Historic Motorcycle Routes near Boston, MA

Jun 17, 2024

Boston is famous for its history, with names like Sam Adams, John Hancock, and Paul Revere, and events like the Boston Tea Party and the Battle of Bunker Hill.

But there's more to Massachusetts. Salem is known for its witch trials, and H.P. Lovecraft set many of his stories in the northern part of the state. If you want to explore America's past, grab a motorcycle rental and check out these historic motorcycle rides in Massachusetts.

1. Ride to Salem, Gloucester, and Annisquam Village

One-day trip — 70 miles one-way; 140 miles round trip

If you’re looking for a weekend getaway in Boston but don’t want to spend it stuck in traffic, take a Ride to Salem, Gloucester, and Annisquam Village. This route showcases the North Shore's beauty, including salt marshes, rocky coves, and beaches. You can also enjoy whale watching and deep-sea fishing.

Start with a 20-mile ride from Boston to Concord, where the American Revolutionary War began. Then, take Route 62 east-northeast through Reading, Danvers, and Beverly.

This 140-mile ride is perfect for a Massachusetts adventure. Explore Salem's witchcraft history, shop in scenic Gloucester, and visit the artisan shops in Rockport, a village in the Gloucester area.

2. Lynn Fells Parkway East

One-day trip — 10 miles

For a shorter, urban ride, try the Lynn Fells Parkway East route. Starting just 4.5 miles from Boston in Somerville, this route ends in Western Saugus.

Begin by heading north to Somerville, then take 28 North (Fellsway). This becomes Lynn Fells Parkway. At the split, stay right to continue on Lynn Fells Parkway East. Follow it for six miles to Breakheart Reservation in Saugus, then head back the same way.

The ride begins in dense suburbs and transitions into hills and rocky forests. The well-maintained two-lane highway offers a smooth ride with a modest speed limit. Watch out for two slightly lower manhole covers that might cause a jolt.

Both ends of Lynn Fells Parkway have lots of amenities, like Assembly Row and Route 1, with bars, coffee shops, and gas stations in Melrose.

3. Plymouth and the South Shore

One-day trip — 80 miles

The Plymouth and South Shore motorcycle route is perfect for history enthusiasts, covering 80 miles to visit New England's first English settlement in Plymouth. Start in Wayland, just 20 miles from Boston, and follow Route 27 south through Walpole, Sharon, and Stoughton.

This route offers charming small towns, beautiful lakes, and scenic shorelines. Plymouth itself is rich in history and features plenty of dining options, antique shops, museums, and the Plymouth Plantation. Additionally, Dave Perewitz’s cycle shop in Halifax is a must-visit for bikers.

Most of the route is smooth, but be cautious of rough pavement near Brockton. Route 6 can be congested in the summer, and Route 44, running along the shoreline, may have sand in the spring, making it a potential challenge for riders.

4. Through the Country to the Castle

One-day trip — 36 miles

Through the Country To The Castle is a motorcycle route you should have on your itinerary. It spans 40 miles of scenic country roads, mountains, and ocean views and ends at Castle Island in South Boston.

Start in Taunton. Take Exit 9 off 495 Bay Road. Head north on Bay Street for 12 miles, which becomes Washington Street. Merge left onto 138 North, then right onto Blue Hills Road.

In Blue Hills Recreation Area, bear right onto Chickatawbut Road, then left onto Wampatuck Road. Exit onto Willard Street Rotary, take Furnace Brook Parkway to Quincy Shore Drive, and follow MA-3A North. Make a slight left onto William T. Morrissey Boulevard, then take the first exit on William J. Day Boulevard to Castle Island.

This route offers beautiful country roads, farms, and lakes, transitioning to winding roads through Blue Hills Mountain with stunning views of Boston.

Want a Local to Bring These Historic Sites to Life?

Boston's historic routes connect some of America's most significant sites, from the birthplace of the Revolution in Concord to Plymouth's colonial heritage. Riders Share offers motorcycle experiences near Boston led by locals who know the roads through these historic towns and can show you routes most visitors never find. If you'd rather ride with someone who can point out what happened at each landmark than navigate the back roads on your own, a guided experience is a great way to connect the history to the ride.

5. Quabbin Reservoir Loop

One-day trip — 64 miles

The Quabbin Reservoir Loop will meet any Massachusetts traveler’s needs and more. It runs a good portion of Massachusetts, from Boston to Belchertown in the middle of the state.

Start this trip in Athol, then take Route 2 West and the South Exit. Follow it to Route 9 outside Belchertown, then take Route 9 East to Windsor Dam. Pass Ware, take Route 32 North to Gilbertville, and continue on Route 32 North to Petersham and Templeton until the road ends.

Quabbin Reservoir is vast, offering forests, farmlands, and scenic views. The south edge of the reservoir provides picturesque sites close to the lake. The roads are smooth and well-maintained, though Belchertown's area is gravel and lacks clear markings. Windsor Dam is a great scenic stop, and Petersham's county store offers amenities and memorable sandwiches.

Explore These Historic Motorcycle Routes with a Motorcycle Rental from Riders Share

Experience these historic motorcycle rides near Boston with a rental from Riders Share, the best option for motorcycle rental in Massachusetts. Discover the rich history and scenic beauty of these routes with ease and convenience. Book your rental today and start your adventure!