Best Motorcycle Roads & Destinations in Massachusetts, United States

If you are interested in going on a motorcycle trip somewhere within the United States, you may want to consider visiting Massachusetts or “the Bay State.” There is plenty of notable natural terrain to check out including the dense forests of the Berkshire Mountains, the New England Uplands, the Pioneer Valley, and the sandy beaches and massive bluffs of Cape Cod. You can also take your motorcycle to locations of historical significance such as the landing site of the Mayflower, battlegrounds from the Revolutionary War, and the location of the Salem Witch Trials.

If you are unsure where you would like to go, take a look over Massachusetts’s famous motorcycle roads and destinations. This article will also prep you on Massachusetts’s essential motorcycle laws. 

Distance: 133 miles
Time: 3 hours 14 minutes
Start: Gardner
End: Gardner

While you are still within Gardner, you can take the opportunity to explore locations such as Eaton Street, Perley Brook Reservoir, Gardner Museum, Dunn State Park, and Otter River Conservation Area. Departing westward from Gardner, you will come across Templeton State Forest, Warwick State Forest, and Wendell State Forest.

When you arrive in Greenfield, you can check out Poet’s Seat Tower, Murphy Park, and Highland Park. Continuing to head west, you will pass by Shelburne State Forest, and Shelburne Falls.

Transitioning onto Route 112, you will travel south along the left side of the loop. The only real notable places to look out for include Ridge Hill and Ashfield Lake. Turning eastward, you will have the opportunity to get meals at establishments such as the Ashfield Lake House and Pekarski’s Sausage. After you have passed South Deerfield, you will encounter Mt. Sugarloaf State Reservation.

Further along the bottom length of the loop, you will come close to Puffers Pond, Buffam Falls, Harkness Conservation Area, Shutesbury State Forest, Brooks Woodland Preserve, Swift River Reservation, and Mass Audubon’s Cook’s Canyon Wildlife Sanctuary. Returning to Gardner, you will head north via Route 68 which will take you beside Hubbardston State Forest and Hubbardston Wildlife Management Area. 

Distance: 63 miles
Time: 1 hour 34 minutes
Start: Athol
End: Templeton

Starting in Athol, you can take the time to explore Cass Meadow Conservation Area, Silver Lake Park, and Alan E. Rich Environmental Park. You will begin to head south via U.S. Route 202 which will take you close to Keystone Bridge, New Salem State Forest, Quabbin Overlook, and Shutesbury State Forest.

Reaching the middle length along the left side of the loop, you will start to curve around Quabbin Reservoir. You will get the chance to visit Pelham Overlook and will reach the southwest corner of the loop at Belchertown.

Traveling eastward via Route 9, you will travel along the bottom side of the loop which will allow you to check out the Swift River Wildlife Management Area and Quabbin Reservoir State Park.

Beginning to turn northwards towards Templeton, you will be able to check out Grenville Park, Babbitt Wildlife Sanctuary, and Phillipston Wildlife Management Area.

Distance: 72 miles
Time: 1 hour 42 minutes
Start: Williamstown
End: 184 Governor Dukakis Drive, Orange

Starting atop the Massachusetts-New York border, you will begin to head eastward which will take you through Taconic Ridge State Forest, Taconic Trail State Park, and Margaret Lindley Park. Arriving in Williamstown, you can check out the exhibits at Clark Art Institute and Williams College Museum of Art.

Continuing to make your way east, you will pass by Natural Bridge State Park, Windsor Lake Park, Historic Valley Park, Florida State Forest, Tannery Falls, Mohawk Trail State Forest, Better Place Forests Berkshires, Hail to the Sunrise Park, and Catamount State Forest before you arrive in Shelburne Falls.

Winding onward on Mohawk Trail, you will pass in between Montague Wildlife Management Area, Wendell State Forest, Northfield State Forest, and Warwick State Forest before arriving at the end of the route.

Distance: 29 miles
Time: 47 minutes
Start: New Marlborough
End: Southwick

Departing eastward from New Marlborough via Route 57, you will pass through or come close to several natural areas such as Sandisfield State Forest, Tolland State Forest, Clam River Reserve, Granville State Forest, and Granville Gorge.

