Woodstock : Vermont


What It Is Like to Retire in Woodstock

Woodstock, Vermont, has been described as “The Prettiest Small Town in America” by Ladies Home Journal Magazine, and few could debate that.  Woodstock Village is a quintessential community that includes a town green surrounded by private homes, churches and the courthouse, with many of these properties listed on the National Register of Historic Places. The Ottauquechee River flows through the town, complete with covered bridges, and the tree lined streets with shops, art galleries, and a 125 year old general store all add to its beauty.  Woodstock Village is an incorporated village in the town of Woodstock, and has a population of approximately 900, according to the 2010 census.  But what is considered the Town of Woodstock not only includes Woodstock Village, but also the small hamlets of Taftsville, West Woodstock, South Woodstock and Prosper, which have a combined population of approximately 3,200 residents. 

The Rockefellers were instrumental in the development of Woodstock Village and how it stands today. Laurance S. and Mary French Rockefeller’s belief in conservation and sustainable land use are reflected here, as they helped preserve the 19th century architecture and had power lines buried underground. Rockerfellers also built the Woodstock Inn as central point for the town, and owned the land and mansion where the historic Billings Farm and Museum sit today.  

Woodstock is a very popular tourist destination which is important to the town’s economy, especially during the autumn months when tourists flock to New England to view the fall foliage. Aerial photo courtesy of VladislaV Tuchkov and Wikipedia in the public domain.


Where to Retire in Woodstock and Home Prices

Zillow reports the median home value to be $433,262 in late 2020.  Many of the houses are second homes to people living in cities such as New York and Boston.


What Is Special about Woodstock

Woodstock is a beautiful, historic, and scenic small town that offers outdoor recreation for all seasons. Its village green and surroundng streets make for a very walkable community with many dining choices, shops and galleries. 


What Is Not Special about Woodstock

Woodstock is a little isolated with no large city close by (Boston is 115 miles away); high cost of living; the nearest international airport is over 100 miles away away in either Hartford CT or Boston MA; winters are cold and snowy.


Who Will Like Retirement in Woodstock

Those who want a picturesque, and walkable small town with a low crime rate, would enjoy retiring in Woodstock.


Local Economy Is Driven by

The economy of Woodstock is driven by Tourism, Arts, and Recreation.


Climate and Physical Environment

Woodstock experiences all four seasons and has average January temperatures of 18 degrees, and July average temperatures of 69 degrees.  The town records an annual snowfall of about 68 inches.


Restaurants & Cultural Scene

Woodstock offers tranquil surroundings with the hills and rivers, and is a quaint town of art galleries, shops, restaurants and a historical district. Market on the Green and free concerts occur during the summer months, along with live theatre.  The town also host many festivals and events which include the Apple and Crafts Fair that takes place during the fall, and the popular Wassail parade, which is an annual winter affair.  The Billings Farm and Museum allows you to explore the operations of a dairy farm which was established in 1871 by Frederick Billings, who was known for his work as a conservationist. As a pioneer in scientific farm management, he set out to make his farm a model dairy operation.  Tripadvisor.com reviewers recommend visiting the farm and museum, along with suggesting several restaurants to try.



Woodstock has a low crime rate.

Medical Facilities

The Ottauquechee Health Center is located in Woodstock; Mt. Ascutney Hospital is in Windsor, about 15 miles away.



During the summer months, Woodstock provides free trolley rides; Amtrak is 11 miles away in White River Junction; Lebanon Muncipal Airport is 19 miles away, and the nearest International Airport is in Burlington, about 90 miles from Woodstock.


Valuable Links

Town of Woodstock

Woodstock, Vermont

Billings Farm and Museum


What people are saying about Woodstock

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