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Chestnut Hill Ave

Chestnut Hill Ave was laid out in the early 1800's. At that time there was no Cleveland Circle or Commonwealth Ave., so the street mainly connected Brighton Center with Brookline to the south, passing through scenic but relatively unpopulated territory. It was originally called Rockland Street beginning in 1840, and didn't see the name change to Chestnut Hill Avenue until 1872 - most likely due to the construction of the new Chestnut Hill Reservoir around 1870.  The name Rockland may have come from the rocky ledges along the road.

Originally, the road did not align with Market St as it does today.  It began where Academy Hill Rd (formerly Rockland St) is.  The final section on the other side of today's park connecting to Market St wasn't actually built until the 1860's. 

1870 Map with Chestnut Hill Ave marked in red

1909 Map

Original Firehouse.  See the red circle section of the above map.

This firehouse was built in 1873 as part of the Brighton Fire Department before the Town of Brighton was annexed to the City of Boston.   Brighton's Engine 1 and Ladder 1 became Boston's Engine Company 29 and Ladder Company 11 on the day of annexation, January 5, 1874.  A fire later destroyed much of the original building and it is now the Veronica Smith Senior Center.  On December 20, 1929 the Firehouse was moved to new quarters at 138 Chestnut Hill Avenue.


1913 Firehouse Equipment with Brighton Center on the left

For more photos of the Chestnut Hill Ave Firehouses visit our Brighton Allston Firehouses web site


1927 Last Run of a horse-drawn fire engine in Boston on Chestnut Hill Ave opposite the firehouse.  The building on the right was removed in the 1970s for a parking lot for the adjacent bank

1907 Celebration next to the Firehouse of Brighton's 100 Year Anniversary

100th Anniversary celebration with the former Holton library in the background on Academy Hill Rd

For more photos and information on Brighton's 100th Anniversary celebration visit our Brighton 100th Anniversary web site

c1905 The Bennett school with an Annex in the rear.  See the blue oval area on the 1909 map above

The Bennett grammar school was built in 1873 at a cost of $140,000 and was considered one of the best made and most expensive expensive buildings in the city.  The  clock in the tower was a landmark in Brighton.  In the days when Brighton was a town and a great cattle mart, this clock did duty for a large population of market people. 

The school started out in 1847 in the old Town Hall on Washington St.  It was then known as the Harvard Grammar School.
the Harvard name was transferred to the school in Allston until then known as the Second GrammarIn 1861, the school was moved to where the Winship school now stands.  Stephen Hastings Bennett gave the land for the school in consideration of the naming of the school the Bennett School.  In 1873, the the town began the building of the Bennet School and the Firehouse on Chestnut Hill Ave.  They were completed after the town was annexed to Boston in 1874.

The original building was two stories in height, with a Mansard roof, and included seven rooms and a hall. In 1885, a building containing six rooms was erected in rear of the Grammar building, and four of the rooms are occupied by Grammar classes. This building is known as the Bennett Annex.  In the spring of 1892, two rooms were made out of the play rooms in the basement and fitted for a Manual Training shop and a School of Cookery. 
Bennett School building was occupied by Primary classes of the district at this point.

In 1924, there was a major fire in the school with extensive damage to the fourth floor and roof.  Unfortunately, the attractive mansard roof and towers did not survive.

The Bennett school closed in 1945 and in later years the building was owned by the VFW and currently the Shalow House

Bennett School

c1920 Bennett School

c1890 Bennett School Annex behind the main building.  Courtesy of Digital Commonwealth

Bennett School Fire Headline from the Boston Globe April 9, 1924

1953 Bennett School without the towers.  Note the Jenny Gas Station on the right

Fire Fighting Equipment in Front of the Bennett School

1892 Bennett School Students (courtesy of Digital Commonwealth)

Bennett School Students 1899

Bennett School Students Planting Tomatoes 1922

1895 Academy Hill Rd. Photo taken from in front of the library looking towards Chestnut Hill Ave.  The horse is on Chestnut Hill Ave.  The large house on the hill is the previous Brighton High School building

Nathaniel Jackson home at the corner of Academy Hill Rd and Chestnut Hill Ave. See the black oval area in the 1909 map above.

The first stockyard in Brighton was laid out next to the Bull's Head Tavern, an inn that stood on the site of 201 Washington Street, about a quarter of a mile east of Brighton Center.  The cattle pens probably stood on the flat land opposite the tavern (Nantasket Avenue, Snow, and Shannon Streets cross that acreage today), where a stream provided a convenient water supply for the livestock.  The Winship slaughterhouse for these cattle stood on the site of the Jackson home..

Nathaniel Jackson

Nathaniel Jackson is a descendant of Edward Jackson who was born in England in 1601 and was a Cambridge selectman and a member of the General Court in 1647.  Edward left land to Harvard College in his will.  Nathaniel was born in Stillwater, NJ in 1817 and came to Brighton as a young man to work with James Dana. Nathaniel was a prominent man in Brighton. For nearly thirty years he was director in the old Bank of Brighton, director in the Abattoir, trustee of the Holton Library and on the library's building committee.

The Jackson home was moved to 41 Winship St in 1932

c1950  The Jackson home land was used for the building of the Brighton Municipal Court building

c1900 Hathaway Mansion with Academy Hill Rd on the left.  See the green oval on the 1909 map above.

James Hathaway came to Brighton in 1859 and was in charge of the Cattle Fair Hotel grounds.  He was also involved  in cattle sales.  He represented Brighton in the State Legislature in the 1880s and was one of the largest owners of real estate in Brighton.  In 1898, he replaced an older building on this site with the present structure, which was designed by the prominent architect Julius Schweinfurth.


c1910 Hathaway Mansion

Before the Hathaway mansion, Elizabeth Rowell Thomson lived at this location and was a major contributor to the arts and philanthropic ventures.  For more information on Elizabeth, see our Woman of Vision article

BAHM Book.indd

c 1900 on the western side of Chestnut Hill Ave near Union St.  The towers of the Bennett School can be seen on the right.

