Woodbury was settled in 1673 as a farming community and then gave way to small factories in the mid- 19th century. Main Street and its outlying arteries are on the National Historic Register of Historic Places for settlements that date from the 17th to 20th centuries and many of the Colonial houses and structures along Main Street date from before 1830. The town center offers New England charm among its exquisite antique shops, art galleries and fine restaurants.

Outdoor activities abound from trail walking, swimming, kayaking and fishing within the town's three parks, three trout stocked rivers and 1900 acre Flanders Nature Sanctuary. Flanders Nature Center and Land Trust ensures that much of the town's open space will never be developed. The trust also runs year round activities aimed at families. Equestrian pursuits are also available at many local farms and stables. Located in the southernmost part of Litchfield County, Woodbury is in close proximity to Interstate 84 providing easy access to Hartford, New Haven and Fairfield Counties and in 90 minutes, Manhattan.