Photos Welcome to Cheshire Sign Cheshire Scenery Silver Plate Reserved Old Church Cemetery Historic cemetery on Jenks Road. It's one of Cheshire's oldest cemeteries, near the site of the first Baptist meetinghouse in town. Reynolds Rock This is a climbers' favorite and it's located in Cheshire stands 30 feet high and sits 40 feet long. Shoe Factorty Cheshire Harbor Warp Mill Stafford Plaque Located at the Stafford Hill Memorial Stafford Grave Located at the Stafford Hill Memorial Richmond Iron Co Furnace Hill Stafford Hill This is the Stafford Hill Memorial that is set back 400 ft. off of Stafford Hill Road in Cheshire. Stafford Hill This is the Stafford Hill Memorial that is set back 400 ft. off of Stafford Hill Road in Cheshire. Stafford Hill Stafford Hill Memorial is set back 400 ft. off of Stafford Hill Road in Cheshire. Block Party This is a previous years block party. Mountain View Hall's Tavern Historic tavern at 41 North Street in Cheshire, Massachusetts. Built in 1804, for Calvin Hall, a veteran of the American Revolutionary War. Cheshire Cheese Press A gift to President Thomas Jefferson in 1802. The 1,235lb cheese was made by combining milk from every cow in town, and a cheese press to handle the cheese's size. Bennington Battle This is a 4' long by 3' bronze sculpture on a rough cut rectangular stone, made in 1932. The bas-relief depicts colonial militiamen during the Battle of Bennington. Bassett Brook Bridge This bridge was built in 1830. It is one of the oldest unaltered bridges in the state if not the oldest! Bassett Brook Bridge This bridge was built in 1830. It is one of the oldest unaltered bridges in the state if not the oldest! Dean's Lime Kiln Prospect Hill Farnums Paymaster Building Mountain View Town Hall This town hall was built in 1898, after the state mandated town records be stored in fireproof vaults Cheshire Harbor Cheshire Valley & Harbor Cheshire Massachusetts Postcard. Cheshire Motel Cheshire Motel. Cheshire Trolley Trolley in center of town.