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Routes
Road cycling routes
United States
Massachusetts
Worcester County

Enfield Overlook loop from East Quabbin/Dana

Hard

4.6

(2230)

13,301

riders

Enfield Overlook loop from East Quabbin/Dana

04:29

94.2km

1,300m

Road cycling

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is right next to a parking lot.

Last updated: March 24, 2026

Waypoints

A

Start point

Parking

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1

34.1 km

Enfield Overlook

Highlight • Viewpoint

B

94.2 km

End point

Parking

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Way Types & Surfaces

Way Types

58.1 km

34.5 km

1.51 km

106 m

Surfaces

94.0 km

164 m

104 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 (350 m)

Lowest point (120 m)

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Weather

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Today

Wednesday 10 June

27°C

14°C

36 %

Additional weather tips

Max wind speed: 19.0 km/h

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Description

If you're looking for a challenging road cycling adventure that blends history with stunning reservoir views, the Enfield Overlook loop from East Quabbin/Dana is definitely worth your time. This difficult 58.5-mile (94.2 km) route packs in 4251 feet (1296 metres) of climbing, taking roughly 4 hours and 29 minutes to complete. It's a serious ride for experienced cyclists who appreciate varied terrain and a deep sense of place, offering a unique glimpse into Central Massachusetts' past.

What to expect on Enfield Overlook loop from East Quabbin/Dana

Expect a ride that constantly changes, from the "silky-smooth asphalt" of Quabbin Park Road near the Enfield Overlook, offering expansive water views, to the more rugged, varied surfaces of the East Quabbin area. You'll encounter old asphalt, broken pavement, and even crushed gravel, especially around places like Dana Common. The route winds through deep woods and past active farmlands, with significant climbs like those leading to Rattlesnake Hill, rewarding you with "breathtaking views across the reservoir". This mix of surfaces and elevation changes means you need to be comfortable with your road bike on less-than-perfect roads and ready for a workout.

Planning your visit

While specific parking for this exact loop isn't detailed, the Quabbin Reservoir area has various access points, with Gate 40 being a key entry for the East Quabbin section. Be aware that road surfaces vary significantly, with some sections less ideal for narrow road bike tires, so check conditions if you're planning a visit after heavy weather. The area is beautiful year-round, but spring and fall offer pleasant temperatures and vibrant foliage, making them ideal times to explore the historical remnants and scenic vistas.

  • Distance: 58.5 miles (94.2 km)
  • Elevation gain: 4251 feet (1296 metres)
  • Difficulty: difficult
  • Estimated time: 4 hours and 29 minutes

Nearby routes

Hard

26

Around the Quabbin Reservoir

05:01h

104km

1,320m

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