Past Walking Tours

Growing up Kennedy

What was it like to grow up as a Kennedy in Brookline?

On this one-mile walk through John F. Kennedy’s boyhood neighborhood, we’ll begin at his birthplace, 83 Beals Street and walk through the neighborhood to the second home the family moved to in 1920. On the way, we’ll learn about the early years of the Kennedy family, including JFK’s competitions with his older brother, parental expectations, childhood pranks and more! The walk will last about 30 minutes; participants are also welcome to join rangers for a tour of 83 Beals Street before or after the walk.

Frederick Law Olmsted Annual Summer Solstice Evening Walk

Frederick Law Olmsted National Historic Site is offering its annual summer solstice evening walk. This year, "A Short Walk on a Long Day" features Frederick Law Olmsted's Brookline historic neighborhood.

Led by a National Park Service ranger, this leisurely two- hour tour starts on the front circular drive at Frederick Law Olmsted National Historic Site, 99 Warren Street, Brookline, at the corner of Dudley Street. The walk takes place rain or shine and is free and open to the public.

No advance reservations are required.

For directions and more information on this tour and other programs, please call Frederick Law Olmsted National Historic Site at 617-566-1689, Monday - Saturday between 9:00 am and 4:30pm.

Lost Pond Walk

Meet at Skyline Park off Newton Street in South Brookline. Families welcome to join Brookline GreenSpace Alliance and Friends of Lost Pond to explore Brookline’s quaking bog.


Wear long sleeves and pants with socks.

North Brookline Walking Tour - Street Tree Identification

GreenSpace Environmental Learning Walk

Learn to identify at least 10 tree species in one hour. Hugh Mattison, BGSA Board member and chairman, Brookline Tree Planting Committee, will lead a 1-mile walk along residential streets.

The goal is to explain key characteristics (shape, bark, seeds, flowers, and leaves) of common Brookline street and park trees.

See website for more details:

150 Years of Shopping in Coolidge Corner

Meet: Kiosk at the Inbound Coolidge Corner T Stop

Led by: Ken Liss of the Brookline Historical Society

Distance: Approximately 1/2 mile

Coolidge Corner was home to just one store— Coolidge & Brother — from the 1850s to the 1890s. Following the widening of Beacon Street in 1887-88 and the arrival of the S.S. Pierce store a few years later, a major new shopping district took root. Almost all of the existing buildings in this still thriving commercial area were built between 1890 and 1930. Journey back to the initial development of the Coolidge Corner business district and get a glimpse of local shopping in the early decades of the 20th Century.

Blake Park: History of a Neighborhood

Meet: Brookline High School, 115 Greenough Street

Led by: Ken Liss of the Brookline Historical Society

Distance: Approximately 1 mile

In 1880, banker Arthur Welland Blake engaged Frederick Law Olmsted to draw plans for the subdivision into roads and lots of the Blake family estate on the lower part of Brookline's Aspinwall Hill. Olmsted's plans were never executed, and the estate remained something of an anomaly; a large tract of open land renowned for its landscaping in the heart of a community rapidly developing as a "streetcar suburb". Learn how the neighborhood of “Blake Park” finally emerged — despite failed plans, untimely deaths, and financial scandal — four decades after it was first conceived.

Frederick Law Olmsted Birthday Celebration:

The High Street Hill Association will present Frederick Law Olmsted Birthday Celebration in Olmsted Park! Co-sponsored by HSHA’s Friends of Leverett Pond, the Town of Brookline’s Parks and Open Space Division and the Brookline GreenSpace Alliance, the event will provide something for everyone in the family— a park stroll with Mr. Olmsted (actor Gerry Wright), sidewalk chalk art, music, glitter tattoos, nature stories, a pooch parade and a tree identification walk with Town Arborist Tom Brady— all topped off with an Olmsted birthday cake.

Free and open to all. Come to Olmsted Park’s Allerton Overlook near the intersection of Pond Avenue and Allerton Street.

The Beaconsfield Terraces: "An Experiment in Domestic Economy"

Explore the Beaconsfield Terraces, on the south side of Beacon Street between Dean Road and Tappan Street, one of the more unusual developments to follow the creation of the Beacon Street boulevard in the 1880s. Built by Eugene Knapp, a wool merchant, in the early 1890s the terraces were a residential complex in which people owned their units but shared ownership of a 6-acre park, stables, a playhouse (known as the Casino), tennis courts, a playground, and a central heating plant. A bell system connected the houses to the stables so that people could call for their horse and carriage. Today, only the residential buildings (Richter, Frances, Marguerite, Fillmore, Gordon, and Parkman Terraces) remain. This free one-hour tour is presented by Ken Liss of the Brookline Historical Society. Approximate time and distance: one hour and one mile.

Winter Tree Identification Walk

As part of Brookline's Climate Week (, Town Arborist Tom Brady, will lead us on a tree identification walk in Riverway Park.

Take the challenge of identifying trees without the presence of leaves.

Consider the contribution of trees to a healthy environment.

Meet at Longwood MBTA stop on the Riverside green line

Let us know you’re coming! Sip hot chocolate while you enjoy Olmsted's Emerald Necklace. (BGSA will provide the beverage if you bring your mug)