75 Chestnut Hill Ave

2009 William Jackson Ave is on the left next to 81 Chestnut Hill Ave

2011  American Legion post next to the current firehouse.  This building has been replaced with a new development

c1930 New Firehouse at 138 Chestnut Hill Ave (Photo Credit - Boston Fire Historical Society)

2009  Cumberland gas station before the improvements

c1895 Aberdeen School at 186 Chestnut Hill Ave shortly after being built.  This building ceased being a school in the late 1920s when the larger Alexander Hamilton School at 198 Strathmore Road was opened

The Aberdeen school became an American Legion post in this 1932 photo

First Parish in Brighton Unitarian Church

From the Boston University paper "First Parish Church in Brighton" by Eunjeong Kim, December 13, 2016:

The First Parish Church in Brighton was established in 1744, at the northeast corner of Market and Washington streets in Brighton Center. In 1808, moving across Washington Street, a larger and more elaborate church replaced the original building, where it also took on the function of Brighton’s first Town Hall.  With the church in need of repairs, the parish committee decided in 1890 to build a new church at a new location.  The church was sold for $16,000 and the lot for the new building on Chestnut Hill Ave was bought for $10,000 from Sarah E. Waugh and the heirs of William Warren.  Ground was broken for the new church in 1895.  Stone was blasted from the lot and used in the construction of the walls.  A 1821 Paul Revere bell from the old church was installed in the new belfry.  The church disbanded in 1941 and the building was leased to the Bethesda Lodge of Masons.  In 198
1, the building was sold to  the American Buddhist Shim Gum Do Association.

Alexander Hamilton Grammar School at Strathmore Rd (courtesy of the Boston Public Library). 
Replaced the smaller Aberdeen School at 186 Chestnut Hill Ave.

1909 Map showing the Aberdeen school and the First Parish church.  Development in this area was only beginning in 1909

Home of Daniel Waugh at the intersection of Chestnut Hill Ave and South St. 

The Waugh house was built by John Baker in the early 1700s.  His son Benjamin was a Sergent in the Revolutionary War.  Daniel Waugh became the owner in 1833.  His son Daniel was the Superintendent of the Evergreen Cemetery on Commonwealth Ave.  His daughter Sarah was a teacher in the primary, grammar and high schools of Brighton.

Below are some excerpts from "Historical Brighton Vol1" by J.P.C Winship pages 99-102 related to this area and house.  Refer to the 1885 map below.

"It is claimed that a very long time ago the present principal thoroughfare, from Newton Centre to the village of Little Cambridge (Brighton), entered the Reservoir grounds somewhere near Lake Street and followed closely the driveway on the west of the Reservoir and leaving the Baker Land entered the Winships woods (near today's Commonwealth Ave and South St) - better known to the older people as the "Sunday School Walk" from a custom of the Unitarian Sunday School having yearly in the summer time a "walk" as it was called from the Church to the woods."

Historical Brighton : an illustrated history of Brighton and its citizens "The road on Leaving the Baker land entered the Winship woods near Commonwealth Avenue, thence past the old house, which more than a hundred years ago stood near Strathmore Road, wound through the woods and around the ledges, to avoid hills, and came out on the direct load to the village, above or below the ledge on Chestnut Hill Avenue— indications
point below. The village at that time contained a school-house, a variety store, a blacksmith's shop and a few dwelling houses. The Brown ancestors reached the main road through a lane in front of the house; the Bakers, by a lane which connected with the road near the present Commonwealth Avenue. A narrow lane connected the two houses. Benjamin Baker found the route to the village too circuitous and, as an experiment, he made the first cart-path over the high hill in front of where the Unitarian Church now stands. "It is not known today what the owners of the land on the other side of the hill thought of his plan. On one side of the new path, the Winships owned the whole sweep of land to the village and beyond. But the path once opened continued ever after to be used; and year by year the town reduced its height and filled up the ravine on the other side till the hill has reached its present level and become the principal thoroughfare to Newton Centre, while the course of the old roads, through years of
disuse, cannot even be traced."

Waugh House with Chestnut Hill Ave on the right of the photo

1885 Map showing the location of the Waugh house at the bottom center.

1910 Commonwealth Ave at the Chestnut Hill Ave intersection.  Chestnut Hill Ave on the right goes down to Cleveland Circle.  The large house on the right is located inside the circle on the 1909 map below. 

1909 Englewood Ave on the left and Cleveland Circle in the distance on the right

1909 Looking up Chestnut Hill Ave from Beacon St in Cleveland Circle.  The MDC pool today would be on the left.  Notice how rural the area still is.

1909 Map with Comm Ave on the left and Beacon St and Cleveland Circle on the right. 

Englewood Ave on the left with Chestnut Hill Ave in the foreground (courtesy of Joel Shield) after the construction of apartment buildings

1875 Map showing the Reservoir road connecting with Chestnut Hill Ave. 

Chestnut Hill Reservoir Arch looking towards Chestnut Hill Ave. 

The arch is located inside the circle on the 1875 map above,  Looking through the arch in this photo, Englewood Ave would be to the right.  The view through the arch highlights the newly developed houses in the Aberdeen area that are on the 1909 map above.  This was before the development of the many apartment buildings in this area in the early 1900s. The Arch and Reservoir road were unfortunately removed when Commonwealth Ave was built in the 1880s.

s & Links

  1. Woman of Vision
  2. Firehouses
  3. Brighton Center
  4. Brighton Cattle Industry

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