In the mid-17th century, John Eliot, a Puritan missionary to the Indians, established "praying towns" where Native Americans took up Christianity and were expected to renounce their religious ceremonies, traditional dress, and customs. One Praying town, called Wabaquasset (Senexet, Wabiquisset), 6 miles west of the Quinebaug River in present-day Woodstock, was the largest of the three northeastern Connecticut praying towns.
In 1675, when King Philip's War broke out, some of the town's Indians, (especially in the southern part of the town) sided with the Mohegans and the English while others sided with the Indians led by Philip, rallying to arms on what is now Curtis Island in present Holland, Massachusetts and Brimfield, Massachusetts. During the war, the Praying town became deserted, and the English with their Indian allies marched through Woodstock to present day Thompson in the summer of 1676 burning any crops or stored corn they could find.
In 1682, Massachusetts bought a tract of land, which included Woodstock, from the Mohegans. A group of 13 men from Roxbury, Mass. (home of the Pastorate of Woodstock's earlier visitor, John Eliot), settled the town in 1686 and named it New Roxbury. Judge Samuel Sewall suggested the town change its name to Woodstock in 1690, and in 1749 the town became part of Connecticut.
A farming town in the 18th century, Woodstock began attracting industry after the War of 1812. "By 1820, there were 2 distilleries, 2 wheel wrights, an oil mill, fulling mill, carding machines, grist mills, saw mills, a goldsmith, and twine and cotton batting operations. Woodstock Valley was known for its shoe factories," according to the history page at the Woodstock town government Web site.
By the middle of the 19th century, industry almost ceased, and Woodstock reverted back to a rural state. The town then became a summer destination for wealthy city dwellers from around the East coast of the United States.
According to the United States Census Bureau, the town has a total area of 61.8 square miles (160.1 km²), of which 60.5 square miles (156.8 km²) is land and 1.3 square miles (3.4 km² or 2.10%) is water. It is the second-largest town in Connecticut in terms of land area (after New Milford).
There is a large farming community, with the most operating dairy farms in the state and gorgeous views from throughout the town.
Woodstock is an incredibly historic, rural, and agricultural area. It is not a commercialized area, with most of the businesses being locally run.
Woodstock has a solid selection of different camps and parks, fitting in with the rural atmosphere and beautiful scenery.
- East Woodstock Cemetery.
- North Woodstock Cemetery.
- Bradford Marcy Cemetery.
- Bungay Cemetery.
- Barlow Cemetery.
- Center Cemetery.
- Allton Cemetery.
- Hammond Cemetery.
- Swedish Cemetery.
- Indian Cemetery.
- Quasset Cemetery.
- Woodstock Hill Cemetery.
- Brunn Cemetery.
- Private Cemetery.
- Tomb Cemetery.
- Bolls Cemetery.
- Woodstock Academy, 57 Academy Road, ☎ . Founded in 1801, Woodstock Academy serves as the public high school for Woodstock, Brooklyn, Eastford, Pomfret, and Canterbury. The school has a variety of athletic programs and is known for its location in between Hartford, Providence, and Worcester.
- Woodstock Elementary School, 24 Frog Pond Road, ☎ .
- Woodstock Middle School, 147B Route 169, +1 860-963-6575
- Roseland Cottage, also known as the Pink House or the Bowen House, was a summer home built by wealthy businessman Henry C. Bowen in 1846. This is where Bowen hosted U.S. Presidents for his then-famous Independence Day celebrations at Roseland Park. Ulysses S. Grant bowled his first strike in the bowling alley located in the carriage barn. The pink colored house features "tall, angular gables, gingerbread trim, and 21 formal flower gardens outlined by dwarf boxwood hedges," according to a Hartford Courant article. Roseland is an example of Victorian Gothic Revival style, which can be seen in its pointed gables, scrolled bargeboards, many tall chimneys, and leaded glass windows in diamond shapes. The outside walls, of board and batten wood siding, have been painted 13 different colors over the past 150 years -- all shades of pink (as of the summer of 2006 the house was a coral or salmon color). The house still has the owners' original furniture and knickknacks. Roseland was designed (under Bowen's direction) by architect Joseph C. Wells. The design was influenced by the architectural design books of architectural critic Andrew Jackson Downing. Fine Homebuilding magazine named Roseland one of the 25 most important houses in America in its 2006 Fine Homebuilding Houses Annual Issue.
