Massachusetts road guide
The best motorcycle roads in Massachusetts, from the Berkshires to the Cape
The best motorcycle roads in Massachusetts are out west: the Mohawk Trail, the climb up Mount Greylock, Jacob's Ladder on US 20 and hilltown roads like MA 112 and MA 57. Closer to Boston, Cape Ann, the South Coast and Cape Cod give you the water. Here are 13 classics, with where each runs, why it's worth it, what to watch for and the best season.
- Roads listed
- 13
- Regions
- 3
- Highest road
- Mount Greylock summit
- Peak color, west
- Early to mid October
Before you pick
How to use this list of the best motorcycle roads in Massachusetts
Massachusetts riding gets better the farther you get from Boston. East of Worcester, the roads are busy, patched and full of rotaries. West of the Connecticut River, the Berkshires and the hilltowns stack up climbs, river valleys and small towns with almost no traffic on a weekday. The coast has its own appeal, with harbor towns, salt marshes and the long arm of Cape Cod, as long as you time it around the beach crowds.
The 13 roads below are grouped into three regions: the Berkshires, the hilltowns and the Quabbin, and the coast. Most riders pick two or three from one region for a day. Seasonal roads like the Mount Greylock summit road close in winter, so check before you go. For timing by region, see the best time to ride a motorcycle in Massachusetts. For regions, laws and events in one place, start at the Massachusetts motorcycle rides hub.
The Berkshires
The Berkshires: the Mohawk Trail, Greylock and the valley roads
- 1. Mohawk Trail (MA 2)Why: The classic Massachusetts ride. West of Greenfield, MA 2 climbs past Shelburne Falls, follows the Deerfield River through Charlemont, tops out near Whitcomb Summit and drops into North Adams through the famous Hairpin Turn, then on to Williamstown. Watch for: The Hairpin is very tight, so brake early and watch for cars stopped at the overlook. MA 2 is also a truck route, and foliage weekends are packed. Best season: June to mid-October, with early to mid October for color, ideally on a weekday.
- 2. Mount Greylock (Notch Road and Rockwell Road)Why: The road to the highest point in Massachusetts, about 3,491 feet, with the Veterans War Memorial Tower and a view across several states. Climb Notch Road from the North Adams side and come down Rockwell Road toward Lanesborough, or the reverse. Watch for: Narrow lanes, hikers and cyclists, rough patches, fog and a real temperature drop at the top. The summit roads are seasonal, so check the reservation's status first. Best season: Late spring to mid-October.
- 3. Jacob's Ladder Trail (US 20)Why: US 20 between Lee and Russell is a designated scenic byway that climbs over the Berkshire hills through Becket and Chester. Steady curves, deep woods and very little traffic midweek. Watch for: Frost heaves, patched pavement, logging trucks and deer. Best season: May to October.
- 4. US 7 through the BerkshiresWhy: US 7 runs the length of the Berkshires, from Sheffield through Great Barrington, Stockbridge, Lenox and Pittsfield to Williamstown. More scenic than twisty: town greens, mountains on both sides and good food at every stop. MA 183 past Stockbridge and Lenox makes a quieter parallel. Watch for: Town center traffic, summer concert crowds around Lenox and leaf peepers in October. Best season: May to October.
- 5. MA 23, Great Barrington to OtisWhy: A wooded road across the southern Berkshires from Great Barrington through Monterey to Otis, with lakes, small towns and good curves on the long grade above Great Barrington. Watch for: Deer at dusk, lake traffic near Otis on summer weekends and sand in spring. Best season: May to October.
Hilltowns and the Quabbin
The hilltowns and the Quabbin: quiet roads between the valleys
- 6. MA 112, Huntington to the Vermont lineWhy: MA 112 runs north from Huntington through Worthington, Goshen and Ashfield, crosses the Mohawk Trail and continues through Colrain to the Vermont border. Hills, curves, farms and some of the least crowded country in the state. Watch for: Sand at intersections in spring, frost heaves, farm equipment and long gaps between gas stations. Best season: June to October.
- 7. MA 9, Northampton to PittsfieldWhy: West of Northampton, MA 9 climbs through Williamsburg, Goshen and Cummington, crosses the high country around Windsor and drops to Dalton and Pittsfield. A steady, scenic way across the hilltowns. Watch for: Commuter traffic near both ends, deer, and weather that turns faster on the high ground. Best season: May to October.
- 8. MA 57, Southwick to New MarlboroughWhy: MA 57 heads west from Southwick through Granville, past Granville Gorge, then through Tolland and the back country of Sandisfield toward New Marlborough. Tight, wooded and quiet. Watch for: Narrow lanes, blind corners, deer and very few services once you leave Southwick. Best season: May to October.
- 9. MA 202 along the Quabbin ReservoirWhy: MA 202 runs north from Belchertown along the west side of the Quabbin, the huge reservoir that flooded four towns in the 1930s, through Pelham and New Salem toward Orange. Long, wooded and empty. Add the Quabbin Park road off MA 9 for the dam and the lookouts. Watch for: Long open stretches where your speed creeps up, and deer. Best season: May to October.
The coast
The coast: Cape Ann, the South Coast and Cape Cod
- 10. Cape Ann (MA 133 and MA 127)Why: MA 133 runs through Essex past the salt marshes and clam shacks into Gloucester, and MA 127 loops around Cape Ann through Rockport, Pigeon Cove and Annisquam. Harbor towns, granite and ocean on almost every bend. Watch for: Narrow streets, heavy summer traffic, tight parking in Rockport and pedestrians everywhere. Best season: May, June, September and October.
