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Routes
Road cycling routes
United States
Massachusetts
Norfolk County
Milton

Mattapan to Willett Pond loop via Green Street

Moderate

3.4

(29)

99

riders

Mattapan to Willett Pond loop via Green Street

02:45

65.2km

500m

Road cycling

This moderate 40.5-mile road cycling loop from Mattapan to Willett Pond offers diverse scenery and takes about 2 hours and 45 minutes.

Last updated: February 26, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Blue Hills Reservation

Waypoints

A

Start point

Train Station

Get Directions

1

7.15 km

Green Street

Highlight (Segment) • Climb

Green St is a lovely little climb. It’s a narrow road with very little traffic, and tightly surrounded by pine trees. Something about the start reminds me of an Alpine …

Tip by

2

35.0 km

Willett Pond

Highlight • Lake

Willett Pond is a small lake with a small beach area where kayaking is also allowed. The residents of the 85 houses there are allowed to use the lake more, but also protect it. An exciting and good concept.

Tip by

B

65.2 km

End point

Train Station

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Way Types & Surfaces

Way Types

33.8 km

16.5 km

14.1 km

576 m

219 m

Surfaces

64.3 km

710 m

219 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 (110 m)

Lowest point (10 m)

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Weather

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Today

Thursday 21 May

22°C

11°C

0 %

Additional weather tips

Max wind speed: 8.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the terrain like for the Mattapan to Willett Pond loop via Green Street?

The primary cycling experience in this area, particularly originating from Mattapan, is the Neponset River Greenway Trail. This trail is predominantly a paved, multi-use path, making it ideal for road cycling. There is a short section (approximately 0.3 miles) between Granite Avenue and the MBTA Red Line overpass that is hard-packed, but still rideable for road bicycles. The route generally offers a relatively flat profile.

Is the Mattapan to Willett Pond loop suitable for beginners?

Yes, the Neponset River Greenway Trail, which forms a significant part of the cycling experience from Mattapan, is generally considered a low-stress, high-quality route. Its relatively flat terrain and dedicated car-free sections make it suitable for beginners and families. Some areas near Mattapan Square or along Truman Parkway might involve occasional traffic, but the greenway sections are designed for ease of use.

Where can I access the trail and find parking?

A highly accessible entry point for the Neponset River Greenway Trail is directly behind the Mattapan MBTA Station. This is a convenient starting point for exploring the area. Parking is available at various points along the Greenway, including near parks like Pope John Paul II Park. For those without their own bike, Bluebikes stations are also conveniently located along or near the Greenway.

What can I see along the Mattapan to Willett Pond cycling route?

Cycling this route, especially along the Neponset River Greenway, offers diverse scenery. You'll enjoy views of the Neponset River, marshlands, and parks like Pope John Paul II Park and Tenean Beach. The trail also passes historical sites, old industrial areas, and features public art. Notable features include the "basket-handle-style" Harvest River Bridge and boardwalks near Mattapan Square. While Willett Pond is a related feature in the area, the main route provides a tree-lined river valley experience. You'll also pass Green Street, which is noted as a climb.

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

The best time to cycle the Mattapan to Willett Pond loop, particularly the Neponset River Greenway, is typically from spring through fall. These seasons offer pleasant temperatures and vibrant natural scenery. While accessible year-round, winter cycling might be less comfortable due to colder weather and potential for ice or snow on the path.

Is the Mattapan to Willett Pond loop dog-friendly?

The Neponset River Greenway Trail, which is a key part of this route, is generally dog-friendly. Dogs are typically allowed on leash. Always ensure your dog is under control and that you clean up after them to maintain the trail's cleanliness for all users.

Are there any permits or entrance fees required for this route or Blue Hills Reservation?

No permits or entrance fees are generally required to cycle the Neponset River Greenway Trail or for general access to the Blue Hills Reservation. However, specific events or facilities within the reservation might have associated fees. Always check the official mass.gov website for the most current information regarding any specific regulations or fees for the Blue Hills Reservation.

Does this route connect to other trails?

Yes, the route, particularly through the Neponset River Greenway, is a crucial link in the regional trail network. It connects communities and parks along the Neponset River. While the specific "Mattapan to Willett Pond loop via Green Street" isn't a formally named intersecting trail, the general area is part of a larger network. The route also passes through sections of the Claire Saltonstall Bikeway (8%), Skyline Trail (4%), and Warner Trail (3%).

What kind of scenery and wildlife can I expect?

You can expect a diverse range of scenery, transitioning from urban settings to natural landscapes. Highlights include views of the Neponset River, expansive marshlands, and various parks. The trail offers a tree-lined river valley experience, providing a sense of escape. You might spot various bird species, especially in the marsh areas, and other small wildlife common to urban green spaces.

Are there places to eat or get refreshments along the way?

Given that the route starts in Mattapan and connects through various communities via the Neponset River Greenway, there are numerous opportunities to find cafes, pubs, and restaurants. Mattapan Square itself offers options, and as you cycle through Dorchester, Hyde Park, and Milton, you'll find local establishments near the trail for refreshments or a meal.

Is the Mattapan to Willett Pond loop a dedicated cycling path or shared with traffic?

The Neponset River Greenway Trail, which is the most prominent cycling route in this area, features dedicated paved, multi-use paths that are car-free for significant sections. This provides a safe and enjoyable cycling experience. However, some parts, particularly near urban centers like Mattapan Square or along roads like Truman Parkway, may involve sharing the path with pedestrians or navigating occasional traffic, requiring cyclists to be attentive.

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