2017 Historic Walking Tours

All tours are free to the public and are offered on dates shown. Tours last between 60 and 90 minutes and are canceled in case of heavy rain. No reservations are required, just meet the guide at the location listed.

All tours are held on Saturday at 11:00 a.m.  

Tour Date Location   Tour Date Location
May 13
Monument Square   July 29 Green Street
May 20 Sumner Hill   August 5 Woodbourne
May 27
Stony Brook   August 12 Jamaica Pond
June 3 Hyde Square   August 19 Monument Square
June 10 Green Street   August 26 Sumner Hill
June 17 Woodbourne   Sept 2 Stony Brook
June 24  Jamaica Pond   Sept 9 Hyde Square
July 1  Monument Square   Sept 16 Green Street
July 8  Sumner Hill   Sept 23 Woodbourne
July 15 Stony Brook   Sept 30 Jamaica Pond
July 22 Hyde Square    

Green Street
green-street-po-med-res.jpgLaid out in 1836, the street played a key role in Jamaica Plain’s development, functioning as a residential, commercial, and transportation conduit in the lives of the district’s residents. Although Green Street was subdivided as early as 1851 for stores, factories and houses, it was not extensively developed until the late 1870s with construction continuing until the early 1900s. The Bowditch School was completed in 1892, and early in the 20th century the United States Post Office moved from its location on Call Street at Woolsey Square to its new location at the corner of Green and Cheshire Streets.
Leaves from Southern Jamaica Plain Health Center, 640 Centre St.

Hyde Square
Learn about 1840s Hyde Square when German and Irish immigrants transformed the neighborhood with their businesses, schools, and institutions. See how in the early 1960s, Hyde Square changed again when Cuban, Puerto Rican, and Dominican immigrants transformed it into Boston’s first predominantly Hispanic neighborhood. This tour also takes us to the home of Maud Cuney Hare, a prominent music historian and one of only two black women students at the New England Conservatory of Music in 1890. You will also learn about the property currently housing the MSPCA’s Angell Animal Medical Center which was once a site of the Perkins School for the Blind. The tour will also walk through the Sunnyside neighborhood, the site of homes built by philanthropist Robert Treat Paine from 1889 to 1899 as a “worker’s utopia” for working families.
Leaves from Brendan Behan Pub, 378 Centre St.

Monument Square
Tour a residential area that includes a National Historic District. View architecture that spans three centuries; the oldest community theater company in the United States; and an elegant 18th-century mansion that once served as the country’s first military hospital. Learn about the monument that commemorates fallen Civil War soldiers from West Roxbury and about Pauline Agassiz Shaw who established the class that became the model for continuous free kindergarten education. We will visit a house dating to 1716 that once served as a tavern, the Eliot School dating back to 1689, the home of the first woman to graduate from MIT and the First Church Burial Ground.
Leaves from Loring-Greenough House, 12 South St.

Jamaica Pond

Once a district that only included the houses of Boston’s elite, the Pond later was put to industrial use as tons of ice were harvested there each winter. Learn about the movers and shakers such as Francis Parkman and James Michael Curley who made their homes on the Pond’s shores. Discover how the Pond was transformed from private estates and warehouses into the parkland we know today.
Leaves from the Bandstand, Pond St. and Jamaicaway.

Stony Brook

Explore a fascinating industrial area at the geographic heart of Boston that includes 19th-century tannery and brewery buildings, the homes of early German settlers, and today’s Boston Beer Company, the brewers of Samuel Adams. In the 1970s, a coalition of community groups joined together to block construction of the Southwest Expressway through Jamaica Plain and other Boston neighborhoods. Today, the Southwest Corridor Park that runs through the Stony Brook neighborhood stands as a testament to the power of community activism.
Leaves from Stony Brook Orange Line T station.

Sumner Hill

This National Historic District includes one of the finest collections of Victorian houses in the area. The district includes the ancestral home of the Dole Pineapple Company founder and the homes of progressives who were active as abolitionists and women suffragists.
Leaves from Loring-Greenough House, 12 South St.


This neighborhood developed from 19th-century summer estates into a model suburban enclave. It contains examples representative of New England architecture with designs by local architects and builders. It also contains an unusual garden city model housing development by the Boston Dwelling House Company which was founded in 1912.
Leaves from Bethel AME church steps, corner of Walk Hill and Wachusett Sts.