Brookline to Gregg Conservation Land via South Street & Jamaica Pond loop
Brookline to Gregg Conservation Land via South Street & Jamaica Pond loop
3.0
(6)
88
riders
02:32
42.7km
270m
Cycling
This moderate 26.5-mile touring cycling loop connects Brookline, Jamaica Pond, and Gregg Conservation Land, offering diverse urban and natur
Last updated: February 26, 2026
Tips
Your route passes through a protected area
Please check local regulations for:
West Roxbury Parkway
Waypoints
Start point
Train Station
Get Directions
2.25 km
Highlight • Lake
Translated by Google •
Tip by
11.6 km
Highlight • Natural
Tip by
16.0 km
Highlight (Segment) • Trail
Tip by
19.7 km
Highlight • Forest
Tip by
42.7 km
End point
Train Station
Way Types & Surfaces
Way Types
26.6 km
13.9 km
1.55 km
383 m
197 m
< 100 m
< 100 m
Surfaces
40.1 km
2.13 km
429 m
< 100 m
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Elevation
Highest point (80 m)
Lowest point (0 m)
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Weather
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Today
Thursday 21 May
22°C
11°C
11 %
Additional weather tips
Max wind speed: 11.0 km/h
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This route was planned by komoot.
Yes, the "Brookline to Gregg Conservation Land via South Street & Jamaica Pond loop" is designed as a loop, bringing you back to your starting point.
The starting point of this route is accessible by public transport, offering a convenient option for cyclists. While specific parking details aren't provided, areas around the route, especially near Jamaica Pond, may have parking available, though it can be limited.
The route primarily features mostly paved surfaces, making it generally suitable for touring bikes. However, be aware that some segments may be unpaved and potentially challenging to ride. Around Jamaica Pond, while there are bike paths, cycling directly on the path immediately around the pond is often prohibited for pedestrians, so you might need to walk your bike in those sections. South Street is described as a relatively flat and winding road.
You can expect diverse and appealing scenery. The route takes you past the picturesque Jamaica Pond, framed by mature trees. Along South Street, you'll enjoy lush green views, including Farley Pond and glimpses of the Charles River. The Gregg Conservation Land section offers a ride through a dense, green forest. It's a blend of serene natural areas and accessible urban pathways.
Key highlights include the beautiful Jamaica Pond, known for its natural beauty and community events. You'll also pass through South Street with views of the Charles River, and experience the lush forests of Gregg Conservation Land. The route also connects several significant urban green spaces.
Yes, the route intersects with several other paths. Notable sections include parts of the Claire Saltonstall Bikeway, Blue Heron Trail, and the Bay Colony Rail Trail. You'll also encounter segments of the Jamaicaway Bikepath and various local streets like Walnut Street and Centre Street.
The route offers enjoyable cycling through much of the year. Given its blend of urban and natural settings, spring and fall often provide pleasant temperatures and beautiful foliage. Summer is also popular, especially around Jamaica Pond with its community events.
While specific rules for the entire cycling route aren't detailed, areas like Jamaica Pond and Gregg Conservation Land are generally dog-friendly, though leash rules and specific restrictions may apply in certain sections or on pedestrian-only paths. Always check local signage.
No, there are no specific permits or entrance fees required to cycle this route, as it primarily utilizes public streets and accessible conservation lands.
Yes, particularly around Jamaica Pond, recent multi-million dollar upgrades have included new drinking fountains and bottle fillers, improving amenities for users. Restroom availability may vary along the route, often found near parks or public facilities.
Yes, it's important to note that while Jamaica Pond has bike trails, cycling directly on the path immediately around the pond is often prohibited and primarily designated for pedestrians. You might need to walk your bike in these sections. Always observe local signage and regulations.
The route passes through urban areas, and there are cafes and other refreshment options available, particularly in the vicinity of Jamaica Pond and within Brookline. These areas are well-served with amenities for visitors.