The Berkshires loop worth doing from Pittsfield climbs Mount Greylock on Rockwell Road, drops the north side on Notch Road into North Adams, then runs Route 8 south through the mill towns and comes back over US 20 and US 7. Greylock is the highest point in Massachusetts at 3,491 feet, and its auto roads are seasonal, open mid-May through the end of October. Everything else on the loop is open year-round. Plan a full day, and check the summit road dates before you build the ride around them.
Why the Berkshires ride differently from the rest of Massachusetts
Two things separate this corner of the state. The first is vertical relief: Greylock stands about 2,000 feet above the Hoosic Valley floor, and the roads that climb it are purpose-built scenic auto roads rather than through routes, so they are narrow, tight and slow on purpose. The second is that the valley roads underneath are old industrial corridors. Route 8 is the main highway between Pittsfield and North Adams, and it runs through Adams, Cheshire and Dalton at a working pace with real towns attached.
The combination is what makes a loop here better than an out-and-back. You get a genuine mountain climb, a fast valley return, and a set of southern Berkshire roads that are quieter than anything on Route 2.
Loop at a glance
| Base town | Pittsfield or Lanesborough |
|---|---|
| Summit | Mount Greylock, 3,491 feet, the highest point in Massachusetts |
| Climb roads | Rockwell Road from Lanesborough in the south, Notch Road from North Adams in the north |
| Valley leg | Route 8, which runs 66.6 miles (107.2 km) across Massachusetts from the Connecticut line to the Vermont line |
| Return leg | US 20 through Becket and Lee, then US 7 north through Lenox |
| Time | A full day with the summit stop; longer if you add the southern Berkshire roads |
| Season | Greylock auto roads open for the 2026 season 16 May to 30 October; the rest of the loop is year-round |
| Restriction | Vehicles over 22 feet long are prohibited on the Greylock auto roads and at the summit |
Send the climb leg to your navigation with this Pittsfield to North Adams directions link, then drag the route onto Rockwell Road and Notch Road so it goes over the mountain rather than around it on Route 8.
Rockwell Road, the southern climb
Start at the visitor center on Rockwell Road in Lanesborough, about a mile and a half off Route 7. It opens daily from 9am to 4pm and closes on Thanksgiving and Christmas, and it is the place to confirm road status before committing to the climb. Note that the visitor center itself stays reachable by all vehicles even when the upper auto roads are shut.
Rockwell Road is the longer and gentler of the two approaches. It is a two-lane scenic road with tight radius corners, frequent shade, and a surface that collects grit and leaf litter through the season. Speed limits are low and enforced, and the road is shared with hikers crossing to the trail network, which includes about 70 miles of paths and an 11.5-mile section of the Appalachian Trail. Ride it as a sightseeing climb, not a hill route.
The summit holds the Veterans War Memorial Tower, which opens for the season in late May and runs daily through mid-October, weather permitting. According to the Department of Conservation and Recreation page for Mount Greylock State Reservation, sight lines from the peak can reach as far as 90 miles on a clear day. There is also a hike-in primitive campground on Sperry Road about two miles from the summit, which is worth knowing about but is not a motorcycle-accessible site.
Notch Road, the northern descent
Notch Road is the older of the two routes to the top; the first automobiles reached the summit this way in 1902. It is steeper, narrower and shadier than Rockwell, which means it dries more slowly and holds frost later in the year. Descending it northbound into North Adams is the sensible direction, because the surface is more predictable going down than the alternative of arriving at the tightest corners already climbing hard.
Two things to plan around. The upper section can be in cloud when the valley is clear, and the temperature difference between Lanesborough and the summit is regularly ten degrees or more. Second, the 22-foot vehicle length restriction on both auto roads means you will meet fewer RVs than on comparable summit roads elsewhere, but the ones you meet will be occupying the entire lane on a blind corner.
