 Readsboro is in the southeast corner of Bennington County, bordered by the town of Monroe in Franklin County, Massachusetts, to the south, and by the towns of Whitingham and Wilmington in Windham County, Vermont, to the east.The Bennington County towns of Searsburg (north), Woodford (northwest), and Stamford (west) also border Readsboro.The main settlement in town, also named Readsboro, is located in the southeast part of the town, along the Deerfield River, a tributary of the Connecticut River.