Riding the Bay State
Massachusetts motorcycle rides: Berkshire climbs, hilltown roads and the coast
The best Massachusetts motorcycle rides are out west and on the water. The Berkshires have the Mohawk Trail, the climb up Mount Greylock and long valley roads, the hilltowns above the Connecticut River are quiet and twisty, and Cape Ann and Cape Cod give you the coast. Boston traffic is the price of admission. Here are the roads, the season, the helmet law and how to make every ride count with the free Rippin' app.
- Helmet law
- Required for all riders
- Lane splitting
- Not allowed
- Main season
- April to early November
- Highest road
- Mount Greylock
Why ride Massachusetts
Why Massachusetts is worth riding
Massachusetts has deep motorcycle roots. Indian started building motorcycles in Springfield in 1901, and riders here still treat the western half of the state as their playground. Get past Worcester and the traffic thins, the hills rise and the roads start to curve.
The Berkshires in the far west have the Mohawk Trail, Mount Greylock, US 7 and the Jacob's Ladder Trail. The hilltowns between the Berkshires and the Connecticut River are small towns linked by twisty two lane roads. Central Massachusetts is rolling hills and reservoirs. The North Shore and Cape Ann have salt marshes, fried clams and the loop around Gloucester and Rockport. Cape Cod has the Old King's Highway and the long run out to Provincetown.
Greater Boston is dense, with rotaries, heavy traffic and rough pavement. Most riders there treat the first hour as the commute to the good roads.
The roads
Best motorcycle roads in Massachusetts
- Mohawk Trail (MA 2)Runs west across the northern part of the state through the Deerfield River valley to North Adams and Williamstown. Long climbs, river views and the famous Hairpin Turn above North Adams. Take the Hairpin slow and watch for cars stopped at the overlook.
- Mount Greylock Summit RoadNotch Road from North Adams and Rockwell Road from Lanesborough climb to the summit of Mount Greylock, the highest point in Massachusetts, with a view across several states. Open seasonally. Watch for hikers, cyclists and a real temperature drop at the top.
- Jacob's Ladder Trail (US 20)US 20 between Lee and Russell climbs over the Berkshire hills on a designated scenic byway. Steady curves and little traffic. Frost heaves and patched pavement are common.
- US 7, the BerkshiresRuns north and south through Great Barrington, Stockbridge, Lenox and Pittsfield. More scenic than twisty, with classic New England towns and good food. Expect summer and foliage traffic through the town centers.
- MA 23, Monterey to Great BarringtonA wooded road across the southern Berkshires past lakes and small towns, with good curves on the way down into Great Barrington. Light traffic most of the year. Deer are common at dusk.
- MA 112, the hilltownsRuns north from Huntington through Worthington, Goshen and Ashfield toward the Vermont line. Quiet, hilly and curvy, through some of the least crowded country in the state. Sand at intersections in spring and few gas stops.
- MA 127 and MA 133, Cape AnnMA 133 runs through Essex past the salt marshes and clam shacks into Gloucester, and MA 127 loops around Cape Ann through Rockport and Annisquam. Ocean views and harbor towns. Summer traffic in Rockport is heavy and the streets are narrow.
- MA 6A, Old King's HighwayRuns along the bay side of Cape Cod from Sandwich toward Orleans, past old captains' houses, antique shops and marshes. A slow, pretty alternative to US 6. Village speed limits and summer crowds, so relax and enjoy it.
- US 6, Outer Cape to ProvincetownPast Orleans, US 6 runs up the Outer Cape through Wellfleet and Truro to Provincetown, with dunes and Cape Cod Bay on both sides. Crosswinds on the open stretches and heavy summer traffic.
When to ride
When is motorcycle season in Massachusetts?
Most Massachusetts riders run from April to early November. Eastern Massachusetts and the Cape warm up first and stay riding later. The Berkshires and the hilltowns are a few weeks behind in spring and turn cold earlier in fall, and the Mount Greylock road opens and closes with the season.
Fall is the best time. Foliage usually peaks in the Berkshires and along the Mohawk Trail in early to mid October and a little later toward the coast. Weekend leaf traffic on MA 2 and US 7 is heavy, so start early.
