Western Railroad Stone Arch Bridges and Chester Factory Village Depot

The Middlefield–Becket Stone Arch Railroad Bridge District is a historic district extending through parts of the towns of Chester, Middlefield, and Becket, Massachusetts. The district encompasses a 3.7-mile (6.0 km) stretch of railroad right of way in which there are ten bridge crossings, including nine over the west branch of the Westfield River. The bridges were built in four time periods: 1840, 1866, 1912, and 1928. Nine of the ten bridges are stone or concrete masonry work, and one is a truss girder bridge. All are, with only minor exceptions, in excellent and original condition. The bridges were built to carry the Western Railroad through on its run from the Connecticut River to the Hudson River. This section of railroad was the most expensive the company had to build, costing over $1 million in 1840. The 1840 bridges were designed by George Washington Whistler, and constructed by the firm of Alexander Birney. Of the original nine stone bridges built, only three survive, all of which are now out of service. Some of the bridges were either demolished or encased in concrete during work performed in 1912 and 1927, and one bridge was demolished in 1927. One of the listed bridges (#4) was built of concrete in 1912, adjacent to one of the 1840 stone bridges (#3) that was taken out of service. The one steel truss bridge was built in 1912 by the Pennsylvania Steel Company. The district was added to the National Register of Historic Places in 1980. A hiking trail providing viewing points to the lower seven bridges was opened in 2004. All of the bridges are viewable via whitewater-appropriate watercraft from the river.

The Chester Factory Village Historic District is a historic district encompassing the historic village of Chester Factories in Chester, Massachusetts. Chester was settled in the 1760s, and the factory village was a location where water power was harnessed at an early time for grist mills and sawmills. The village got its name from the Chester Glass Factory, which operated in the area through the War of 1812. It benefited from the construction of a turnpike (now United States Route 20) leading to Chester Center in 1804, and was transformed by the arrival of the railroad around 1840. The village became an important provisioning stop for trains, and the village further benefited by the fact that the railroad bypassed Chester Center. The economic and civic life of the town gradually shifted, and Chester Factories is where the town hall and library were built. It was added to the National Register of Historic Places in 1989. The district is roughly bounded by Middlefield Road, River, Main, and Maple Streets, US 20, and Williams Street. The southern boundary is roughly US 20, with the tracks formerly of the Western Railroad the boundary to the northeast. There are some older houses in the area along US 20, while more intensive industrial development took place along the Westfield River branch which runs between the two transportation routes. The village's greatest period of growth was between 1879 and 1915, when the production of abrasive materials, and granite quarrying and cutting operations became major industries. The Fay's Clothing Store, built in 1896, is at three stories the village's tallest building.

Chester is a town in Hampden County, Massachusetts, United States, situated in Western Massachusetts. It is part of the Springfield metropolitan statistical area. The town includes the Chester Factory Village Historic District. The total population was 1,228 in the 2020 census.

Chester is a census-designated place that comprises the populated center of the town of Chester in Hampden County, Massachusetts, United States. The population of the CDP was 627 at the 2010 census, out of 1,337 in the entire town of Chester. It is part of the Springfield, Massachusetts Metropolitan Statistical Area.

Walker Brook is a brook in Hampden County, Massachusetts, in the United States. The brook collects runoff from the Berkshires and empties into the West Branch of the Westfield River in the town of Chester. The brook runs through a couple of campgrounds such as Walker Island Campground and Bonny Rigg Campground.

Middlefield is a town in Hampshire County, Massachusetts, United States. The population was 385 at the 2020 census. It is part of the Springfield, Massachusetts Metropolitan Statistical Area.

The Middlefield Center Historic District encompasses the historic village center of Middlefield, Massachusetts. It is centered on the junction of Skyline Trail, the main north-south road, with Bell and Town Hill Roads. The district was listed on the National Register of Historic Places in 2012.

Glendale Falls is a waterfall and the name of an open space preserve in Middlefield, Massachusetts owned and managed by the Trustees of Reservations. The falls, fed by the waters of Glendale Brook are one of the longest waterfall runs in Massachusetts. Adjacent to the falls on the north side lies the stone foundation of an 18th-century grist mill operated by the long-defunct Glendale Farm. The farm was established in the early 1770s by a future Revolutionary War veteran named John Rhoads. The initial success of the farm led to the construction of what is now Clark Wright Road, the sole means of accessing the falls by car. The farm was not successful for long, however; by 1799 the property was sold and Rhoads was gone. The preserve was established in 1964.

The Chester train wreck occurred on August 31, 1893, outside of Chester, Massachusetts. A bridge collapse plunged four train cars into the Westfield River, killing 14 people. An investigation by the Massachusetts Railroad Commission found that the bridge had been weakened by a maintenance crew that had removed rivets from the bridge.

The North Chester Historic District is a historic district encompassing the rural village center of North Chester in the town of Chester, Massachusetts. One of the rural community's early settlement nodes, it thrived into the early 19th century around a stagecoach tavern, a few small mills, and farming, and retains buildings and archaeological remains representative of this history. The district was listed on the National Register of Historic Places in 1998.

The Chester Center Historic District is a historic district encompassing the historic center of Chester, Massachusetts. The area was first laid out by Chester's first settlers in 1763. It remained the center of commerce and civic life in the rural agricultural community until railroads were built in other areas of the town in the 1840s. The village center declined in importance as economic activity moved to areas more readily accessible to the railroad, and the town hall was eventually moved to Chester Factories. The district includes properties on Skyline Trail near the intersection of Bromley and Lyman Roads, and features Greek Revival, colonial, and Federal architecture. It was listed on the National Register of Historic Places in 1988.

The Clark–Eames House is a historic house located at 230 Middlefield Road in Washington, Massachusetts. Probably built around 1790, it is one of the town's few surviving 18th-century houses. It was listed on the National Register of Historic Places in 1986.