Traveling through southern Massachusetts, the route will come relatively close to the Massachusetts-Connecticut border. It is recommended you travel this route during the fall thanks to the colorful foliage contributing to the amazing natural scenery.

Distance: 44 miles
Time: 1 hour 14 minutes
Start: Heath
End: South Deerfield

Starting close to the Vermont-Massachusetts border, you will head south via Route 8A. You will pass by HO Cook State Forest, Crowningshield Conservation Area, Pelham Lake Park before you arrive in Charlemont.

Continuing to travel southward along Route 8A, you will come close to Mohawk Trail State Forest and Kenneth Dubuque Memorial State Forest. You will then transition onto Route 116 as you complete the left side and southwest corner of the loop.

Traveling eastward along the bottom side of the loop, you will be traveling on long curves and sudden elevation changes through farmlands. If you wish, you can take slight detours that can take you to DAR State Forest and Conway State Forest as you make your way to South Deerfield. 

Distance: 31 miles
Time: 55 minutes
Start: Halifax
End: Marion Center, Marion

Departing from Halifax, you will begin to head southward via Route 105. Off the right-hand side, you may be able to make out Taunton River, Taunton River Wildlife Management Area, and Wildlands Trust - Great River Preserve.

When you arrive in Middleborough, you will have the chance to admire the exhibits at Robbins Museum of Archeology. You can also get a quick bite to eat at either Pizza Pirate, the Charred Oak Tavern, Central Cafe, or Boston Tavern.

You will finish going southwest via Route 105 then you will transition onto Route 18. You will ride southeast which will take you in between or beside Assawompset Pond, Tamarack Park, Long Pond, Great Quittacas Pond, Little Quittacas Pond, and Keene River.

Approaching the final leg of the route, you will be within the vicinity of Wildlands Trust - Rounseville II Preserve, Wildlands Trust - Lincoln P. Holmes Memorial Woods Preserve, Wildlands Trust - Stephen C.L. Delane Memorial Forest, and George E. & Katherine H. Church Wildlife Conservation Area as you finish getting to Marion Center.

Distance: 16 miles
Time: 42 minutes
Start: Gooseberry Island
End: Gooseberry Island

Starting off the Atlantic Coast, you will start to head north along the small peninsula as you make your way back to the mainland. Turning northeast, you will pass by Mass Audubon’s Allens Pond Wildlife Sanctuary as you travel along Horseneck Road.

Turning westward onto Hixbridge Road, you will cross Hix Bridge which will take you close to Westport. You will have the opportunity to check out the exhibits at Cadman-White-Handy House.

Turning southward via Main Road, you will pass by Dunham’s Brook Conservation Area. You will cross over Norman Edward Fontaine Bridge which will take you to Horseneck Beach State Reservation as you conclude the return trip to Gooseberry Island. 

Distance: 13 miles
Time: 18 minutes
Start: Townsend
End: Rudge State Road

Surrounding Townsend, you will have the chance to explore the surrounding natural areas including Meetinghouse Park, Squannacook Brook State Forest, and Townsend State Forest.

Heading westward, you will pass by Willard Brook State Forest. If you are interested in making a slight detour towards the south, you will also be able to check out Pearl Hill State Park.

Close to the end of the route, you will pass between Watatic Mountain State Wildlife Area and Ashburnham State Forest. When you find yourself on Rindge State Road, you will travel until you reach the edge of the Massachusetts-New Hampshire border.

Distance: 27 miles
Time: 51 minutes
Start: Knowles Beach
End: Knowles Beach

Heading westward from Knowles Beach, you will be within proximity to the Knowles Reserve and Paskamansett Park. Shortly after clearing Paskamansett Park, you will turn northward and will ride parallel to New Bedford Park. Traveling along the length of Chase Road, you will pass by Indian Cliff Estate and Sleepy Hollow.

Traveling westward along the top side of the loop via Old Westport Road, the only notable location to visit would be the University of Massachusetts Dartmouth. Turning south onto Fisher Road and Division Road, you will travel beside Destruction Brook Woods.

