 Vermont Route 315 runs east–west through the center of the town, connecting to VT 30 in East Rupert and to VT 153 in Rupert proper.The town also has the hamlets of West Rupert (on VT 153) and North Rupert (on VT 30).Many historians agree that Benning Wentworth, colonial governor of New Hampshire, gave Rupert its name, after Prince Rupert of the Rhine (1619–82).