I read on-line about a group of BMW riders who had come up with
"The Puppy Dog Route," which is a series of mostly dirt roads that one can take from the southern border in Massachusetts to the northern border in Newport, VT and Quebec. The link has the GPS files for download. I took a day off from work and rode the southern part of the Route. I made it from Brattleboro to S. Woodstock, nearly 100 miles.
The Route is located entirely on town roads with pretty good maintenance. Most of the roads are actually residential areas, only a few are completely in the wilderness, but you are riding in and out of the woods most of the time. There were a few roads that are not maintained in the winter. They are a little rougher, but still very do-able for a big bike. Most of the roads are one and a half lanes wide. Some of these dirt roads were as hard as asphalt and as wide as a state highway though. You could easily do 40 mph on them. These tend to be the "major" roads in and out of some of the remote towns in Vermont. Probably the biggest hazard are the cars. People tend to drive fast and there can be blind corners and uphills.
The Route is great for big-bikes, but you could do this ride with a street bike with decent tires. In fact there is a lot of pavement on this ride. I would say it's about 60/40 dirt/pavement. The paved roads are nice though. You won't see much traffic. I don't recall seeing a single traffic light.
These are typical of the road conditions you'll find:


Some of the roads have recently been maintained:

At the Townsend Dam

There are several lakes along the route:

Some great vistas, I believe this one is in Windham. I think that is Mount Monadnock in New Hampshire in the distant background.


Some of the roads run along rivers:

The PDR has everything from tight first gear turns to WOT:


In South Reading there is a bridge out.

Lunch:

I did some sightseeing on the ride home, getting home without much interstate travel. This is the Round School House in Brookline. Very interesting history behind it:



I talked to one of the ladies from the town's historical committee. She was telling me that school just finished a complete renovation. The brickwork, floors, rear retaining wall and roof were refurbished. She said because the roof is round each of the shingles had to be hand cut to fit. They are hosting a wedding tomorrow and should have an open house in October to coincide with the foliage season.
From there I went up Putney Mountain Road which has some excellent dirt riding and views, over 1700 feet in elevation.

I love Vermont for the "time machine" factor. I wonder how long these vintage street signs have been doing their job?

The speed limit sign is metal with raised lettering:

A couple of observations about the southern leg of the PDR:
-although this wouldn't be a good route for enduro bikes there are a lot of dirt roads and trails off the route that would probably be more interesting.
- whoever constructed the route did a good job with the mixture of roads, scenery and availability of food and gas.
- there were two road closures on the original GPS file: Blue Hill Road in Chester is no longer a through road. There's an easy ride-around on Route 11. Also the bridge is under construction in South Redding, near Keepers Cafe. The Cafe appeared to be closed too. I made corrections to the original gpx file but the revised file is too large to attach here. Send me a PM or email and I’ll email it to you.
The Puppy Dog Route would be perfect for a weekend of dual sporting. The halfway point is a great spot for a stop-over and you could ride the northern half the next day.
I've also been working this summer on a Massachusetts companion to the PDR. I call it the "Trans-Mass Trail." It allows you to ride from the Connecticut border in Winsted all through Western Massachusetts and then link up to the PDR in Greenfield, Mass. It's only about 90 miles and is probably about 65-70% dirt. You can get more information on it
here.