650b, short trail standards of today's resurrected constructeurs movement.  The 620 was full touring bike of the time, with more eyelets for fenders and a lower rider front rack.  And I was in a state when I thought I needed narrow tires to go fast so I had narrow tires on it in 1997, even though I was still taking it out for an occasional tour.  So this is what we did:

We parked in Williamstown, which is a nice college and prep school town that we both were familiar with from visiting when my sister taught there a couple of decades before then.  I had a map, a state highway map, and we followed it. We took MA 43 south out of town and suddenly I saw this turn, off to Hopper Road, which sort of looked park-like, so we took it.  I wanted to head south and after a short run east, the road did turn south (which I determined by checking out the sun and my watch).  Great.  We followed the road for a while and eventually it stopped.  I was a bit younger then, not yet 40, and I had energy, enthusiasm, and a brother who would go along with me, if he thought that I thought that I was right.  And I was wrong but thought I was right.  The road turned to dirt and then it turned to a trail.  Then it turned to a steep trail.  Then the mosquitoes came out.  Actually they had been out an about but now we weren't going very fast and the woods were really damp from recent rains and we were prime targets for their lunch.   And then the trail got steeper and our tires weren't all that useful for the surface we were trying to ride on (my brother also seemed to think that thinner tires were faster and he had a touring bike which wasn't all that fast to begin with).  But the sun seemed to indicate that we were heading in the right direction so we followed the trail despite the mosquitos and the trail conditions.  I'd like to say road conditions but there was nothing that would make me think that the trail was ever a road or would ever be one.  Eventually we eventually started going downhill and we persevered and found Route 7, which I knew we would.  Or thought we would.  It was a small detour, maybe a mile or so but an adventurous one that took 20 minutes or so.  And one that my brother didn't let me soon forget.

The route, as I remember it.  Use caution and don't assume that the landowners don't mind you  traversing their land.  I did a similar route with my wife in 2003 but we skipped the off road riding.

This is what a 1984 Trek looks like (I have nothing to do with this Flickr page).  But mine was never quite so nice as this one (plastic fenders, blackburn front [low riders] and back, and it never saw a leather seat):

I last toured on my 1984 Trek 520 in 2001.  I lent it to various friends and took it back into my possession in 2004 after the last borrower left town.   I donated the old 520 to Bikes Not Bombs in 2005.  It had about 6000 touring miles on it in addition to a lot of other miles.  If I had it today, I would be 27x1.5 inch tires on it, if they would fit.