The Riverway, designed by famed landscape architect Frederick Law Olmsted, is a tranquil park that serves as a border between Boston and Brookline.
This route will take you to Landmark Centre, Fenway Park and Kenmore Square:
Grab a bike at the Brookline Village - Station Street @ MBTA station.
Head northeast on Pearl Street, then turn left onto Brookline Ave.
This will connect you to the Riverway path, where you will turn right and follow it north for about 0.8 miles until you reach the Landmark Centre. The 1929 art deco building serves as a hub for professionals, students and tourists. Here, you can dock your bike at the Landmark Centre Hubway Station and grab a bite to eat.
When you’re ready to continue, pick up another bike at Landmark Centre station and head up Brookline Ave, making a circle around Fenway Park by taking a right at Landsdowne Street and hugging Fenway until you come back around to Brookline Ave.
Follow Brookline Ave up to Kenmore Sq / Comm Ave Hubway station. Here you can drop off your bike and explore Kenmore Square on foot, taking in the iconic Citgo sign that is the main landmark of this area, often appearing in the backdrop of Red Sox games. Boston University is also nearby, as well as Lansdowne Street, a center for Boston nightlife.
The total distance of this route is about 2.5 miles. If you decide to ride it without stopping for a break, it should take you about 20 to 30 minutes.