Upton, Massachusetts is located Southern Massachusetts, bordered by Grafton and Northbridge on the west; Westborough on the north; Hopkinton, Milford, and Hopedale on the east; and Mendon on the southeast. Upton is 15 miles southeast of Worcester, 36 miles southwest of Boston, and 187 miles from New York City. The principal highway in State Route 140. The Massachusetts Turnpike (Interstate Route 90) passes to the north in Westborough, and Interstate Route 495, the outer belt around Boston, is easily accessible to the east at interchanges in Hopkinton and Milford. The Grafton and Upton Railroad provides freight rail service in Upton, interchanging freight with Conrail in North Grafton. Contact number for the G & U: (508) 853-2849

Upton's beginnings are different from most other towns in the Commonwealth. Instead of being taken from one town or from common land, it was put together from the outlying areas of four towns: Sutton, Hopkinton, Mendon and Uxbridge. The first meetinghouse was built within the walls of the burying ground; this location in the south part was upsetting to the Westborough farmers who moved into the northwest section in the following decades. After many years of controversy, the original meetinghouse was dismantled, and a new one was built close to the center of what is now the town common. For more than 100 years, many Upton farmers supplemented their incomes by making boots.

By 1837, William Knowlton had established a flourishing straw hat business in the west part of Upton; hatmaking supplanted bootmaking and employed many citizens until 1969. The Knowlton factory has been converted into apartments and is on the National Register of Historic Places. Upton is a small, friendly community located in southern Worcester County, primarily residential in nature, and still retaining much of its original New England flavor. Upton's Historical Society not only preserves artifacts from the past, but works actively to inform its citizens about people and places, which makes it an attractive place to put down roots. Upton is located 35 miles west of Boston and 13 miles south of Worcester, providing its residents with the best of both worlds, ie., a quiet environment in which to reside and access to major cities within 45 minutes.