I've done the D2R2 ride many times from Deerfield. We start from a large hay field. Across the field to the east is a towering ridge that spans from south to north as far as you can see. I've heard you can ride that ridge. The heatmap showed many have. That clinched it for me. With any luck, there might still be some fall foliage in the area.
To plan this route, I decided to give the Strava Route Builder a try. I found it has some minor quirks, but it has something nobody else has: heatmap overlay! You can use street, terrain or satellite views, with or without the heatmap overlaid. Street and path following can be turned on or off. I found this to be the most versatile off-road route planning tool yet. Previously, I'd have to go into Strava Explore and grab tracks from specific rides. I had no idea if they were a one-off or followed a popular route. With the heatmap, you know exactly where the popular routes area. Readers will be sad hear this may spell the end of Hill Junkie boondoggles. The heatmap takes speculation out of route building.
The plan was to park in Greenfield, take 10 miles of paved road south to Mt Toby, which I hit on my ride from Amhest last fall. There is nothing super special about Mt Toby, other than it is a superb 1000ft fireroad climb from the north. Descending the south is a different beast. It is four miles of ATV chunder buried under fresh leaf drop. Momentum is your friend on the sofa bike!
There was 0% chance of rain and nothing on the radar when I headed out, despite some pretty ominous looking clouds. I no more than pushed off when it started raining. WTF! It sprinkled the whole way to Mt Toby, enough to make the road and my feet wet. It was less than 50F. Fortunately that didn't last long and wasn't enough to make off-road terrain wet. I never saw another person on Mt Toby until I reached the bottom on the south side.
Crossing back over the Connecticut River, with most of the paved riding behind me, it was time to traverse the Pocumtuck Ridge. The Mt Sugarloaf State Reservation is at the southern terminus. It is a popular state park with a grand view from the summit. I have always wanted to ride up this paved climb, but not necessarily on a sofa bike with sub-20psi in the tires. The leaf peepers were certainly out. The view was worth one more paved diversion.
I would be great to follow the Pocumtuck Ridge Trail all the way back, but there are pesky interferences, like big cliffs along the way, that would not be fun to carry a bike up. So a bit more road brought me around to the north Mt Sugarloaf peak, which goes higher than the south prominence and is undeveloped. I discovered the route that loops up and around the rim is superbly designed singletrack. Some more great views of the valley below along the way.
Dropping back down Sugarloaf, in no time I was climbing up to the Deerfield ridge. This turned out to be doubletrack. With leaf drop nearing completion up top, you could see through the trees in many places to gauge climbing progress. A few openings afforded great vistas too, such as the field the D2R2 ride is run out of.
Dropping off the Deerfield ridge, there was some great singletrack. Crossing over a dirt road brought me past a pack of mountain bikers and onto freshly leaf-blown singletrack. Sweet! No more apprehension of sliding out on hidden roots and slickrock. I expected New England ridgeline gnar on this ride, but thus far, there was none.
It wasn't until I got into Rocky Mountain Park in Greenfield that I finally encountered gnarly ridge riding. More great vistas of Greenfield along the way, but the ridge was getting pretty short, only a few hundred feet above town.
I got back to the car with 41mi, nearly 5000ft of climbing in 4.1hrs. Even though there was a lot of paved riding in this loop, it didn't seem like it. Paved miles go by quickly, and way more than half of the time was spent off-road. I'll do this loop again, maybe with a few tweaks, but it was almost perfect right off the heatmap.
Sunderland Fire Tower at Mt Toby summit
Heading down the Mt Toby AVT track on south side of mountain
The south and north Sugarloaf outcroppings
South Sugarloaf from the bridge over the Connecticut River.
Observation deck in upper left.
Mt Toby on left from Mt Sugarloaf with the Connecticut River in between
South Deerfield from Sugarloaf observation deck
Overlook from the north Sugarloaf peak
Slightly different angle from above photo
Pocumtuck Ridge view of the fields the D2R2 ride start in
Greenfield from Poet's Seat