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The South Shire Inn derives its name from Bennington County's unique status of being the only one of Vermont's 14 counties to have two shire towns, or County Seats of government, called half-shires. The term "North Shire" is used to refer to towns north of Arlington with Manchester as its County Seat, and "South Shire" for those towns in the southern part of the county with Bennington as its Seat. The half-shire designation was given to Manchester and Bennington in 1781 by the Legislature to please supporters from each area. To this day, the County Superior Court holds its summer sessions in Manchester and its winter session in Bennington, the South Shire.

The South Shire Bed & Breakfast is located only minutes away from Bennington College, Southern Vermont College and Williams College in Williamstown, Massachusetts. Three miles south of the Bennington Hampton Inn and ten miles north of Williamstown Ma.

Travel via Amtrak to Albany - Rensselaer Station form New York or Washington. Take the Yankee Trail bus and arrive just two blocks from the South Shire Inn. You can walk to many of the attractions here in Bennington or take a cab.