Southbridge Municipal Airport

The William McKinstry Jr. House is a historic house at 915 W. Main Street in Southbridge, Massachusetts. It is a 2+ story building, unusual because of its distinctive monitor roof. Its construction date is unknown, but it is documented in a painting of Southbridge's Globe Village area in 1822. It appears to have been intended for housing, but the monitor roof is more typically associated with mill buildings. It is known to have been occupied by William McKinstry Jr., son of an early Southbridge settler, in 1836.The house was listed on the National Register of Historic Places in 1989.

The William McKinstry Farmhouse is a historic house at 361 Pleasant Street in Southbridge, Massachusetts. Despite significant later alteration, it is one of the oldest surviving farmhouses in Southbridge. It was built in about 1780 by William McKinstry, a British Army soldier who arrived in the area as a deserter in 1748, and is still owned by his descendants. Despite later modifications (notably the 19th century front dormer and side ell, and the application of siding), the basic 1+1⁄2-story five bay plan with twin chimneys is recognizable.The house was listed on the National Register of Historic Places in 1989.

The Cliff Cottage is a historic cottage at 187 Mill Street (at its corner with Cliff Street) in Southbridge, Massachusetts. Built before 1855, it is a distinctive combination of Greek Revival and Gothic features executed in stone. It was listed on the National Register of Historic Places in 1989.

The Building at 29–31 River Street in Southbridge, Massachusetts, is one of two once similar triple-deckers built during a housing boom related to the success of the nearby Hamilton Woolen Company. Of six such houses built in the 1910s and 1920s on River Street, only it and 25-27 River Street remain. The building was listed on the National Register of Historic Places in 1989, since when its historic integrity has been compromised.

The Building at 25–27 River Street in Southbridge, Massachusetts, is one of two similar triple-deckers built during a housing boom related to the success of the nearby Hamilton Woolen Company. The relatively plain form of these buildings is in contrast to earlier, more ornate styles that preceded their construction. The building was listed on the National Register of Historic Places in 1989.

The Dani and Soldani Cabinet Makers and Wood Workers Factory is a historic factory building at 484 Worcester Street in Southbridge, Massachusetts. Built in 1914, it is a good example of a small early-20th century factory, and is important for its association with both the locally significant optical industry, and its history of Italian immigration. The building was listed on the National Register of Historic Places in 1989.

The William E. Alden House is a historic house at 428 Hamilton Street in Southbridge, Massachusetts. Built in 1882 for a prominent local businessman, it is a fine example of a modest home with Queen Anne and Stick style decoration. It was listed on the National Register of Historic Places in 1989.

The Holy Trinity Episcopal Church, formerly the Evangelical Free Church, is a historic church building at 446 Hamilton Street in Southbridge, Massachusetts. Built in 1869 for a nominally non-denominational congregation of senior Hamilton Woolen Company employees, it has house an Episcopal congregation since 1921. The building is architecturally noted for its Romanesque and Gothic Revival features, and was listed on the National Register of Historic Places in 1989.

The Hamilton Woolen Company Historic District encompasses the well preserved "Big Mill" complex of the Hamilton Woolen Company, built in the mid 19th century. Located at the confluence of McKinstry Brook and the Quinebaug River in central Southbridge, Massachusetts, the complex consists of a cluster of mill buildings and a rare collection of 1830s brick mill worker housing units located nearby. The district was listed on the National Register of Historic Places in 1989.The site of the Hamilton Company's mill had been used as a mill site since 1750, when the first water privilege was granted to William Plimpton. In 1812 James and Perez Wolcott established a cotton mill on the site, building in 1814 what was at the time the world's largest cotton mill. The Wolcotts continued to expand their business, until a dam they built gave way, irreparably harming their business. Its remains were acquired by Boston investors, who formed the Hamilton Woolen Company in 1831. They rebuilt the dam to a higher level, and in 1836 embarked on a major expansion of the premises.Among the buildings erected in 1836 are the Big Mill, a five-story brick structure that is the dominant feature of the complex. Extensively modified in 1850, the most distinctive feature of this building is an end stairwell which is capped by a tower with a Romanesque belfry. Immediately adjacent to the mill Brick Square was established. This was a cluster of brick housing units arranged around a quadrangle. This area, now bounded by Mill Street, Canal Street, and Brick Row, includes five surviving worker houses. Built in the then-popular Greek Revival style, one of them was later adapted for company offices.In the second half of the 19th century Hamilton was the dominant employer in Stockbridge, producing primarily woolen products, especially after the American Civil War cut off cotton supplies. It remained a major presence in town, although it had been eclipsed in size by the American Optical Company, until a strike in 1934 closed its doors forever. Its complex underwent expansion in the late 19th century, but many of these buildings have not survived. The company added several buildings to the complex in 1929, most notable the dye building, which features a large segmented arch window, but is not in a prominent position of visibility in the complex.

The Alexis Boyer House is a historic house at 306 Hamilton Street in Southbridge, Massachusetts. Built in 1888, it is a good local example of Queen Anne/Stick style architecture. It was built for Alexis Boyer, a political leader in the city's sizable French Canadian community. The house was listed on the National Register of Historic Places in 1989.

Trinity Catholic Academy is a private Roman Catholic school located on the grounds of St. Mary's Church in Southbridge, Massachusetts. It is located in the Roman Catholic Diocese of Worcester.The school has an approximate enrollment of 250 students and classes range from Pre-K to the 8th grade. The student body is predominantly Catholic, but the Academy does accept students of all faiths. The school official Facebook page is:https://www.facebook.com/TCABobcats/

St. Peter's Roman Catholic Church—St. Mary's School was a historic church and school building at Hamilton and Pine Streets in Southbridge, Massachusetts. Built in 1853, it was the first Roman Catholic church located in south-central Massachusetts, and one of only two Greek Revival church buildings in the city. Later used as a school and parish hall, it was destroyed by fire in December 1999. The building was listed on the National Register of Historic Places in 1989.