The Perfect Cycling Guide to Boston, MA

Located on the outskirts farthest from Boston in West Roxbury, this large suburban park is used for all manner of recreational activities. With over six miles (9.6 kilometers) of trails, it is a great location for cyclists of all skill levels. Because the park started as a landfill developed on wetlands, it is home to a large population of wildlife. At the highest points in the park, you’ll be able to catch a beautiful view of downtown Boston.

This 2.5-mile (four-kilometer) loop in West Cambridge offers a quick and easy workout. It’s accessible to West and North Cambridge via Alewife, and even from the Harvard area, if you’re willing to tack on a few miles to your trip. The scenic area surrounds a reservoir and includes trails through wooded areas and alongside a golf course. For some extra distance, combine the Fresh Pond Loop with a ride through nearby Danehy Park, which is just up the street.

This 10-mile (16-kilometer) bike path starts near Alewife Station in North Cambridge and travels north all the way to the suburban town of Bedford. The historic route is a rough estimate of the path traveled by the first American militiamen from the Revolutionary War. During the first battles of that war, the Minutemen—a nickname for early American soldiers—pushed their British opponents from Concord, MA, back south to Boston. This route also connects with four other nearby bike paths.

Located 10 miles (16 kilometers) south of Boston, this reservation is in the cities of Quincy, Milton, Randolph, and a few others. It is the largest section of undeveloped land in the Boston area. With a bounty of mountain trails, it offers a great challenge for bikers seeking an adventurous woodland ride. With several possible trail combinations—over 40 miles (64.3 kilometers) total—it can provide an intense challenge for experienced mountain bikers.

What started as an unpopular project in the 1960s to route Interstate 95 through the Jamaica Plain neighborhood eventually became this linear park that makes its way up to the edge of Boston’s South End. It totals nearly five miles (eight kilometers) in length. The Southwest Corridor is perfect for urban bikers seeking a convenient workout and can even double as a safe shortcut to work for those who live near it. This route intersects with the city’s Emerald Necklace series of parks at the Arborway in Jamaica Plain.

Franklin Park lies at the intersection of the neighborhoods of Dorchester, Roxbury, and Jamaica Plain. Its main path covers a little over two miles (3.2 kilometers), filled with peaceful woody areas. The Franklin Park Zoo is also located here. A bike ride through the park and a trip to the zoo can make for a perfect day. You can even pass the ruins of the zoo’s old bear cages.

This reservation in Hyde Park contains several trails within its wooded areas, covering anywhere between two and six miles (3.2–9.6 kilometers). It offers a peaceful stretch of nature within an urban area. Stony Brook is an ideal spot for a family bike ride, especially in the spring when the surrounding natural areas are in full bloom. All of the paths are relatively flat and very easy to navigate.