Summer brings humid days and thunderstorms, and Cape Cod traffic on summer weekends is a serious delay. Spring brings sand, salt and potholes from the freeze and thaw. Nor'easters and the remnants of tropical storms can hit the coast, especially from late summer into fall.
Laws
Massachusetts motorcycle laws: helmets and lane splitting
Helmets: Massachusetts requires a helmet for every rider and passenger, at every age. See the IIHS helmet law overview for how Massachusetts compares with other states.
Lane splitting and filtering: As of 2026, Massachusetts law doesn't allow lane splitting or filtering. Several states are changing their laws, so check before you ride.
This is a plain-English summary, not legal advice. Laws change, so check the Massachusetts statutes or DMV before you ride.
Events
Massachusetts motorcycle events
The biggest rally near Massachusetts is Laconia Motorcycle Week in New Hampshire, usually in June and an easy day's ride north. Americade in Lake George, New York, also usually runs in June. The Distinguished Gentleman's Ride runs worldwide each May. Check the organizer for dates.
Closer to home, the calendar is weekly bike nights at shops and bars, spring blessing of the bikes rides, charity rides through the summer and toy runs in late fall. In Rippin', open Meets to find them near you and RSVP. Repeating meets show their next date, and riders and shops can post events. See motorcycle events in the app.
Live from the app
Massachusetts on Rippin' right now.
0 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.
No Massachusetts events are on the Rippin' map yet. Know a bike night, rally or charity ride? Post it in the app under Meets, or have the organizer add it, and it shows up here and on the map for every rider nearby.
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.
Local knowledge
Massachusetts riding tips
- Learn the rotariesMassachusetts has a lot of rotaries. Yield to traffic already in the circle, pick your exit early, and watch for drivers who don't.
- Carry E-ZPass on the PikeThe Massachusetts Turnpike (I-90) uses cashless tolling. Without a tag you get a bill by mail.
- Time the Cape bridgesThe Bourne and Sagamore bridges are the only road onto Cape Cod, and summer weekend traffic backs up for miles. Cross early in the morning or midweek.
- Watch for frost heavesWestern Massachusetts back roads heave and crack every winter. Read the pavement on MA 112 and US 20 before you lean.
- Deer and mooseDeer are common across the state, and moose turn up in the northern Berkshires and central hills. Dusk is the danger window.
Rippin' in Massachusetts
The motorcycle app for Massachusetts riders
Rippin' is a free motorcycle app for iPhone and Android. Tap Record Ride once, pocket the phone, and get a Ride Wrapped recap with your map, miles, turf and points when you stop. See the free ride tracker.
Rippin' started in Southern California, so Massachusetts has few riders and roads in the app so far. The map is wide open. In Turf Wars, a loop that closes back on itself claims the land inside on the live map, and empty land is free to claim. A Berkshires loop over the Mohawk Trail and back down US 7 claims a big slice of the west.
Shops and cafes can become poker stops on the partners page, and riders can nominate stops; read how poker runs work. Add a favorite road with Create a Segment, and start a squad so your crew's chat, plans and turf live in one place.
FAQ
Questions riders ask.
What is the best motorcycle road in Massachusetts?
The Mohawk Trail (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 day out west.
When is motorcycle season in Massachusetts?
About April to early November. The Berkshires start later and end earlier, and fall foliage in early to mid October is the best riding of the year.
Is lane splitting legal in Massachusetts?
No. As of 2026, Massachusetts law doesn't allow lane splitting or filtering. Several states are changing their laws, so check before you ride.
Do you have to wear a helmet in Massachusetts?
Yes. Massachusetts requires a helmet for every rider and passenger. Check the current statute before you ride, since laws change.
Where are motorcycle events in Massachusetts?
Shops and bars run bike nights statewide, and Laconia Motorcycle Week in New Hampshire is a short ride north. Open Meets in the Rippin' app to see what is on near you.
Is there a free motorcycle app for Massachusetts riders?
Yes. Rippin' is free on iPhone and Android, records every ride, and lets you claim turf, play poker runs and find meets. Most of the state is still unclaimed.
Claim the Berkshires.
Download Rippin' free, ride the Mohawk Trail in a loop, and put your name on the map out west.