- 11. MA 88 to Horseneck Beach, WestportWhy: On the South Coast near the Rhode Island line, MA 88 runs south from US 6 through Westport's farm country to Horseneck Beach, with a side run to the fishing village at Westport Point. Open, flat and pretty, with farm stands and salt air. Watch for: Beach traffic on summer weekends, crosswinds and sand near the beach, and slow farm vehicles. Best season: May to October.
- 12. MA 6A, the Old King's HighwayWhy: MA 6A runs along the bay side of Cape Cod from Sandwich through Barnstable, Yarmouth Port, Dennis and Brewster toward Orleans, past old captains' houses, marshes and antique shops. Slow and pretty, and a far better ride than the Mid-Cape Highway. Watch for: Village speed limits, pedestrians, cars pulling out of shops and summer traffic. Best season: May, June, September and October.
- 13. US 6 on the Outer Cape to ProvincetownWhy: Past Orleans, US 6 runs up the Outer Cape through Eastham, Wellfleet and Truro to Provincetown, with the Cape Cod National Seashore, dunes and water on both sides near the end. Watch for: Crosswinds on the open stretches, sand on the road, heavy summer traffic and crowded, narrow streets in Provincetown. Best season: May, June, September and October.
Link them
Massachusetts rides that link the best roads
- The Greylock and Mohawk loopFrom the Northampton area, ride MA 9 west across the hilltowns to Pittsfield, take US 7 north to Lanesborough and climb Mount Greylock on Rockwell Road. Come down Notch Road into North Adams, then ride the Mohawk Trail east over the Hairpin to Greenfield and back south. A full day, and it closes on itself.
- The southern Berkshires loopFrom Great Barrington, ride MA 23 east to Otis, head south on MA 8 to Sandisfield, then take MA 57 west through New Marlborough back toward US 7. Check the connectors with the loop builder first, since some hilltown roads turn to gravel.
- The Cape Ann loopMA 133 brings you in through Essex, and MA 127 with its partner MA 127A circles Cape Ann from Gloucester through Rockport and back. Ride it early on a weekday in June or September and you'll have most of it to yourself.
Summary
Massachusetts motorcycle roads at a glance
| Road | Region | Best season |
|---|---|---|
| Mohawk Trail (MA 2) | Berkshires | Jun to mid-Oct |
| Mount Greylock summit roads | Berkshires | Late spring to mid-Oct, seasonal |
| Jacob's Ladder Trail (US 20) | Berkshires | May to Oct |
| US 7 | Berkshires | May to Oct |
| MA 23 | Southern Berkshires | May to Oct |
| MA 112 | Hilltowns | Jun to Oct |
| MA 9, Northampton to Pittsfield | Hilltowns | May to Oct |
| MA 57 | Hilltowns | May to Oct |
| MA 202 and the Quabbin | Central | May to Oct |
| Cape Ann (MA 133, MA 127) | North Shore | May to Jun, Sep to Oct |
| MA 88, Westport | South Coast | May to Oct |
| MA 6A | Cape Cod | May to Jun, Sep to Oct |
| US 6, Outer Cape | Cape Cod | May to Jun, Sep to Oct |
In the app
Massachusetts roads riders have added in Rippin'
Below are the Massachusetts roads riders have added to Rippin', pulled live from the app. Rippin' started in Southern California, and many states have only a handful of roads so far, so most of the classics on this page are still open for someone to add.
Adding one is simple. Ride it with Rippin' recording, open Segments and tap Create a Segment, then drop a start gate and a finish gate and trace the line. A person on the Rippin' team checks every road before it goes live, and your name stays on it. Riders who ride through it land on its board, and the crown goes to the rider who owns the road. It's about who rides the road, not who rides it fastest: Rippin' never rewards speed on public roads. Read more on segments and leaderboards and how roads get added.
Loops like the Greylock and Mohawk ride also claim turf: the land inside a loop that closes on itself becomes yours on the live map, and empty land is free to claim.
Live from the app
Massachusetts on Rippin' right now.
3 upcoming events and 0 rider-added roads in Massachusetts on the map today. This list updates whenever the site is rebuilt; the app always has the latest.
- Sun Nov 1Blue Knights MA 1 42nd Annual Toy RideRaynham
- Sun Nov 8Hope for the Holidays Toy Drive/Toy RunChicopee
- Sat Jan 16Autoparts Swap 'N Sell 2027West Springfield
No Massachusetts roads are in the app yet. Add the one you love from Segments and a person on our team checks it before it goes live. How roads get added.
FAQ
Questions riders ask.
What is the best motorcycle road in Massachusetts?
The Mohawk Trail on MA 2 is the classic, with the Hairpin Turn above North Adams. Add the Mount Greylock summit road and MA 112 through the hilltowns for a full western day.
Can you ride a motorcycle up Mount Greylock?
Yes, the summit roads are open to motorcycles in season. They close in winter, so check the reservation's status before you go, and expect hikers, cyclists and a colder summit.
Where are the twisties in Massachusetts?
West of the Connecticut River: the Mohawk Trail, MA 57 west of Southwick, MA 112, MA 23 and Jacob's Ladder on US 20. The eastern half of the state is flatter and busier.
What's a good motorcycle ride near Boston?
Head north to Cape Ann on MA 133 and MA 127, or south to the South Coast and MA 88 in Westport. Go early, because coast traffic builds fast on summer weekends.
Is Cape Cod good for motorcycle riding?
Yes, if you time it. MA 6A and US 6 on the Outer Cape are beautiful in May, June, September and October. In July and August, the bridges and the towns are very slow.
Can I add a Massachusetts road to Rippin'?
Yes. Ride it with Rippin' recording and use Create a Segment. A person on the Rippin' team checks it before it goes live, and your name stays on it.
Put a Massachusetts classic on the map.
Download Rippin' free, ride one of these roads with it recording and add it. Your name stays on it.
Free on iPhone and Android. How Rippin' works
