Hillsborough comprises four villages, the most prominent of which lies along the Contoocook River and grew up around the thriving woolen and hosiery industry in the mid-1800s. The town is home to five stone arch bridges—none of which were constructed using mortar. The nation's 14th president, Franklin Pierce, was born in Hillsborough and lived here until he married.

Begin a good drive through the area by heading north up School Street from downtown Hillsborough. Continue 3 miles past Fox State Forest to reach one of the state's best-preserved historic districts, Hillsborough Center, where 18th-century houses surround a green. Continue north 6 miles through the similarly quaint village of East Washington and another 6 miles to reach the Colonial town center of Washington. This picturesque arrangement of white clapboard buildings is one of New Hampshire's highest villages. You can loop back to Hillsborough proper via Route 31 south.

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