The first NW CT bootleg day trip was held on Sunday, August 31, 2025. The trip lauched at Pond Brook, down to Lake Lillinonah (the dammed Housatonic River), and up the Shepaug River to lunch at Roxbury Falls.
In attendance were Scott (@ScottS) in a dark green Wenonah Solo Plus, Keith (@themadindian) in a bright green Swift Shearwater and me in a carbon Swift Keewaydin 15. Here I am at the Pond Brook boat launch.
Scott and Keith starting out down Pond Brook on a very nice sunny day.
There is a blue heron on the left side of the stone wall below this rustic cabin.
Unfortunately, the shallower spots of the Shepaug are now infested with milfoil (or maybe hydrilla).
Although it does provide a surrounding vegetative look to parts of the trip.
Keith and Scott contemplating something as we approach Roxbury Falls.
Keith approaching Roxbury Falls from Scott's canoe.
Keith's approach from his canoe.
Landing for lunch on the huge exposed rocks at the falls, really a steep rapid, which has little water at this time of year.
Looking up the falls at what water there is.
Keith's landing spot at the falls.
Scott and my landing spot a few boulders away.
Scott looking down the falls from our lunch spot.
Scott and I trying to extricate ourselves from our tiny and boulder-strewn lunch spot lagoon.
Keith takes a picture of me . . .
. . . while I take a picture of him.
Keith then paddles downstream on the Shepaug.
We pass a nice private property on the way back on the Shepaug . . .
. . . which has a flock of geese.
In addition to the geese and herons, we also saw lots of ducks, a hawk and one or two bald eagles.
The 9.5 mile trip took about about 2:15 minutes to get to Roxbury falls, much of it into some stiff headwinds, and about 1:40 minutes to return mostly with a tail or cross wind, after about 40 minutes for lunch at the falls. There were no other landings or significant stoppages. So, it took about 4.5 to 4.75 hours total.
It was a pleasure meeting Scott and Keith for the first time, and I hope to meet some other CTN members on future impromptu trips I schedule.
In attendance were Scott (@ScottS) in a dark green Wenonah Solo Plus, Keith (@themadindian) in a bright green Swift Shearwater and me in a carbon Swift Keewaydin 15. Here I am at the Pond Brook boat launch.
Scott and Keith starting out down Pond Brook on a very nice sunny day.
There is a blue heron on the left side of the stone wall below this rustic cabin.
Unfortunately, the shallower spots of the Shepaug are now infested with milfoil (or maybe hydrilla).
Although it does provide a surrounding vegetative look to parts of the trip.
Keith and Scott contemplating something as we approach Roxbury Falls.
Keith approaching Roxbury Falls from Scott's canoe.
Keith's approach from his canoe.
Landing for lunch on the huge exposed rocks at the falls, really a steep rapid, which has little water at this time of year.
Looking up the falls at what water there is.
Keith's landing spot at the falls.
Scott and my landing spot a few boulders away.
Scott looking down the falls from our lunch spot.
Scott and I trying to extricate ourselves from our tiny and boulder-strewn lunch spot lagoon.
Keith takes a picture of me . . .
. . . while I take a picture of him.
Keith then paddles downstream on the Shepaug.
We pass a nice private property on the way back on the Shepaug . . .
. . . which has a flock of geese.
In addition to the geese and herons, we also saw lots of ducks, a hawk and one or two bald eagles.
The 9.5 mile trip took about about 2:15 minutes to get to Roxbury falls, much of it into some stiff headwinds, and about 1:40 minutes to return mostly with a tail or cross wind, after about 40 minutes for lunch at the falls. There were no other landings or significant stoppages. So, it took about 4.5 to 4.75 hours total.
It was a pleasure meeting Scott and Keith for the first time, and I hope to meet some other CTN members on future impromptu trips I schedule.
