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Routes
Bike touring routes & trails
United States
Massachusetts
Norfolk County
Brookline

Brookline to Gregg Conservation Land via South Street & Jamaica Pond loop

Routes
Bike touring routes & trails
United States
Massachusetts
Norfolk County
Brookline

Brookline to Gregg Conservation Land via South Street & Jamaica Pond loop

Moderate

3.0

(6)

88

riders

Brookline to Gregg Conservation Land via South Street & Jamaica Pond loop

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

A

Start point

Train Station

Get Directions

1

2.25 km

Jamaica Pond

Highlight • Lake

The lake is beautifully framed by mature trees and even has a boathouse for rowers and sailors. The entire approach to the arboretum is so picturesque that you almost forget you're in the middle of a big city.

Translated by Google •

Tip by

2

11.6 km

Cutler Park Reservation

Highlight • Natural

From here, you can enter Cutler Park Reservation, an area of over 700 acres of parkland that stands to protect the largest remaining freshwater marsh on the Charles River.

Whilst …

Tip by

3

16.0 km

South Street

Highlight (Segment) • Trail

This relatively flat and winding road guides you through lush green scenery, passing by Farley Pond and offering views of the Charles River.

Tip by

4

19.7 km

Gregg Conservation Land

Highlight • Forest

As you ride through this area, you can enjoy the beautiful scenery. The lush and dense green forest spans 42 acres, with some open areas exclusively designated for walking. It's a pleasant resting spot to appreciate the surrounding area.

Tip by

B

42.7 km

End point

Train Station

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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

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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.

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Frequently Asked Questions

Is this a loop route?

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.

How can I access the starting point of the route, and is parking available?

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.

What is the terrain like for touring cyclists on this route?

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.

What kind of scenery can I expect on this touring bicycle route?

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.

What are the main points of interest along the route?

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.

Does the route intersect other well-known paths?

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.

What is the best time of year to cycle this route?

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.

Is this route dog-friendly?

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.

Do I need a permit or pay an entrance fee for this route?

No, there are no specific permits or entrance fees required to cycle this route, as it primarily utilizes public streets and accessible conservation lands.

Are there facilities like water fountains or restrooms along the way?

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.

Are there any specific cycling regulations to be aware of, especially around Jamaica Pond?

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.

Where can I find refreshments or cafes near the route?

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.

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