Brookline Loop and JFK Birthplace

Boston, Massachusetts

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The fiercely independent town of Brookline has resisted Boston’s sprawl for over 300 years, persevering even as the city, block by block, annexed adjoining towns like Brighton, Roxbury, and Jamaica Plain. This ride explores Brookline’s enviable greenery, hills, and cultural sites, cutting from Amory Park near Back Bay through Coolidge Corner to the idyllic Larz Anderson Park. You’ll hook back north via the Brookline Reservoir and Aspinwall Hill, passing the preserved headquarters of famed landscape architect Frederick Law Olmsted as well as the birthplace of John F. Kennedy. By the end of this ride, you’ll have no doubts about why its larger neighbor has a right to be jealous.
Best Bike Rides Boston

DESCRIPTION FROM:

Best Bike Rides Boston

by Shawn Musgrave (Falcon Guides)

The fiercely independent town of Brookline has resisted Boston’s sprawl for over 300 years, persevering even as the city, block by block, annexed adjoining towns like Brighton, Roxbury, and Jamaica Plain. This ride explores Brookline’s enviable greenery, hills, and cultural sites, cutting from Amory Park near Back Bay through Coolidge Corner to the idyllic Larz Anderson Park.

You’ll hook back north via the Brookline Reservoir and Aspinwall Hill, passing the preserved headquarters of famed landscape architect Frederick Law Olmsted as well as the birthplace of John F. Kennedy. By the end of this ride, you’ll have no doubts about why its larger neighbor has a right to be jealous.

© 2014 Shawn Musgrave/Falcon Guides. All Rights Reserved.

Activity Type: Mountain Biking
Nearby City: Boston
Distance: 8.7
Trail Type: Loop/Lollipop
Duration: 1-1.5 hours
Local Maps: USGS: Boston South and Newton quads; DeLorme: Massachusetts Atlas & Gazetteer, p. 41
Driving Directions: Directions to Brookline Loop and JFK Birthplace

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Apr 2018