Woodstock was first chartered in 1761.

It became the shire town, or county seat, twenty-five years later in 1786. As a shire town with the county's courthouse and jail, Woodstock attracted a host of professional people and entrepreneurs. Within a short period of time, Woodstock became a commercial and manufacturing center with shops and mills that produced everything from woolen products to linseed oil.

By 1830, Woodstock was one of the largest towns in Vermont. It was during this early period that many of the beautiful buildings that you see around the Green and Elm Street were built. By the 1840s, Woodstock's population began to decrease - a trend that continued after the Civil War. With the advent of improved transportation and industrial practices, goods made in large mill towns and factories could be brought to Woodstock and sold at cheaper prices than locally-made products. This, in turn, lead to a decline in Woodstock's manufacturing industry and many people went elsewhere - such as Lowell, Massachusetts - to find work.

Interestingly, however, while improved transportation (particularly the railways) ended up negatively impacting the area's mills, it helped Woodstock reinvent itself as a tourist town. When the Woodstock Railway was completed in 1875 - connecting Woodstock to White River Junction and from there to Boston, New York, and a myriad of other towns and cities - it allowed city people who wanted to escape from dirty, congested, urban areas to board a train and arrive the same day in the small, quaint town of Woodstock, Vermont. After the railway to Woodstock was discontinued in 1933, Woodstock continued to grow as a resort town because automobiles made remote areas like Woodstock accessible.

Today many people visit the Woodstock area so that they can participate in outdoor recreational activities, enjoy the area's natural beauty, shop at local stores and galleries, and visit many historic sites such as the Woodstock History Center.

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