Massachusetts is packed with covered bridges, and this road trip pulls together some of the most interesting ones into a single, unforgettable route.
You will drive through creaky wooden tunnels, cross rushing rivers, and pass bridges that have been standing strong for over a century.
Some are still open to cars, others are perfect for quiet walks, and a few come with epic stories that you wouldn’t expect.
If you love history, scenic drives, and stops that feel a little off the beaten path, this road trip is about to become one of your favorites.
1. Historic Pepperell Covered Bridge
The Historic Pepperell Covered Bridge is located on Groton Street in Pepperell, stretching 95 feet across the Nashua River.
It was originally built in 1845 but has since been rebuilt several times with the most recent being in 2010.
Today, it uses a modern timber design inspired by the classic Town lattice truss, which you can spot by its crisscrossed wooden beams inside.
The bridge features natural wood, is covered from end to end, and open to both vehicles and pedestrians, with walkways for those on foot.
It is a perfect spot for slow strolls, photos, and river views.
2. Historic Arthur A. Smith Covered Bridge
The Historic Arthur A. Smith Covered Bridge is located in the tiny hilltown of Colrain in western Massachusetts, crossing the North River along Lyonsville Road.
Originally built in 1868, this bridge spans over 100 feet and uses a Burr arch truss design, which mixes curved wooden arches with straight beams to keep it strong and sturdy.
This covered bridge is one of the only ones that is still open to cars, so you get the classic one lane crossing experience complete with creaky boards and tight turns.
It is painted red, surrounded by forested hills, and named after a longtime local resident, making it feel like a true backroads find as you continue your covered bridge road trip.
3. Historic Bissell Covered Bridge
The Historic Bissell Covered Bridge is located in Charlemont, in Franklin County, carrying North Heath Road (Route 8A) over Mill Brook.
Rebuilt in 2009 to replace an older bridge from 1840, this 92-foot long bridge uses a long truss design and still allows vehicles, so you drive straight through its narrow wooden tunnel.
The bridge is a historic wooden structure with weathered timber that stands out against the green riverbanks and rolling hills around it.
Because it sits right in town near homes and small businesses, this stop feels casual and everyday, like a covered bridge you might cross without even realizing how rare it is.
4. Burkeville Covered Bridge
The Burkeville Covered Bridge is located in the town of Conway in western Massachusetts, crossing the South River.
Built in 1870, this 107 foot long bridge is one of the oldest covered bridges in the state.
It has a rare design using wooden trusses with iron tension members and has survived floods, storms, and more than a century of wear.
The bridge is closed to cars and open only to walkers, which makes it a quiet spot to hear the river rushing below and check out the wooden beams up close.
Surrounded by trees and farmland, this stop feels peaceful and remote.
5. Historic Upper Sheffield Covered Bridge
The Historic Upper Sheffield Covered Bridge sits just outside downtown Sheffield in the southern Berkshires.
It is located on Covered Bridge Lane, where it spans the Housatonic River.
Rebuilt in 1999, this 93-foot bridge uses a Town lattice truss. The original bridge from the 1830s, once among the oldest in Massachusetts, was destroyed by fire in 1994.
It is open only to pedestrians today, with posts blocking vehicles, so you walk through its long wooden interior while river views and open farmland stretch out on both sides.
Because of its age, historical significance, and scenic river location, this bridge stands out as a memorable stop on your covered bridges road trip.
6. Ware-Hardwick Covered Bridge
The Ware-Hardwick Covered Bridge, also called the Gilbertville Covered Bridge, is located in the village of Gilbertville within Hardwick, crossing the Ware River.
Built in 1886, this approximately 137-foot long bridge uses a Town lattice truss that has kept it standing for over a century.
It is still open to car traffic, so you drive through a narrow wooden passage with river views popping up on both sides.
7. Historic Vermont Covered Bridge
The Historic Vermont Covered Bridge is located inside Old Sturbridge Village in central Massachusetts, spanning a small stream near the back end of the museum grounds.
The bridge is an authentic covered bridge, originally built in Dummerston, Vermont, in 1870, with a wooden lattice truss and a long, gently sloped roof.
The town planned to destroy the covered bridge due to a new highway under construction but instead, in 1951, it was moved to Massachusetts.
It’s located inside Old Sturbridge Village which is a living museum that aims to show people what life was like in rural New England during the late 1700s and early 1800s.
Please note that you can only see the covered bridge if you buy a ticket to enter Old Sturbridge Village which is only open on Fridays, Saturdays and Sundays.
The bridge is only open to foot traffic, so you can walk straight through and look out at the river, nearby farmland, and costumed interpreters going about their daily chores.
Because it sits inside a living history museum, this stop feels like stepping into a 19th century postcard, making it a fun and unexpected twist on your covered bridges road trip.
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