The best places to bike in Brookline



Due to the pandemic, our daily lives have shifted drastically, leaving us with little time to adapt. Outdoor activities have gained popularity, and biking has been one of the them.

I have biked all across Brookline, Boston, Cambridge and Newton, and I have come upon so many amazing places. The locations that were my favorite were deeply serene, which is something that I, and I think most people, deeply need in these troubling times. Here are some of my top recommendations.


Jamaica Pond

This is the only location on this list outside of Brookline. If you want to bike somewhere just for a wide serene view of the water without heading to the sea, Jamaica Pond is the perfect destination. Biking is prohibited on the trail but nothing is stopping you from walking your bike near the water. I love the calmness of the area, specifically by the large boathouse located on the Jamaica Plain side. Be careful of the local swans though, they are giant and not friendly.



The Brookline Reservoir

The first of two in Brookline, the town’s titular reservoir does not disappoint. Once again, biking is prohibited upon the main trail, but walking is allowed and it is quite easy to bike to the side shown above on the top left through Dudley Street. The calmness of the water and the Resevoir’s tiny watchtower contrast well with the bustling Route Nine that runs right next to it. I personally recommend sitting on the edge of the little watchtower out upon the water, as it has a great view of the lake close to the water.


The Riverway/Emerald Necklace

Skirting the eastern side of Brookline, the Emerald Necklace is the best way to get to Fenway, and then further into Boston, without the use of major roads. The Riverway segment is both calm and active, with the river running the whole length and joggers constantly using the trails on both sides. I love using the Riverway as a nice opener to a more intense bike ride, as its relative calmness is reassuring at the beginning of a longer, more physically draining bike ride.



Chestnut Hill Reservoir

The second of the two reservoirs in Brookline, this one is even larger and more relaxed than the first. It is also a hub of sorts, great for bicyclists looking for a scenic gateway to Newton. The sheer size of the Reservoir is what truly makes it unique. I love taking a long walk around the whole trail, as the lane is long enough to socially distance, and it is a nice reward after a more intensive bike ride.






Holy Transfiguration Monastery

An obscure Greek Orthodox nook in south Brookline, the Holy Transfiguration Monastery covers a large ideal campus including a long idyllic field in the front and a tranquil forest in the back. The forest is full of small shacks with religious idols, which adds a rustic, but also somewhat adventurous, vibe to the area. However, the priests and workers there are friendly and love visitors, and they even have a goat named Andy that you can pet!



Fischer Hill Park

Perched above the steep Fisher Hill by the Runkle Elementary School, Fisher Hill Park is simple yet beautiful. The main field at the center of the park is surrounded by a brick watchtower on one side and a sloping trail on the other, with a wooden perch (as seen above) looking down on it. I can attest that after a calm ride around the outside trail, biking down Fisher Avenue is a very exhilarating experience.





Larz Anderson Park

The best place in Brookline to view a sunset, Larz Anderson Park has a lot to offer for bicyclists, especially in the evening. Easily accessible from the high school via Lee/Clyde street on the other side of the Brookline Reservoir, Larz Anderson is nestled in south Brookline and is far away from the urban north part of town. The large hill that marks the tallest point of the park is the best place in all of Brookline to catch a sunset, with the sun being visible for longer than normal due to the height of the hill. In all my time biking around Brookline, I found no better place to go to on a nice Friday evening bike ride than to Larz.

This article was updated to include a correction on 3/13/21