Hillsdale Hamlet Historic District

Hillsdale is a town in Columbia County, New York, near Hudson, New York and Great Barrington, Massachusetts. State routes 22 and 23 intersect near the town center, which is listed on the National Register of Historic Places. The town has several restaurants and a general store, among other businesses. Hillsdale is known for its hilly landscape and is near Bash Bish Falls, Taconic State Park, and the Catamount Ski Area. The Harlem Valley Rail Trail, a 26-mile bike path in two sections, is located not far from the intersection of routes 22 and 23.

Dr. Joseph P. Dorr House is a historic home located at Hillsdale in Columbia County, New York. It was built in the early 19th century and is a red brick dwelling with a 2-story main block and 1+1⁄2-story kitchen ell. It features a fully pedimented gable with an elliptically shaped fanlight.It was added to the National Register of Historic Places in 2007.

The Hillsdale station was a former New York Central Railroad Harlem Division station that served the residents of Hillsdale, New York.

Pine View Farm is a historic home located at Hillsdale in Columbia County, New York. It was built in 1845 and is a 1+1⁄2-story rectangular frame dwelling with a moderately pitched gable roof. The interior features elements of Greek Revival–style details. Also on the property is a former carriage house.It was added to the National Register of Historic Places in 2002.

Catamount Ski Area is a ski resort located on Mount Fray of the Taconic Mountains in Hillsdale, New York and South Egremont, Massachusetts. Catamount is one of three ski areas in the southern Berkshires; the others are Butternut in Great Barrington, and Otis Ridge in Otis. It is one of the few remaining family-owned ski areas in New England. In addition, Catamount is home to one of the largest youth ski race programs in the Northeast.

Mount Fray, 1,893 feet (577 m), also known as Catamount because of the Catamount Ski Area located on its north slope, is a prominent peak of the south Taconic Mountains, located in southwest Massachusetts and adjacent New York. The summit is open and covered in scrub oak; it offers views west over the Hudson River Valley. The sides of the mountain are wooded with northern hardwood tree species. The 15.7 mi (25.3 km) South Taconic Trail passes over the summit of Mount Fray.

The Craryville station was a former New York Central Railroad station that served the residents of Copake, New York. It is currently located along New York State Route 23 in the hamlet of Craryville.

North Hillsdale Methodist Church, also known as North Hillsdale United Methodist Church and Wesleyan Chapel of North Hillsdale, is a historic Methodist church located at North Hillsdale in Columbia County, New York. It was built between 1837 and 1838, and is a one-story, timber-frame building in the Greek Revival style. A steeple and monumental portico were added in 1859, and a mixed use addition was built on the rear in 1959. The portico features four Doric order columns.It was listed on the National Register of Historic Places in 2010.

The Copake Falls station was a former New York Central Railroad station that served the residents of Copake, New York.

Taconic State Park is located in Columbia and Dutchess County, New York abutting Massachusetts and Connecticut within the Taconic Mountains. The state park is located off New York State Route 344 south of Interstate 90 and 110 miles (180 km) north of New York City. It features camping, hiking, bicycling, hunting, cross county skiing and other recreational opportunities.

Church of St. John in the Wilderness is a historic Episcopal church in Copake Falls, Columbia County, New York. The church, its furnishing, and the parsonage were designed by noted ecclesiastical architect Richard Upjohn (1802–1878). It was built in 1851 and is a one-story wood-frame building clad with board and batten siding in the Gothic Revival style. It features an open frame bell cote topped by a steep gable roof. Also on the property are a contributing parsonage (1853) and two cemeteries. Worship is progressive Christian, following the Book of Common Prayer and The Hymnal 1982. Sunday School is provided for the children and a choir sings at the principal service. Under the leadership of the Rev. John Thompson, The Church of St. John in the Wilderness has become a cultural center for Copake Falls, hosting stage plays, chamber music (Winds in the Wilderness), and Jazz Vespers. Each year, the church sponsors the Country Fair and Auction in July, Harvest Fest in October, and participates in Copake Falls Day in August. It was listed on the National Register of Historic Places in 1995. It is located within the Copake Iron Works Historic District, established in 2007.

Copake Falls Methodist Episcopal Church, also known as the Copake Iron Works Methodist Church, is a historic Methodist Episcopal church located at Copake Falls, Columbia County, New York. It was built in 1891–1892, and is a one-story, Gothic Revival style light frame church sheathed in novelty siding. It has a steep gable roof topped by a belfry and a projecting front vestibule. The building housed a church until 1955. It houses the Roeliff Jansen Historical Society.: 4 It was added to the National Register of Historic Places in 2012.