Route 8 south and the southern Berkshires
From North Adams, Route 8 runs south through Adams, Cheshire, Dalton, Hinsdale and Becket, meeting US 20 in Becket. Across Massachusetts the route covers 66.6 miles from the Connecticut line at Sandisfield north to the Vermont line at Clarksburg, and the Pittsfield-to-North-Adams portion is the busiest part. It is not a technical road. It is a fast, open, well-surfaced valley run that gets you south efficiently with the Hoosac Range on one side.
Where it gets interesting is the turn west onto US 20 toward Lee, the road long known as Jacob's Ladder. From Lee, US 7 runs north through Lenox and Pittsfield to close the loop. If you have time, the detours worth taking are Route 183, which covers 31.9 miles (51.4 km) through Berkshire County from the Connecticut line to US 7 and US 20 in Lenox, and the roads through Beartown State Forest, a 12,000-acre forest around Benedict Pond in the Monterey and Great Barrington area. Both are quieter than anything on the northern half of this loop.
Fuel, weather and enforcement
Fuel is straightforward on the valley legs: Pittsfield, Adams, North Adams, Dalton, Lee and Great Barrington all have stations. There is none on either Greylock auto road, and no services at the summit beyond the seasonal facilities. Fill before the climb.
The weather pattern here is the one that catches out visitors. The Berkshires generate their own cloud, and a clear morning in Pittsfield can put you into fog at 3,000 feet by mid-morning. Autumn is the best riding and the worst traffic; foliage weekends from late September through mid-October fill Route 2, Route 7 and the Greylock roads with slow-moving cars. Spring brings frost heave damage on the secondary roads, which does not get repaired until later in the season.
Enforcement in the small Berkshire towns is real, particularly on the 30 and 40 mph stretches of Route 8 and US 7 through village centers. Check MassDOT's Mass511 travel service for construction before you leave; bridge and culvert work on the secondary Berkshire roads is common through the summer season.
Gear notes for a Berkshires day
The altitude change here does something specific to tires. Riding from a valley at 1,000 feet to a summit at 3,491 feet, on a cool morning, will drop your cold pressures measurably by the time you are at the top, and it happens on exactly the road where you want steady grip. Our explainer on why tire pressure falls in cold weather covers the mechanism, and a Bluetooth TPMS sensor set shows it happening rather than leaving you to guess at the summit car park with a gauge you left at home.
The other thing worth having is a display you can read in the deep shade of Notch Road and again in full sun on Route 8. A bar-mounted motorcycle riding system handles that range better than a phone screen, and the JADO S6 riding system keeps the loop's turn-by-turn on one screen through the whole day.
For the roads immediately north of here, see the Mohawk Trail guide, which connects to this loop at North Adams. The Boston day rides overview shows how far west this sits from the city, and the New England four-road guide covers the neighbouring mountain routes in Vermont and New Hampshire.
FAQ
When are the Mount Greylock auto roads open?
Seasonally. For the 2026 season the Department of Conservation and Recreation lists the auto roads as open from 16 May through 30 October, with the summit tower opening from late May. Dates shift year to year and with weather, so confirm on the state page before riding out.
Can motorcycles ride to the Mount Greylock summit?
Yes, when the auto roads are open. The posted restriction is on length, not vehicle type: anything over 22 feet is prohibited on the auto roads and at the summit. There is no motorcycle-specific ban and no toll.
Which way should you ride the loop?
Up Rockwell Road from Lanesborough and down Notch Road into North Adams. Rockwell is the gentler climb and Notch is the road you would rather descend than attack, and this direction also puts you on Route 8 heading south with the afternoon light behind you.
How long does the Berkshires loop take?
A full day if you stop at the summit, which almost everyone does. The climb and descent alone are slow going by design, and the southern legs on US 20 and US 7 pass through enough village centers that averaging highway speeds is not realistic.
Is there fuel on Mount Greylock?
No. There are no fuel services on either auto road or at the summit. Fill up in Lanesborough, Pittsfield, Adams or North Adams before starting the climb.
