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United States
Massachusetts
Berkshire County

Rockwell Road – Mount Greylock loop from Lanesborough

Routes
Road cycling routes
United States
Massachusetts
Berkshire County

Rockwell Road – Mount Greylock loop from Lanesborough

Hard

3.4

(20)

78

riders

Rockwell Road – Mount Greylock loop from Lanesborough

04:17

75.4km

1,650m

Road cycling

Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride. The starting point of the route is accessible with public transport.

Last updated: January 14, 2026

Tips

Temporary access restrictions

Includes segments with temporary access restrictions.

After 34.8 km for 244 m

Customers only

Waypoints

A

Start point

Bus stop

Get Directions

1

4.25 km

Rockwell Road

Highlight (Segment) • Cycleway

2

17.8 km

Mount Greylock

Highlight • Summit

Mount Greylock is the tallest peak in Massachussets. On a clear day, you can see up to 90 miles in the distance.

At the peak, there is a visitor center, restrooms and a scenic viewing area.

Tip by

3

37.4 km

Hoosic River

Highlight • River

The beautiful Hoosic River runs through three states and is fed by streams from the Green Mountains of Vermont, the Taconics of New York and the lofty sides of Mount …

Tip by

B

75.4 km

End point

Bus stop

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Way Types & Surfaces

Way Types

54.0 km

15.4 km

5.99 km

< 100 m

Surfaces

73.1 km

2.01 km

264 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 (1,050 m)

Lowest point (180 m)

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Weather

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Today

Wednesday 24 June

23°C

12°C

0 %

Additional weather tips

Max wind speed: 18.0 km/h

to get more detailed weather forecasts along your route

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Description

If you're looking for Massachusetts' ultimate road cycling challenge, the Rockwell Road – Mount Greylock loop from Lanesborough delivers. This difficult 46.8-mile (75.4 km) road cycling route packs a serious punch with 5403 feet (1647 metres) of elevation gain, typically taking around 4 hours and 17 minutes to complete. It's a demanding ride best suited for experienced cyclists ready to tackle significant climbs and enjoy panoramic rewards, making it one of the best road cycling Massachusetts Mount Greylock area options.

What to expect on Rockwell Road – Mount Greylock loop from Lanesborough

The journey begins with the iconic Rockwell Road ascent from Lanesborough, a continuous climb that averages 4.5% to 6.1% but includes stretches over 10% grade. As you pedal upwards, you'll pass through the unique "ecological island" environment of Mount Greylock State Reservation, resembling a Canadian boreal forest. Keep an eye out for several scenic vistas along the way, including the Adams Overlook, before reaching the 3,491-foot summit. Here, the Mount Greylock Veterans War Memorial Tower stands tall, and on a clear day, you can see up to 70 miles across five states. The descent, especially if you loop via Notch Road, is described as a thrilling roller coaster, requiring caution and reliable brakes. This route is definitely for advanced cycling routes Mount Greylock enthusiasts who appreciate both a physical test and stunning natural beauty.

Planning your visit

Planning your ride is key for this challenging loop. The Rockwell Road Scenic Byway, your primary ascent, is typically open from mid-May to November 1st, so plan your trip within these months. Temperatures at the summit can be significantly colder than at the base, so bringing a windbreaker for the descent is a smart move. Check the Mount Greylock cycling weather forecast before you head out, especially for autumn foliage bike ride Mount Greylock conditions, as views are best on clear days.

Trail details

  • Distance: 46.8 miles (75.4 km)
  • Elevation gain: 5403 feet (1647 metres)
  • Difficulty: difficult
  • Estimated time: 4 hours and 17 minutes

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