Tolland was named in May, 1715, and incorporated in May, 1722. According to some, the town derives its name from being a toll station on the old road between Boston and New York. Alternatively, its name could have been taken after Tolland in Somerset, England. Today Interstate 84, the main highway connecting New York City, Hartford, Connecticut and Boston, bisects Tolland, but the town retains a charming village feel. Tolland Green is the informal center of the community, and a national historic district. The Green's features include an old-fashioned penny candy and antiques store known to locals as the 'Red and White'; the town's original 19th-century town hall, now an arts center; the 'Old Tolland Jail' museum; the 'Tolland Inn' bed and breakfast; and the Hicks-Stearns Museum, a restored Victorian house. The architectural styles on display, including the white steeples of several churches, are reminiscent of a picture-postcard New England scene. The town is also home to the supposedly haunted 'Benton Homestead'.

Many of the town's adults work in Hartford, located about 25 minutes away, often at one of the city's many insurance companies, or for the neighbouring University of Connecticut in Storrs to the south. A family-oriented town, the landscape of Tolland is primarily composed of large houses, and mansions on plots of around two acres. Undeveloped, forested land covers the area between the town's many residential developments. Containing two state forests and several municipal parks, the town retains a relatively rural character.

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