Cleveland Circle is a neighborhood in the Boston suburb of Brookline. Brookline is southwest of Boston and is easily accessible to downtown Boston with the T and MBTA buses. Cleveland Circle is located where Beacon Street meets Chestnut Hill Avenue. It was settled early as farm land, but really began to thrive when Beacon Street was completed in the mid 19th century. It reached its peak when the street cars brought the people from Boston out to enjoy the area. Today it has a young vibe and lots of places to eat and drink in the area.
While the official address of the Chestnut Hill Reservation is Chestnut Hill, it is located within a few hundred feet of the Cleveland Circle T stop and is an important part of this neighborhood. It is an outstanding urban park that has ample opportunities to enjoy the outdoors. The reservation is dog-friendly, and leashed pets are allowed. The park has walking and jogging trails, as well as a swimming pool and a skating rink. In the warm weather, fishing is allowed from the shore of the reservoir. This is a neighborhood treasure.
There are still many remnants of the development from the 19th century when lovely single-family homes dotted the area. You can still find some Queen Anne and Colonial homes, though these days many of them have been converted into apartments or condos. There are blocks of large apartment buildings to accommodate the workers who wanted to live within commuting distance of Boston.
The area around Cleveland Circle T stop is lively and filled with local restaurants and entertainment. A few chain stores also have branches in the neighborhood. These include CVS Pharmacy, Applebee’s Neighborhood Grill, Starbucks, and the New England favorite Dunkin’ Donuts.