Boston neighborhood Digital Guide

Recommendations from Off The Beaten Path Food Tours including our Official Tasting Spots. Trust us, they're worth a visit.

View Guide By Neighborhood:
+ Fenway
+ Jamaica Plain
+ Roslindale

Fenway, Boston

Two polaroids showing a mural at Fenway Park and the famous Citgo sign. 

Boston, Massachusetts is the capital of Massachusetts: it is home to over 700,000 in a state of 7 million people. The population density is high and only growing, and one area that has exploded in the 2000’s is the Fenway neighborhood. Part of the Emerald Necklace park system, Fenway is only about 1.25 square miles but is home to many area college students from Boston University to Simmons.

The name “Fenway” comes from the word “fens” which is a British term for low, marshy area. When the area marshland was filled in under the direction of Frederick Law Olmsted who also designed New York’s Central Park, the area was divided in multiple sub-neighborhoods. 

The city’s famous Citgo sign sits over by Commonwealth Avenue in Kenmore Square. Nearby, Fenway Park was opened the same year the Titanic sunk in 1912. As you wander the streets down Brookline Avenue, you’ll see Fenway Green, the color of the park and nearby streets. Today Fenway is thriving, with not only new buildings in development but also plans for a huge indoor arts center and one-acre park.

Jamaica Plain, Boston

Two polaroids showing Jamaica Pond and a platter full of chocolates.  

Jamaica Plain, Boston, MA is known as “JP” to the locals. It’s a known secret that JP has some of the tastiest and freshest food in Boston, but it’s a bit hidden from the “beaten path” destinations such as nearby Fenway Park. In fact, some JP residents want to keep it that way, and this tight-knit community is definitely keen on preserving its neighborly feel.

 A small city, JP is only 4.4 square miles and has 40,000 inhabitants. Today’s population of JP is extremely diverse, with many college students moving into its apartments starting in the 1990’s, and also one of the city’s largest hispanic populations of over 30% which is reflected in a lot of its food. 

The early inhabitants of JP were well-to-do farmers supplying vegetables and fruits to Boston and also home to the country estates of government officials, professional and literary men, and city merchants. Many Bostonians summered here. There’s two large pieces of land in JP that were designed by Frederick Law Olmsted (1822-1903) who also designed Central Park in NY and is widely considered the founder of landscape architecture. 

On one side of town is the world-famous Arnold Arboretum that is 281 acres of land and has thousands of trees, and the other is Franklin Park (first called West Roxbury Park), which is a large 527 acre natural park. That’s why Jamaica Plain was once described as the “Eden of America.” Up near Centre Street where we are now is Jamaica Pond.

Roslindale, Boston

Two polaroids showing Tony's Market and a cafe in Roslindale. 

Located in the City of Boston, Roslindale used to be covered by Roxbury which also included the area which is now Jamaica Plain and West Roxbury. Roslindale way back in 1630 when it was part of Roxbury was primarily used for farming at the time, and it wasn’t until the 1840’s that the residents started to work towards separating the towns.

Originally it was called “South Street Crossing” because of the name of its railroad station at South Street which is now where the Roslindale Village MBTA stop is. Roslindale was renamed after the town of Roslin in Scotland which also had similar geography including hills and valleys. It was named by John Pierce who said it reminded him of Roslin. He himself was born in England. He incorporated the use of the word “dale” which means open valley, which is in reference to the south where we have the Blue Hills. As Roslindale developed, so did its architecture and they built not only impressive large Victorian and Queen Anne homes but also smaller bungalows and 2 and 3 family houses. Today the town itself has around 34,000 residents currently and is rapidly growing and thriving.

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