Biking in the Deerfield Valley
I consider myself a casual bike rider. Usually, riding for exercise and to enjoy the scenery. My bike riding began when I was about six years old after my father invested $15.00 for a used one-speed bike for me and one for my younger sister. All summer long, we rode them up and down our driveway. Since then, I’ve owned many bikes and logged thousands of miles.
Currently, I have a Trek Cross-Rip- which is somewhat of a hybrid bike. While built like a road bike, it is suitable for dirt road riding and for me, a bit more stable than a road bike. And if we are being honest, it gives me a reason or excuse not to ride the single-track trails. I am not as brave as I once was.
Southern Vermont has many wonderful places for bike riding. See the Play tab on this site for local woods biking options. Many of these trails are very popular with hikers as well so you will need to be alert. Plan ahead, though, as not all trails are designated biking trails.
There are many rides in the area I enjoy. Most will include some dirt road riding. These roads are generally smooth and well traveled during the summer riding months. I have given the approximate distances as a rough guide to be used in planning. The time for each ride will depend upon the rider(s), the number of stops, etc. Also, they are listed as loops so you can begin where it makes sense for you.
Unfortunately, paved roads in this area do not provide much in the way of a shoulder. They are certainly rideable, but for me, not much fun.
During the summer of 2022, biking on any part of Route 9 between the Marlboro town line and Brattleboro, is not recommended due to the road construction.
Looking for more gentle rides?
Lake Raponda Road in Wilmington: This is a nice flat dirt road for a family ride. This is about two miles one way. You could end up at the town beach for a quick cool-off after your ride.
Handle Road: Handle Road in Wilmington and Dover can be ridden as an out and back. This road is paved in its entirety and provides a few hills. This is approximately 6 miles one way.
Blue Brook Road (Alternate Route 100) is about three miles long. The road follows the brook, and is mostly dirt and shaded. It is a gradual uphill as you head north. You could turn around and make this an out-and-back ride.
OR if you want to add some miles and a few hills: At the end of Blue Brook, turn left on route 100 and head south. There is a wide shoulder so you can ride well off the road. Turn into the North entrance of Mount Snow and continue to ride through the parking lot and end up on Handle Road near Snow Lake. Continue south on Handle Road. Take a left at Tannery Road and end up back on 100.
Still want to add more miles: Continue south on Handle Road which turns to Coldbrook Road at the Wilmington town line. Continue to Route 100 then head north to complete the loop.
Looking for some hills?
Higley Hill Road loop. Head east on Higley Hill Road (from the junction of route 100 and Higley Hill road in Wilmington) until you get to Upper Dover Road. This is a gradual uphill ride. Head north (left) on this dirt road. There are rolling hills and beautiful views of the valley to the east including Mount Monadnock. Where the road ends, turn left onto Yeaw road (also dirt.) This will take you to Dover Hill Road. This is about three miles of paved downhill where it rejoins Route 100 in Dover. Head south to return to Higley Hill Road. This is about 12 miles.
(Caution- this does require crossing Route 9 in Marlboro)
Shearer Hill Loop. This loop starts at the junction of Shearer Hill and Route 9. Head south on Shearer Hill and head up! At the top of the paved climb and just past the quarry, bear left. The road turns to dirt here. Take the next left turn onto Grant road. When it comes to the end, turn left onto Butterfield Road. Continue until you come to route 9. Cross carefully to Hughes road. Take a left turn onto Higley Hill road. This will be dirt for a few miles- Continue on this road until you get to Lake Raponda road and turn left. To complete the loop, turn west (right) on Route 9 and return to Shearer Hill Road. This makes a nice hilly approximately 12-mile route.
Equipe Sports in Dover has a wide variety of bikes for rent and for sale available. Need a tune-up? Give them a call.
Wherever you decide to ride, be mindful of traffic. Please ride single file with traffic. Use arm signals when turning or stopping. Here is a link to the Vermont bicycle statutes.
Enjoy the many bike rides the area has to offer!
Written by Bridget Cole. Bridget grew up in Wilmington. After spending a few decades in New York and Colorado, she is currently back in Southern Vermont. She is a former dairy farmer and current educator. She enjoys hiking and biking and being outdoors.