Bridgewater Loop

 May 11, 2024

The Money Shot

It was high time that I take the new Synapse into the Berkshire Foothills. No one was available to ride to OOF Saturday morning except Mike so rather than have him drive all the way down to Sandy Hook I suggested that we meet in Bridgewater and ride north and get some breakfast in New Preston.

We bombed down the Rt 67 and rode along the Shepaug River in Roxbury. 

Then we hit my favorite hill climb in Roxbury, Painter Hill.

The climb before the cow field hits 12% and the roller to the Oak Tree maxes out 15%

The Synapse felt wonderful climbing

and the cows, probably being weened from their mothers.

It was a blue bird day at Topland Farms today

The view from Painter Ridge was spectacular!

This is the payoff for that climb

Spring was in full bloom, the Dogwoods were blooming and new Chip Seal was on the road.

Turning onto Nettleton Hollow, we continued north into Romford, passed Rumsey Hall and started climbing Whittlesey Road. A nice dirt road that's easy for road bikes.

Nearly a mile long and in the middle of the steepest part is what I call the Money Shot.

It's this incredible view down this small vale between two farms back towards the Shepaug River that I love to see every time I ride through and it makes climbing this steep ramp worth every pedal stroke.

We stopped at the Smith Cafe in New Preston for a late breakfast.

I had the Classic and it was delish!

Paralleling Rt 202, we rode through Marbledale

and then we started climbing dirt again on Crossmon and Old Northville Roads. 

It turns to pavement before Buckingham Road, and then it's paved all the way to the top

with some punchy little ramps till you get to the top of Old Ridge Road.

The reward is an eastern view of the Housatonic River Valley and beyond into eastern New York.