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Routes
Road cycling routes
United States
Massachusetts
Norfolk County
Milton

Mattapan to Lake Massapoag loop

Moderate

2.6

(29)

49

riders

Mattapan to Lake Massapoag loop

02:20

56.5km

360m

Road cycling

Embark on the Mattapan to Lake Massapoag loop, a moderate road cycling route that spans 35.1 miles (56.5 km) with a total elevation gain of 1195 feet (364 metres). This ride offers a distinct shift from the urban streets of Mattapan to the serene, scenic landscapes around Sharon. You'll spend…

Last updated: April 23, 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

25.0 km

Lake Massapoag

Highlight • Lake

Beach St cuts across the north side of the lake, west/east. There are spots you can stop well off the road to admire the view and have a break.

Road …

Tip by

2

33.8 km

Crescent Ridge Dairy Bar

Highlight • Cafe

Crescent Ridge is a local dairy with locals fields and cows. This is a great place to stop if you riding around the area, for ice cream and other refreshing …

Tip by

B

56.5 km

End point

Train Station

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Way Types & Surfaces

Way Types

30.6 km

16.0 km

9.26 km

369 m

219 m

Surfaces

56.3 km

219 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 (90 m)

Lowest point (10 m)

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Weather

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Today

Thursday 28 May

22°C

12°C

77 %

Additional weather tips

Max wind speed: 19.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

What is the overall difficulty of the Mattapan to Lake Massapoag loop?

The overall journey is considered moderate to difficult for road cycling. While the loop around Lake Massapoag itself is easy, the connection from Mattapan involves navigating urban and suburban roads with traffic, which requires careful planning and confident riding.

How long does it typically take to complete this road cycling route?

Based on our data, the average duration for this 56.5 km (35.1 miles) racebike route is approximately 2 hours and 20 minutes. This can vary depending on your pace, traffic conditions, and any stops you make along the way.

Where can I park to start this cycling loop?

As this route combines urban and suburban roads, there isn't one designated trailhead parking lot for the entire loop. If starting in Mattapan, you'll need to find suitable street parking or public parking options in the area. For the Lake Massapoag section, parking is available near Memorial Park Beach in Sharon.

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

No, there are generally no permits or entrance fees required for cycling the public roads that make up this loop. While parts of the route may pass near or through areas associated with the Blue Hills Reservation, cycling on the public roads within or adjacent to it does not typically incur a fee. Always check for specific regulations if you plan to venture onto dedicated park trails.

Is the Mattapan to Lake Massapoag loop suitable for beginners?

The full loop, especially the urban sections from Mattapan, might be challenging for absolute beginners due to traffic and the need for assertive riding. However, the 6-mile loop directly around Lake Massapoag in Sharon is generally easy and suitable for all fitness levels, making it a good option for beginners if you start directly in Sharon.

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

Spring and fall offer the most pleasant cycling conditions with cooler temperatures and beautiful scenery. Summer can be enjoyable, but be prepared for warmer weather. Winter cycling is possible but requires appropriate gear and caution due to potential ice or snow, especially on less-trafficked roads.

What kind of terrain can I expect on this route?

The route primarily consists of paved roads. The Lake Massapoag loop is mostly flat with minimal elevation gain. The connecting roads between Mattapan and Sharon will have varying conditions, including some state highways, and you should be prepared for potential uneven surfaces, storm drains, and potholes in places.

Are there any cafes or places to stop for refreshments along the way?

Yes, the route passes by the Crescent Ridge Dairy Bar, which is a great spot for a break and refreshments. You'll also find various options in the towns you pass through, particularly in Sharon and Stoughton.

Does this route intersect with other well-known cycling paths?

Yes, this route briefly intersects with sections of the Neponset River Greenway near Mattapan. Further south, it also touches upon parts of the Bay Circuit Trail and the Claire Saltonstall Bikeway, though these may not always be suitable for racebike cycling.

Is the Mattapan to Lake Massapoag loop dog-friendly?

This route primarily uses public roads, so dogs are generally allowed if they are safely secured (e.g., in a bike trailer or basket) and adhere to local leash laws and regulations in any parks or public spaces you might visit along the way. Always ensure your dog's safety and comfort when cycling.

What are some scenic highlights or viewpoints along the route?

The most scenic part of the route is undoubtedly the loop around Lake Massapoag, offering pleasant views of the lake and passing by Memorial Park Beach. The transition from urban Boston to the more rural landscapes of southeastern New England also provides interesting visual contrasts.

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