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A glance up Prospect St and into the past

From The Blog Woodstock: A visual history tour

Woodstock owes its charm to its history

Follow the tree-lined sidewalks down Central and Elm Streetspast the intricate brickwork of Whitcomb’s Block (1894), the Mansard roof atop Fairbanks Block (1873), and the grand 54-paned window of Unicornto the pink sandstone facade of Norman Williams Public Library for a hint of what once was.

And while the landscape of homes and shops you see today has a history dating back hundreds of years or more, older structures once stood there before them. Let's not forget those lost landmarks.

That’s why in this guide, we’re sharing a glimpse into our town’s past to understand what has changed and what remains much the same.

Historic photos and insights courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.

First settled in 1768 but not incorporated till 1837, the village was designed with its natural landmarks in mind: the stretch of brick and wood storefronts settled in the valley between Mount Tom and Mount Peg, the village green at its heart within the fertile contours of the Ottauquechee River and the Kedron Brook.

Woodstock History Center Mt Tom view
Photo courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.
Looking south from Mt Tom at Mountain Ave and beyond
Mt Tom view of town in spring
Trees and houses abound in the village of Wodstock today

Thanks in no small part to that fertile soil, Woodstock became the seat of a flourishing country trade nearly two centuries ago.

The agricultural productions are large and valuable: they consist of beef, pork, butter, cheese, apples, cider and wool, of which 9,000 fleeces were shorn in 1837

Hayward's New England Gazetteer of 1839

Several decades later, Billings Farm got its start. Previously owned and farmed by the family of America's first environmentalist, George Perkins Marsh, the farm expanded to more than 1,000 acres under the Billings name. And while the acreage has reduced to over 200 today, the outbuildings (see images below), the historic 1890 farmhouse, and many of the practices remain the same on this working farm and museum.

Woodstock History Center Billings Farm photo circa 1900
Photo courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.
Billings Farm circa 1900
Woodstock History Center Billings Farm photo present day
Photo courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.
Not much has changed at the farm over the past century...
Oxen and children 1901 at Billings
Billings Farm & Museum
Two little girls in an oxcart at Billings Farm (1901)
The Woodstock History Center Photo of the Elm Street Bridge
Photo courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.
A view of Elm St you could enjoy circa 1869

Just across the street, the Marsh-Billings-Rockefeller National Historical Park offers another expertly preserved piece of Woodstock's past.

Located on what was once a major gateway to Woodstock via the Woodstock-Royalton Turnpike, this 550-acre forested plot hosts George Perkins Marsh's boyhood home, which later became the property of Frederick and Julia Billings, followed by Mary French Rockefeller and her husband Laurance Spelman Rockefeller, all for whom the park is named.

A comparison between the image on the righttaken from the edge of the grounds looking toward Elm Street around the time the property was purchased by Billings—and today's is difficult. A copse of trees now stands where a carriage road once passed.

Elm Street and Central mid to late 1870s
Photo courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.
Green space and the profile of Mt Peg are visible from this circa 1870s image of the town center

Further down Elm Street in the 1870s as pictured above, one might find glimmers of the present day at the confluence of Central Street. The Fairbanks Block (now known as French's Block, home of Dr Coburn's Tonic) was then freshly built in place of the wooden Village Hotel (1796) and still stands today—but the wide, grassy lawn, dirt road, and the nearly-bare summit of Mount Peg belie the years between then and now.

Not pictured is the Mackenzie Fountain, which was installed in the village square approximately two decades later. It served as a meeting-place for auctions, rallies, and traffic management until its removal in 1923.

Central and Elm Street end of summer
The view of Central and Elm Streets today hasn't changed much in 150 years

This high-visibility location was also a popular parade route, with marching bands, the Glidden Tours, horse races, and even baseball teams (like the Old Reliables, local team pictured here on their way to the Windsor County Fair Grounds in 1892) drawing eager crowds to the sidewalks.

Woodstock History Center Elm Street circa 1892
Photo courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.
Woodstock baseball team, the Old Reliables drive up Elm St circa 1892
Elm Street end of summer
Horse-drawn carriages have made way for cars on Elm Street
Woodstock History Center photo E.K. Wrights Drugstore now Woodstock Pharmacy 1916
Photo courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.
Step right up to the counter of E.K. Wright's Drugstore circa 1916, now The Woodstock Pharmacy

The modification of the village's downtown structures and facades paled in comparison to the transformations seen within the shops themselves.