- Woodstock Fair, run by the Woodstock Agricultural Society (established in 1846) has been held since 1860. The current President of the Woodstock Fair is Susan Z. Hibbard. The annual fair is held after harvest every labor day weekend complete with a carnaval, farm compition and agricultural exhibit.
- Solair Recreation League. Is the oldest nudist camp in USA. Located in western woodstock, 5 minutes away from Southbridge, Massachusetts. It was founded in 1934 and offers activities such as nude swimming, nude volleyball, nude billiards, nude outdoor tennis, and nude boating to its members. The camp is family oriented and owned and operated by its members.
- Palmer Hall, 523 Route 169, ☎ . It serves as Woodstock’s historical society. Here, you can find tons of information about the town’s history. There are often events highlighting different works of art or pieces of history. Highlights include a handwritten letter by George Washington, Native American artifacts, and pre-colonial maps.
- Palmer Arboretum. Hidden behind Palmer Hall is a botanical park, which was donated by Minnie Palmer Dean in 1925. Once overflowing and unorganized, the Arboretum has undergone an extensive restoration effort and is now properly maintained.
- Quasset School, 24 Frog Pond Road, ☎ . Open mainly in July and August, the Quasset School is one of the oldest schools in the United States. Built in 1854, this school actually functions as a classroom for current elementary school students. Located near the Middle School.
- Fairvue Farms, 199 Route 171, ☎ . Fairvue is working dairy farm that is home to over 1600 cows, with 800 of them milking cows. Fairvue farms over 1600 acres of land. They offer tours seven days a week, but request calls ahead of time.
- Taylor Brooke Winery, 848 Route 171, ☎ . An incredible winery that tends to over 2000 vines to create a variety of their own wines. They offer a tasting room on Friday, Saturday, and Sunday which offers limited complimentary tasting or tasting of all of their wines for only 6$.
- Camp Nahaco, 302 Crystal Pond Road. A beautiful, 120 acre camp sitting on Crystal Pond. Nahaco offers a host of recreational activities such as swimming, fishing, hiking, and horseback riding. There are facilities for private events and summer camps for all ages.
- Roseland Park, Roseland Park Road, +1 860-963-9557. A 60+ acre park which has a golf course, basketball courts, boating, and fishing among many other things. Can be reserved for parties and weddings. As opposed to Nahaco, Roseland is mostly a day trip as swimming and camping are prohibited.
- Town Beach. A local beach on a 38.3 acre Muddy Pond, the Town Beach offers swimming, fishing, canoeing, and picnicking. It can also be rented out for parties, events, and weddings.
- The Mansion at Bald Hill, 29 Plaine Hill Road, ☎ . Very fancy, fairly small, and very pricey. One of the best places in the town for fine dining.
- Sweet Evalina’s Stand, 688 Connecticut 169, +1 860-928-4029. Serves breakfast, lunch, and dinner. Affordable, with a homey atmosphere. Also serves as a deli and sort of convenience store.
- The Inn at Woodstock, 94 Plaine Hill Road, ☎ . A very classy bed-in-breakfast which also hosts events and serves as a restaurant. Great for having private functions.
- Mrs. Bridges Pantry, 292 Route 169, ☎ . An authentic British experience, Mrs. Bridges offers lunch, tea, and dessert. There are over 200 different types of teas to buy in the store.
- Woodstock Grill and Pizza, 45 Route 171, ☎ . A standard pizza place with good service and delicious pizza.
- Sherwood’s of Woodstock, 35 Route 171, ☎ . One of the only true bars in town, and also offers mid-ranged lunch and dinner.
- Java Jive, 283 Route 169, ☎ . Specialty Coffee and Gourmet shop which has a host of different breakfast foods, coffees, and teas.