Along the southern side of the loop, you will clear several wide bends along Horseneck Road, Rock O’Dundee Road, and Potomska Road. In between Horseneck Road and Rock O’Dundee Road, you will curve around the northern tip of Slocums River. The rest of the way back to Knowles Beach will be largely uneventful as you head northward. 

Distance: 41 miles
Time: 1 hour 31 minutes
Start: Newbury Town
End: Rockport

Starting in Newburyport, you have the opportunity to grab a warm meal at either Michael’s Harborside, the Grog, Loretta, Mission Oak Grill, etc. You can also check out the exhibits at the Custom House Maritime Museum. Leaving Newburyport, you will begin to wind around southward via Route 1A.

You will ride in between Parker River National Wildlife Refuge and William Forward Wildlife Management Area. As you continue to wind through the wilderness, you will get to pass through the Mass Audubon’s Rough Meadows Wildlife Sanctuary. Leaving the natural areas behind, you will encounter Dows Basin and Daniel Boone Park along the way to Ipswich.

When you are within the vicinity of Wenham, you will have the chance to learn the history of the community at Wenham Museum or just check out the natural scenery at Wenham Lake. Arriving in Bethel, you will be able to spend leisure time at either Snake Hill, Green’s Hill, or Dana Street Beach.

Departing from Bethel, you will travel eastward via Route 127 along the Atlantic Coast. You will pass by Powder House Hill Reservation, Masconomo Park, Sweeney Park, Rafes Chasm Park, Ravenswood Park, and Stage Fort Park. You will then arrive at your final destination in Rockport. 

Distance: 37 miles
Time: 1 hour 21 minutes
Start: Taunton
End: City Point

Heading northward from Taunton, you will be close to Lincoln Woods, Wheaton Farm, Clifford C. Grant Reservation, Inter Lochen Park, Stoughton Memorial Conservation Land, and Shepherd Pond Conservation Area before you even make it to Canton.

Continuing to travel north, you can check out the exhibits at the Museum of American Bird Art at Mass Audubon. You will also pass by Pequit Brook, Memorial Field, Ponkapoag Pond, and Blue Hills Reservation.

For the last leg of the route, you will travel along the coast of the Boston Harbor. You will pass by Merrymount Park, Caddy Memorial Park, Squantum Marshes, Malibu Beach, Carson Beach, and M. Street Beach before you finally arrive in City Point. 

Distance: 21 miles
Time: 33 minutes
Start: Russell
End: Northampton

Heading northward from Russell, you will travel parallel to Westfield River as you travel on both U.S. Route 20 and Route 112. You will pass by Huntington State Forest shortly after you put distance between you and the small town of Huntington.

Transitioning onto Route 66, you will be close to Mass Audubon’s Lynes Woods Wildlife Sanctuary. As you draw closer to Northampton, you will catch sight of Northampton Community Gardens and Northampton State Hospital Memorial Park. You can also check out the exhibits on display at the Smith College Museum of Art.

In Massachusetts, every rider is expected to wear either a three-quarter or full-face motorcycle helmet, no exceptions.

Choosing to ride bareheaded puts your safety at risk, thus Massachusetts police are within their right to fine you for neglecting to buy a motorcycle helmet. 

Passengers in Massachusetts are subject to the same motorcycle helmet laws as the operators though there is no minimum age requirement to be allowed to ride.

The popular means of carrying your passenger is to install a pillion with handholds and footrests. Or you can install a sidecar if you want better protection for the passenger’s lower body. 

In Massachusetts, motorcycles must have been looked over at an authorized vehicle inspection at least once before June 1st.

During the inspection, test the integrity of the parts that help you be seen, steer, brake, and signal when riding a motorcycle. 

Motorcyclists can be penalized if they are caught lane splitting in Massachusetts.

If you need a reference providing a more thorough explanation of Massachusetts’s motorcycle laws, click on this link. 

Hopefully, this guide has made you even more eager to take your motorcycle out for a spin into Massachusetts. You will have the chance to decide for yourself if a road or destination lives up to the hype in person. There is also more of Massachusetts that you can explore, other motorcycle-friendly places that have not been mentioned in this article. Even if you think you have seen everything you wanted in Massachusetts in a single trip, you might find there are other sights worth checking out.