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My Ten Favorite Streets to Walk in Jamaica Plain

Last updated on May 3, 2021

Alex Cox recently accomplished an amazing feat — he walked every single street in Boston.


Cox is currently a Master in Urban Planning candidate at the Harvard Graduate School of Design. He recently achieved his long-term goal to visit every street in Boston by foot or by bike, and holds the Guinness World Record for fastest time to travel to every MBTA station. A long-time resident of the Fenway-Kenmore area, he now lives in Somerville. Here are his 10 favorite streets to walk in Jamaica Plain:

Jamaica Plain has always held a special place in my heart, because it was the first neighborhood of Boston that I ever lived in. While staying with family in Hyde Square just after moving to the city, I would walk the eastern length of Centre Street to Jackson Square each day to take the Orange Line to my new job, and look forward to stopping into Brendan Behan for a pint on my way home.

Now, having recently accomplished my goal of walking or biking every street in Boston, I’d like to share with you some of my personal favorite streets that I’ve walked in JP.

Forest Hills Street

Forest Hills Street (Photo by Alex Cox)

I enjoyed walking Forest Hills Street because of the contrast between the dense tree canopy of the “Wilderness” section of Franklin Park and the apartment buildings which look out upon it. If you had to distill the character of Boston’s built and natural environments into one street, you’d be hard-pressed to find another one where you can see triple deckers on one side and giant Roxbury puddingstone boulders on the other.

Heath Street

Although the imposing brick façades of the John R. Alley Brewery (pictured above) and the redeveloped American Brewing Company building technically sit just across the border in Mission Hill, a walk down Heath Street offers a fascinating glimpse into Jamaica Plain’s lost Victorian brewing history.

Bismarck Street

Bismarck Street (Photo by Alex Cox)

Looking ahead to Jamaica Plain’s contemporary brewery industry, the cozy quarters between the former Haffenreffer Brewery buildings (which today house the Boston Brewing Company and other tenants of the Jamaica Plain Neighborhood Development Corporation) and these historic apartment buildings harkens back to a period in America’s urban history when industry and manufacturing weren’t quite so segregated from residential areas.

Roanoke Avenue

Roanoke Avenue (Photo by Alex Cox)


Even though the hill is a little steep to walk up, I always enjoyed looking at the beautiful Victorian homes along this street when traveling between Centre Street and the Green Street T station.

Moss Bank Footway

I’m a big fan of public pedestrian paths with their own dedicated street signs. The Moss Bank Footway in Jamaica Hills is a prime example, offering a lovely car-free route between Moss Hill Road and Louders Lane.

Eliot Street


Eliot School (Photo by Alex Cox)

Although I enjoyed walking along many of the beautiful streets between Pond Street and Centre Street, Eliot Street was probably my favorite due to the presence of historic buildings like the Eliot School and the Ellen Swallow Richards House. The short dead-end streets along Eliot and Burroughs streets offered the opportunity to see many lovely old homes in a pastoral setting. 


As a cyclist and pedestrian I feel much safer traveling along the newly-rebuilt section of the Arborway east of Forest Hills, but I liked the tiered nature of these houses on the Arborway’s residential frontage road which back onto Hampstead Lane. I bet they get excellent views of the Arnold Arboretum.

Marbury Terrace

There are a lot of lovely residential streets that branch off from Amory Street in the Egleston Square area, but Marbury Terrace takes the cake for me because of this house’s excellent autumn decorations.

Parley Avenue

You never know what you’ll find tucked away on the hilly corners of Boston’s neighborhood. Just 600 yards from the Orange Line and only a block away from the hustle and bustle of Centre Street, the bucolic dirt roads of Parley Avenue and Parley Vale made me feel like I’d been transported to the countryside of Jamaica Plain past.

Sheridan Street

And finally, the climb up the hill to Sheridan Street and Cranston Street is worth it for these lovely views of downtown at dusk! Follow it up with dinner at one of Hyde Square’s excellent local restaurants.

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