My usual Sunday morning bike ride into Dover and Sherborn becomes even more enticing in fall. You can begin this jaunt in Newton, Needham, Wellesley, or South Natick, but it’s the core loop around the rolling hillsides of Dover and Sherborn that will grab your attention.
Start on Centre Street past the Dover town green and you will soon be pedaling uphill and sweeping downhill along the horse farms that border both sides of the road. Entering Medfield, make a sharp right onto Farm Street, where former 18th-century homesteads have been transformed into stylish properties. A left turn on Bridge Street will bring you into Sherborn. This is my favorite part of the ride, where the sprawling fields, faded red barns, and old stone walls remind me of Vermont. Another left onto Lake Street will leave you at the shores of Farm Pond, a large body of water hidden in the forest of maples and pines.
Complete the loop around the pond and make your way back to Dover and Farm Street, where you veer left. Continue onto Main Street and you will turn right onto Claybrook Road, beloved by all bikers in the region. Claybrook brings you back to Centre Street, where you can turn right to complete the loop or head left to cross the Charles River and keep on pedaling into Needham and beyond.