Hopkinton

This weathered wooden marvel spans the Contoocook River and holds the distinction of being the world's oldest surviving covered railroad bridge, built in 1889. The Town lattice construction creaks and echoes as you walk through, and the bridge's historic significance is matched by its practical beauty—still standing after floods, hurricanes, and decades of use. You can explore both inside the bridge and the adjacent depot museum that brings the railroad era to life.

This peaceful burial ground dates back to the 1700s and sits beneath towering trees near the 1806 stone church. The flat terrain makes it easy to wander among weathered headstones that tell the stories of early settlers, including Civil War veterans. Thanks to an Eagle Scout project, every gravestone has been mapped and photographed, making it a fascinating window into the town's founding families.

Hidden in West Hopkinton, this 153-foot Long truss bridge built in 1853 crosses the Contoocook River in a picturesque setting. The unpainted wooden sides and single-lane passage give it an authentic, unpolished charm that more tourist-focused bridges lack. It's the third bridge at this location and incorporates unique Burr arches in its design, making it a favorite among covered bridge enthusiasts.

This Georgian hip-roofed building from 1791 once hosted New Hampshire legislators when Hopkinton was vying to become the state capital. Now a private home, it's the sole survivor of three taverns that once served lawmakers and is listed on the National Register of Historic Places. You can admire its classic architecture from Main Street, imagining the political discussions that once took place within its walls.