Last Updated: May 2026
We enjoyed finding all the covered bridges and historic homes in Bennington, Vermont — more than we expected from a brief stop on our way north.
We thought this house was condemned. It was oddly beautiful and would make a great haunted house. Then we saw people sitting on the front porch. Whoops.
Pine Hollow Campground
Located about 10 miles south of Bennington, Pine Hollow has a spring-fed pond stocked with trout, surrounded by tall pines. The packed gravel pads sit on grass. Pedestal power and water pressure were excellent. Cable was a little grainy but watchable. Wifi was genuinely good — 15 Mbps down, 8 Mbps up, more than enough for Netflix. Verizon was one bar or 3G at best. A pair of Canadian geese with goslings had taken up residence at the pond and visited regularly.
Our site was huge and private. Jake loved the grassy area. The campground had just opened a couple of weeks before our stay and was still cleaning up winter debris in preparation for Memorial Day weekend — the bathhouse and fountain weren’t quite running yet, but the setting was excellent.
Covered Bridges
Vermont has a remarkable number of covered bridges and hunting for them makes for a perfect afternoon. With poor Verizon signal, we resorted to old school navigation — compass and a paper map. A covered bridge is a timber truss bridge with a roof and enclosed sides. The purpose is simply to protect the wooden structure from weather: an uncovered wooden bridge had a lifespan of only 10 to 15 years; a covered one could last over a century. The ones we visited are still in active use, single lane, and painted red.
Henry Covered Bridge
The original Henry Covered Bridge was built in 1840. It uses a Town lattice truss design, patented in 1820 by Connecticut architect Ithiel Town. A succession of water-powered mills operated beside the bridge over the years — the last was a grist mill run in the 1920s by Bertine Henry, a descendant of the Irish-born William Henry who originally settled the land. The bridge was most recently rebuilt in 1989 by the State of Vermont.
Paper Mill Village Bridge
A natural waterfall runs beneath this bridge. Dams were built in 1784 and 1889 to harness the water power for various industries, including a paper mill that operated until about 1958. This may have been one of Vermont’s first paper mills — and possibly the source of the paper used to write Vermont’s constitution in 1791. At the time of our visit, work was underway to convert the dam to a small hydroelectric plant capable of generating enough electricity for 240 homes.
Silk Covered Bridge
Built in 1840, the Silk Bridge is an 88-foot Town lattice truss spanning the Walloomsac River in West Bennington. One of the more picturesque of the day.
West Arlington Bridge
Dating to 1852 and spanning the Battenkill River, the West Arlington Bridge is one of Vermont’s most photographed and painted covered bridges. It sits near the former home of illustrator Norman Rockwell, who lived in Arlington from 1939 to 1953 and used many of his neighbors — including this bridge — as subjects.
Battle of Bennington Monument
During the American Revolutionary War, British forces advanced south from Canada toward Albany, New York, not expecting significant resistance. Cut off from their supply lines, they decided to raid the colonial supply depot at Bennington. The Battle of Bennington took place on August 16, 1777. After two hours of fighting the British retreated, and with reinforcements arriving from New Hampshire, they were pushed all the way back to Canada. The monument was completed in 1891 to mark the centennial of Vermont’s statehood. It stands 306 feet tall — constructed of Sandy Hill dolomite, a blue-gray magnesian limestone from New York.
The views from the observation deck were incredible. There are 417 stairs — or a small elevator installed in 1956 if you prefer.
Downtown Bennington
A beautiful town with well-maintained older homes and a handful of outlet stores. We only stopped at Orvis — we simply don’t have room in the RV for more clothes. The Jeep needed gas and the service station was full service. We hadn’t seen that in quite a while.
Old First Church
The church grounds are beautiful, with a large cemetery containing graves dating back to the 1700s. Robert Frost, one of America’s most celebrated poets, is buried here. He is quoted: “In three words I can sum up everything I’ve learned about life: it goes on.”
The Tap House
A nice local brewery that also serves lunch. We enjoyed their IPA — a good stop after a morning of bridge-hunting.
Honora Winery
Honora Winery is located in Jacksonville, Vermont — about 40 minutes from Bennington. They serve both wine and beer and offer cheese plates. Their grapes are sourced from California and shipped by refrigerated truck, arriving in just three days. The wines are full-bodied, a little soft on the palate, low tannin, and easy to drink without food. We tasted their reds and bought both the Syrah and Petite Sirah.
Spring in Vermont
It was still early spring. Lilacs and wildflowers were blooming everywhere — a perfect backdrop for the covered bridge hunt.
Bennington Fish Hatchery
We drove past this every day heading into Bennington, and the sign said the public was welcome — so we stopped. There are tanks full of trout at every stage of development. The hatchery may be the largest producer of state-stocked fish for Vermont. A very small percentage of what they release is for restoration purposes; most are stocked specifically for recreational fishing. The “yearling” fish are actually 18 to 22 months old and about 10 inches long by the time they leave. Eggs arrive from the Salisbury Fish Culture Station. The trout are enthusiastic about feeding time.
Visitor Information
Battle of Bennington Monument is in Old Bennington, VT and charges a small admission for the elevator; the grounds are free to walk. Old First Church and the adjacent Old Burying Ground are free and open to the public — Robert Frost’s grave is clearly marked near the back. Bennington Fish Hatchery is free and welcomes visitors during operating hours. Honora Winery is in Jacksonville, VT about 40 minutes from town — worth the drive if you want a tasting with a Vermont backdrop. Pine Hollow Campground is in Woodford, VT, about 10 miles south of Bennington — a quiet, wooded setting with good wifi.
Practical Tips
Vermont’s covered bridges are scattered across a wide area — download a covered bridge map before you lose cell service, or pick one up at the visitor center. Budget a half day to visit four or five bridges without feeling rushed. The Battle of Bennington Monument is an underrated stop — the views from the top genuinely rival more famous New England overlooks and the crowds are minimal. The Bennington Fish Hatchery is a perfect spontaneous stop and kids love it. Spring visits from mid-May through early June bring lilac blooms throughout the region that are worth planning around.
