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A couple of weeks ago a friend and I took an overnight from Cape Cod up to Woodstock, mostly on back roads. It was just before their foliage season, so the roads were clear of leaf peepers and the rate at the hotel was reasonable.
250mi each way; only negative was on the way up we ran into some mist/drizzle.
Another nice back road ride is out to Stockbridge area. Even Rt9 is nice out there...we did an overnight in Pittsfield, but there are plenty of towns and back roads.
Sure.....we wanted to get out of the Boston metro area quickly, so we took: I-495 N to MA-117 W up to MA-2 W to MA-140 N in Westminster.
Follow MA-140 N to NH 9W in Keene
Follow 9W to VT100 N in Wilmington, VT
Follow VT 100 N to Woodstock
We used Google Maps to plot the route at home, then sent the specific directions to our phones, so when we stop we can check for the next turn, etc.
GL .... its a really nice ride.
A couple of months back, I did a similar day trip. Took 495 to 2 East to 63 N to 119 N to Rt 30 and picked up Rt 100. Rode to Newport VT and boogied back home via the interstates. Weather was great. I did feel that Rt 100 was a little beat up, but given that its a secondary road and the weather for the region, its somewhat expected. I love VT!
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