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Routes
Road cycling routes
United States
Massachusetts
Norfolk County
Brookline

Coolidge Corner to Great Blue Hill via Stony Brook Reservation loop

Routes
Road cycling routes
United States
Massachusetts
Norfolk County
Brookline

Coolidge Corner to Great Blue Hill via Stony Brook Reservation loop

Moderate

2.7

(12)

80

riders

Coolidge Corner to Great Blue Hill via Stony Brook Reservation loop

01:59

35.7km

390m

Road cycling

Embark on the Coolidge Corner to Great Blue Hill via Stony Brook Reservation loop, a moderate racebike route that offers a substantial ride through varied scenery. This 22.2-mile (35.7 km) journey takes you from urban settings into the natural beauty of the Blue Hills Reservation, where you will gain 1265…

Last updated: April 23, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

West Roxbury Parkway

Stony Brook Reservation

Neponset River Reservation

Blue Hills Reservation

Waypoints

A

Start point

Parking

Get Directions

1

9.67 km

Bellevue Hill

Highlight • Viewpoint

And you can ride your bike right up to the Water Tower in Stony Brook. Not much of a view, but it's nice and peaceful.

Tip by

2

11.2 km

Turtle Pond

Highlight • Lake

When it’s nice weather kids with bikes will hang out here on the sandy beach, with grills and food and beer. When it’s icy, this is access to the icy surface of Turtle Pond!

Tip by

3

19.0 km

Great Blue Hill Summit

Highlight • Summit

Ride your bike up the Big Blue Hill, and get a few minutes rest, and the view as a reward!

Tip by

4

25.5 km

Dell Ave Rock Urban Wild

Highlight • Natural Monument

Dell Avenue Rock consists primarily of a puddingstone ledge arising approximately 40 feet above Hyde Park Avenue. There are some outcrops near the top of the rock. The site is …

Tip by

B

35.7 km

End point

Parking

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Way Types & Surfaces

Way Types

19.2 km

10.3 km

5.68 km

294 m

265 m

< 100 m

Surfaces

34.0 km

1.69 km

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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 (180 m)

Lowest point (10 m)

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Weather

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Today

Tuesday 26 May

28°C

13°C

0 %

Additional weather tips

Max wind speed: 16.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How long does it typically take to complete this cycling loop?

This moderate road cycling loop is approximately 35.7 km (22.2 miles) long and typically takes about 1 hour and 59 minutes to complete. This duration is an estimate and can vary based on your fitness level and how often you stop to enjoy the scenery.

What kind of terrain and surfaces can I expect on this route?

The route is primarily on well-paved surfaces, making it suitable for road bikes. However, be aware that some sections within Stony Brook Reservation, like the Gavin Path, might be overgrown with missing chunks of pavement, and the Overbrook Path has eroded pavement and water diverters that act as speed bumps. Within the Blue Hills Reservation, while many double-tracks are gravelly fire roads, this specific route sticks to mostly paved roads. You'll encounter significant grades, particularly on segments like Summit Avenue and Summit Road in the Blue Hills.

What are the main scenic highlights along the Coolidge Corner to Great Blue Hill loop?

You'll experience diverse scenery, from urban sections to the natural beauty of Stony Brook Reservation and Blue Hills Reservation. Notable highlights include the panoramic views from the Great Blue Hill Summit, offering extensive vistas of Boston and the south shore. Other points of interest include Bellevue Hill, Turtle Pond, and the Dell Ave Rock Urban Wild.

Is this cycling route suitable for beginners?

This route is generally considered a "moderate road ride" requiring "good fitness." While it's primarily on paved surfaces, the significant elevation gain of around 385 meters (1280 feet) and the presence of challenging climbs within the Blue Hills Reservation mean it's not ideal for absolute beginners. Cyclists should be reasonably fit to enjoy this loop.

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

The route can be enjoyed in various seasons, but spring and fall offer pleasant temperatures and beautiful foliage. Summer can be warm, so an early start is recommended. Winter cycling is possible, but be mindful of ice and snow conditions, especially on less-maintained sections or shaded areas.

Are dogs allowed on this cycling route?

This route is designed for road cycling, and while dogs are generally allowed in many parts of the Blue Hills Reservation and Stony Brook Reservation, they must be kept on a leash. However, cycling with a dog on a leash can be challenging and potentially unsafe on a road cycling route, especially given the traffic and varied terrain. It's generally not recommended for this specific type of activity.

Do I need any permits or pay an entrance fee for the Blue Hills Reservation or Stony Brook Reservation?

No, there are no specific permits or entrance fees required to access the Blue Hills Reservation or Stony Brook Reservation for cycling. Both are public parklands managed by the Massachusetts Department of Conservation and Recreation (DCR) and are freely accessible.

Where can I park or access the route if I'm not starting from Coolidge Corner?

While the route starts from Coolidge Corner, you can access it from various points, especially near Stony Brook Reservation or Blue Hills Reservation. Parking is available at several locations around both reservations. For example, there are parking lots within Stony Brook Reservation and at various trailheads in the Blue Hills. Check local DCR websites for specific parking lot locations and availability.

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

Yes, this route incorporates sections of several other paths. Notably, it covers a significant portion (36%) of the Claire Saltonstall Bikeway. You'll also find smaller segments that overlap with the Walking City Trail (Sections 1, 2, and 3), the Boston Marathon route, and the Pierre Lallement Bike Path.

Are there any cafes, pubs, or accommodation options along the route or near the start/end?

Coolidge Corner, the starting point, is a vibrant area with numerous cafes, restaurants, and shops. As you venture into Stony Brook and Blue Hills Reservations, amenities become scarce, so plan accordingly. However, there are options for refreshments and food in towns bordering the reservations, such as Hyde Park or Milton. For accommodation, Coolidge Corner and the surrounding Boston area offer a wide range of choices.

What makes this loop a good choice for interval training?

The varied terrain and significant climbs, particularly within the Blue Hills Reservation, make this route an excellent choice for interval training. The steep grades on segments like Summit Avenue (7.3%) and Summit Road (9.2%) provide natural challenges to push your limits, followed by flatter or downhill sections for recovery, allowing for an effective workout.

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