There’s something ridiculously fun about driving down a quiet country road and suddenly spotting a covered bridge waiting ahead.
On this New York and Vermont road trip, you’ll cross nearly 200-year-old wooden bridges and experience their narrow timber interiors on foot or behind the wheel.
You’ll also find surprising stories involving major storms, state borders, famous artists, and one seriously spooky local legend.
So grab your camera, queue up your road trip playlist, and keep reading because these historic crossings turn an ordinary drive through the Northeast into one memorable adventure.
1. Perrine’s Covered Bridge
Perrine’s Covered Bridge crosses the Wallkill River between Esopus and Rosendale in Ulster County, New York, and dates to 1835.
This 138-foot wooden bridge features a Burr arch design and is the state’s second-oldest covered bridge, giving you a glimpse into the region’s past.
Cars no longer cross here, so you can walk through it, photograph the weathered wooden siding, and check out peaceful river views from the surrounding area.
Listed on the National Register of Historic Places in 1973, it’s the kind of place where you can imagine travelers crossing the Wallkill generations ago.
2. Hyde Hall Covered Bridge
About 2 hours and 20 minutes from Perrine’s, you’ll find Hyde Hall Covered Bridge inside Glimmerglass State Park in Otsego County, New York.
Built in 1825, this 53-foot bridge crosses Shadow Brook and is considered the oldest covered bridge still standing in the state, with its original Burr arch truss intact.
When you walk through the single span, make sure to look up and admire the thick timber beams overhead and the impressive arches stretching along the interior.
If you have time, explore nearby Hyde Hall, a limestone mansion built between 1817 and 1834, or follow the 2.4-mile Sleeping Lion Trail for views of Otsego Lake.
3. Buskirk Covered Bridge
From Hyde Hall, it’s a 2-hour drive to Buskirk Covered Bridge, a red landmark spanning the Hoosic River between Rensselaer and Washington counties in New York.
It measures 165 feet long and dates back to 1857, with a Howe truss design, a single wooden span, and a pitched roof that gives it a classic country-road look.
Unlike the pedestrian-only bridges earlier, this one still carries local traffic, so you can drive through its timber-lined interior before parking nearby for photos.
Added to the National Register of Historic Places in 1978, it’s a fun final stop in New York to stretch your legs and take in the scenery before continuing into Vermont.
4. Arlington Green Covered Bridge
Cross into Vermont, and you’ll reach Arlington Green Covered Bridge, a postcard-worthy crossing over the Batten Kill on Covered Bridge Road in Arlington.
Completed in 1852, it stretches 80 feet and uses a traditional Town lattice truss, with crisscrossing wooden planks supporting its single span beneath the red exterior.
And even though it’s one of the state’s oldest surviving covered bridges, you can still drive through it and pull over nearby to check out the river and wooded banks.
As for Arlington, Norman Rockwell lived and worked here from 1939 to 1953, often using locals as models for his famous illustrations.
5. Cornish-Windsor Covered Bridge
Next up is Cornish-Windsor Covered Bridge, which takes you across the Connecticut River from Windsor, Vermont, to Cornish, New Hampshire.
The 449-foot bridge was built in 1866 with two Town lattice truss spans and remained America’s longest covered bridge open to vehicle traffic until 2008.
Drive through its long wooden interior on Bridge Street, then stop on either side to appreciate the weathered siding, river scenery, and impressive scale.
With two states packed into one short drive, this is easily one of the most memorable stops on your covered bridge road trip, so don’t rush through it.
6. Taftsville Covered Bridge
After crossing into New Hampshire, head back into Vermont to Taftsville Covered Bridge, a striking red span over the Ottauquechee River in Woodstock.
Local builder Solomon Emmons III completed the 189-foot bridge in 1836, making it one of the state’s oldest covered bridges, with two spans supported by kingpost trusses.
You can drive through its long wooden passage, then stop along the riverbank to see how the red siding stands out against the water and surrounding trees.
What you see today could have looked very different after Tropical Storm Irene badly damaged the structure in 2011, but a major restoration helped it reopen in 2013.
7. Coburn Covered Bridge
Just 1 hour and 10 minutes from Taftsville is the tiny Coburn Covered Bridge, a charming change of pace tucked along Coburn Road in East Montpelier, Vermont.
Built around 1851, this 69.5-foot crossing spans the Winooski River and features a Queenpost truss, wooden siding, and a pitched metal roof.
It’s also single-lane and still open to local traffic, so drive through slowly before finding a safe spot nearby to admire its compact frame against the broad river.
As the town’s last covered bridge from the 1800s, Coburn may be small, but it carries a unique piece of local history.
8. Gold Brook Covered Bridge
Now continue about 40 minutes toward Stowe to Gold Brook Covered Bridge, better known as Emily’s Bridge, which spans Gold Brook along Covered Bridge Road.
This historic crossing dates back to 1844 and stretches 48.5 feet, with a Howe truss design, dark wooden siding, and a low single-lane interior still open to cars.
According to local legend, the bridge is haunted by Emily, a young woman who supposedly waited here for her lover in the 1850s, only to take her own life when he never arrived.
If you’d rather skip the spooky atmosphere, visit in the morning and soak up the scenery before wrapping up your covered-bridge road trip from New York to Vermont.
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