Wellesley and the surrounding area offers a bounty of natural beauty, and what better way to experience it all than on a bicycle, cruising down some of the most scenic roads of the metro-west area with fresh air in your face. Here are a few routes that can provide anyone who owns a bicycle with a fun, healthy, and memorable experience. Routes increase in length as one scrolls down. Click on their titles for interactive maps with directions!

  1. Winter Street Loop (9.65 Miles)

This route allows the casual cyclist to immerse themselves in much of the natural beauty Weston has to offer in just under ten miles. Winding through Bogle Street and Winter Street, two quaint roads carved through a lush neighborhood, and then later cutting through the entirety of Oak Street, which similarly offers magnificent views, this route pleases the eye in many ways over the span of just a few miles.

  1. Glen/South Loop (14.27 Miles)

This loop is the perfect introduction to Dover and Sherborn—two towns cherished among the cycling community for their beautiful roads set amidst an almost rural backdrop. As one pushes down Glen Road and South Street, they will undoubtedly notice the satisfying transition from suburbia to lush forest, yet the true highlight of this route is the two mile stretch connecting these two roads, in which one experiences the beauty found in the farms, rivers, and forests that Dover and Sherborn have to offer.

Views such as this can be seen on the Glen/South Loop. Photo Courtesy of Adam Juma.
  1. Dover Loop (15.89 Miles)

This route immerses the cyclist in all the charm Dover has to offer. From Dover center itself, a quaint, beautiful downtown area centered around a colonial town hall, to the outskirts of the town, where one finds themselves alone with Mother Nature, this loop truly has it all. To highlight a single street in this loop would be an injustice to the other half dozen that are equally as magnificent, and it is the many miles spent winding through the rural streets of Dover and Sherborn make it a worthwhile endeavor.

  1. Powisset Street Loop (17.91 Miles)

Despite the highlight of this loop being the lush miles of Powisset Street, a quiet stretch of road surrounded entirely by idyllic forest, it is difficult to complete this route without realizing that the journey was just as beautiful as the destination itself. One can experience the beauty of Dover while on Centre Street and Walpole Street, and later immerse themselves in one of the most majestic parts of Needham through the sparsely populated areas surrounding southern Chestnut Street and Summer Street. While Powisset Street gives this route its name, it is an ensemble of roads that make it such a special loop.

  1. Weston/Wayland Rail Trail Loop (18.77 Miles)

One of the most satisfying experiences one can have as a cyclist is speeding down rail trails, surrounded by nothing but natural beauty and open road ahead. This loop passes through the Mass Central Rail Trail, a slice of repurposed railroad that now serves as a bike path connecting the town centers of Wayland and Weston. In addition to this rail trail, this loop also offers a glimpse into Weston’s downtown, a lush town center filled with beautifully designed churches, as well as Oak Street and Ashe Street, which together create a magnificent stretch connecting Weston to Wellesley.

  1. Natick Rail Trail Loop (19.37 Miles)

Slicing through Lake Cochituate and surrounded by greenery, Natick’s Cochituate Rail Trail is a beautiful stretch and a highlight of this loop. However, the rolling hills, farmland, and forest surrounding Rice Road often prove to be equally as dazzling, and the long stretch of Old Connecticut Path connecting them together makes for a thorough exploration of the beautiful towns of Wayland and Weston. Together, these parts create a highly unique and pleasing experience.

  1. The Ultimate Dover Sherborn Loop (20.09 Miles)

It would be very difficult to explain everything this loop has to offer in a succinct paragraph, but I will try my best to highlight some of its charm. The stretch connecting Dover and Sherborn provides any cyclist with miles immersed in nature and rural beauty, and the quaint, colonial town centers nestled in the vast forests of these towns are equally as rewarding. Another highlight one is sure to notice is Claybrook Road, which is surrounded by a ravishing mix of river, forest, and farms. Overall, this route allows any cyclist to immerse themselves in the breathtaking views and unique experiences Dover and Sherborn have to offer.

Leave a Reply

Your email address will not be published. Required fields are marked *