While FH Gillingham's has been a mainstay of Elm Street since 1886, other village pillars like The Yankee Bookshop, established in 1925, have called various downtown storefronts home. And 1916, a visit to EK Wright's Pharmacy—now Woodstock Pharmacy—meant you'd pass by penny candy and the counter of a soda fountain that almost demanded you take a seat!

Many others have come and gone in Woodstock's history, including Houghton's Red & White, which opened its doors on Whitcomb's Block in the 1960s before the Yankee Bookshop took its place.

Even Woodstock's green spaces have not been averse to change.

Thanks to the efforts of Frederick Billings, the hillsides of Mount Tom that were nearly bare of trees in 1869 due to massive deforestation are now dense with Eastern white pine, Scotch pine, Red pine, European larch, and Norway spruce.

The village green (previously known as the park), on the other hand, is awash in sunlight today due to Dutch Elm Disease which likely claimed the towering trees that had encircled the area—which once included a bandstand and seasonal ice skating rink—in foliage.

Woodstock History Center photo of the Village Green
Photo courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.
The lush splendor of the Woodstock Village Green
A present day view from the green
A present day view from the green
Woodstock History Center photo of Woodstock Inn transportation
Photo courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.
Transportation around the green from the Woodstock Inn sure has changed!
The village green in summer
Looking southwest down the green

One of Woodstock's most photographed landmarks, the Middle Covered Bridge, was not the village's only covered bridge, and in fact is new by Woodstock standards!

Middle Covered Bridge circa 1910
Photo courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.
Crowds gather in celebration on Middle Bridge
Middle Covered Bridge from the History Center end of summer
The Middle Covered Bridge today photographed from the Woodstock History Center's back lawn

A whopping seven unique bridges spanned the current site of the Middle Covered Bridge according to research by the Woodstock History Center.

The sixth was a modern iron bridge pictured here during a celebration possibly welcoming electricity to the village circa 1910. It was replaced in 1969 with the peg-framed structure you know and love today.

Woodstock Town Hall and the home of Pentangle Arts, which predates the Middle Covered Bridge by nearly 70 years, was constructed during the building boom of the 1890s and completed in 1900 as the town's opera house. Although Rutland architect Arthure H. Smith had initially erected "a plain, substantial building of modern appearance," after a devastating fire in 1927, the structure was restored in the Classic Revival style complete with portico.

Fun fact from the Woodstock History Center: The Opera House officially opened October 12, 1900 with a production of Denman Thompson’s “The Sunshine of Paradise Alley” on the stage in the new second floor auditorium.

Construction of the Woodstock Town Hall
Photo courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.
The iconic Woodstock Town Hall, under construction circa 1899
Town Hall Theatre today end of summer
Town Hall Theatre as we know and love it today

We're nearing the end of this history lesson, but don't think we forgot about Woodstock village's other covered bridge!

Woodstock History Center Marble Bridge
Photo courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.
The Marble Bridge once joined the banks of the Ottauquechee on Woodstock's west end
Woodstock History Center photo of Chrysler Garage, 1925
Photo courtesy of Woodstock History Center. © Woodstock History Center. Please do not replicate without permission.
Before its demolition, The Chrysler Garage, pictured here in 1925, stood in front of The Little Theater

The Marble Bridge, photographed above, and the Chrysler Garage shown to the right, were constructed nearly a century apart but demolished within four years of each other in the 1940s to make way for modern conveniences.

Like so many other gems of Woodstock's past, the low, sturdy stone structure of the Little Theater, which remains in that location near the Rec Center on the west side of Woodstock, outlasted them all.

Where the Marble Bridge once stood
Where the Marble Bridge and Chrysler Garage once stood
The Little Theater in summer
The sturdy Little Theater that could
View from the bridge to West Woodstock
A view of The Little Theater as you cross the bridge today

About The Woodstock History Center:

Sharing the story of Woodstock through exhibits, lectures, workshops, outreach, publications, and programs for adults, families, and children.

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