The Quintessential New England Town - Woodstock, Vermont

Cute Downtowns

Mar 18

Sometimes called “the quintessential New England town” or “the prettiest small town in America”, Woodstock is a charming destination with year-round activities. Walking the tree-lined streets of Central and Elm Streets you get a glimpse into the town’s history through its beautiful architecture while enjoying the breathtaking beauty of the surrounding countryside and the Green Mountains. Although the village’s architecture has not changed much over the years, the tenants have, with unique shops and galleries. If you are looking for Walmart, Marshalls or Target, you will not find them here; there’s no chain stores, only locally-owned businesses.

Woodstock has three historic covered bridges, which were covered not to protect those passing through, but to preserve the bridges themselves. The Lincoln, Middle and Taftsville bridges are all passable and should be visited.

The architecture in the town is not limited to small colonial buildings which you might expect. The range of architectural styles go from Georgian and Greek-Revival to Queen Anne, with some colonials sprinkled in. Laurence and Mary Rockefeller were very involved in preserving the town and ensuring the town’s sustainability. Unfortunately, when I visited Woodstock, the Marsh-Billings-Rockefeller Mansion was closed, so I would check their website for days and hours of operation.

Here is what caught my eye. I hope you enjoy!

Do you like the images posted?
Click here to explore the shop.

The Lincoln Covered Bridge was constructed in 1877.

The one lane Lincoln Covered Bridge

Lincoln covered bridge crossing the Ottauquechee River

Interior of the Lincoln Covered Bridge showing the the utilization of Pratt truss

Another view of the Lincoln Covered Bridge built by R.W. Pitney and B.H. Pitney

Stately Federal-style brick home

Part of the town green

Store window and street signs

Quaint garden gazebo

Looking down Mountain Avenue towards Middle bridge with convenient walkway

Pictured here is the interior of Middle bridge, built in 1969. Although it is one of the youngest covered bridges, it still has the old fashioned charm.

Middle covered bridge is said to be the most photographed bridge in Woodstock.

Welcoming front porch

This is the First Congregational church built in 1890, replacing the original church built in 1807.

Cloud formation over historic homes

Benches on Mount Tom’s Faulkner Path, looking down over Woodstock

The town does not have big chain stores like Bed Bath & Beyond or CVS; you will only find small locally-owned retail stores and galleries.

Taftsville covered bridge is one of the oldest covered bridges in the country.

Home made ice cream

The Taftsville covered bridge entrance

Mountain Avenue curving towards Middle Covered Bridge

Pedestrian-friendly

Artist Adrian Tans uses the Woodstock Smiler to bring a smile to residents and visitors with his changing chalk and pastel art.

F.H. Gillingham & Sons General Store, was opened in 1886 by Frank Henry Gillingham in the heart of the town, and is still family run.

A side street home

The Woodstock Inn & Resort was established by Mary and Laurance Rockefeller.

Interior of the Inn at Woodstock

The Red Rooster restaurant at the Woodstock Inn & Resort

Georgian Colonial-style home

The Norman Williams Public Library, located on the Village Green, was built in 1883.

Old red barn in nearby Quechee

Simon Pearce Factory Store, glassblowing and pottery workshop

The Mill at Simon Pearce overlooking the Ottauquechee River waterfall and covered bridge

The waterfall at Quechee

The Quechee Gorge Bridge was originally constructed as a railway bridge in 1911, and converted to a roadway bridge in the 1930’s.

The vintage shop, Who Is Sylvia?, at 26 Central Street is an interesting building hanging over Kedron Brook.

The building at 26 Central Street hangs over Kedron Brook.

Driveway leading to side street home

Tulips & watering can

The estate once owned by Mary and Laurance Rockefeller was donated in 1992 and became the Marsh-Billing-Rockefeller National Historic Park. The name of the park honors the past owners of the property including George Perkins Marsh, Mary Montague Billings French, Laurance Rockefeller and Mary French Rockefeller.

Unfortunately, when I visited the park, the red-brick mansion was not open for tours.

The house on 40 acres was designated a National Historic Landmark and listed on the National Register of Historic Places in 1967.

One of the gardens at the March-Billings-Rockefeller Historic Park

The Belvedere Complex consists of a bowling alley, garden workshop, changing rooms and greenhouse, and was designed in the 1870’s by Detlef Lien with scroll work detail. A fallout shelter was added to the basement of the building in the 1960’s.

The pool and greenhouse at The Belvedere - The Marsh-Billings-Rockefeller State Historic Park

What you should know:

Woodstock is walkable; check out the main streets as well as the side streets.
The mansion at Marsh-Billings-Rockefeller Historic State Park has limited days / hours; check their website.
Woodstock is beautiful in any season.
It can get crowded on weekends, holidays or during area events.
Visit F.H. Gillingham & Sons for Vermont-made items in an old fashioned general store.
On the street parking is available.