The area now comprising Woodstock was first settled in 1797. In 1815, the Governor of Massachusetts signed a petition incorporating it as the Town of Woodstock. The village of Bryant Pond, on State Route 26 in the northern part of Woodstock, is the town's service center and largest settlement. Woodstock is the location of the last hand-cranked telephone in the United States.
Woodstock was traditionally a farming and manufacturing community. While the Stowell Wood Products and Mann’s mills have closed, logging and forestry remain important to this community. Patriots Renewables has a wind project on Spruce Mountain in the town. Lakes and iconic ledges highlight the scenery.
The 4-H School at Bryant Pond is a vibrant facility for conservation education for young people. The school has expanded from just a summer program to year-long hands-on educational opportunities, as well as the site of the Telstar High School Freshman Academy.
The town has a total area of 46.88 square miles. According to estimates for 2014, the population is 1,243, and the median age is 48.8 years. Residents 55 and older make up 39.3% of the total population; those 65 and older are 21.64% of the total.