Lake Buel

Camp Half Moon is a co-ed sleepover camp on Lake Buel in Monterey, Massachusetts. Camp Half Moon was established as a boys camp in 1922. The Mann family, originally from Lititz, Pennsylvania, currently own and operate Half Moon and purchased it from Dr. Ed Storey in 1967, who had owned and operated it for over 25 years. "Doc" Storey had been a history teacher in Pelham, New York, and many campers during the 1950s and 1960s came from Pelham and surrounding communities of southern Westchester County. For many years a large number of the boys attending Half Moon came not only from the northeastern United States but also from all across Latin America. Within just a few years after the 1959 Cuban Revolution numerous families who escaped from the Communist takeover of the island and resettled in Puerto Rico were sending their sons to Half Moon to have a broader experience with American youngsters from the mainland. The camp is now for both boys and girls.

Kutsher's Sports Academy (KSA) is a summer sleepaway camp in Monterey, Massachusetts, for children ages 7–17. It was originally "conceived and developed by Milton and Joseph Kutsher and legendary basketball coach Clair F. Bee in 1968." The land was originally the Harmony Country Club. The Kutsher family owned and operated the academy until 2005 when they sold the camp to Marc White, the longtime Executive Director. Until 2007 it was located in Monticello, New York. The camp moved to the Berkshires at the start of 2008, and is now located on Lake Buel, just outside Great Barrington, Massachusetts. The former site in Monticello is being leased by an Orthodox Jewish camp.Part of the reason for the move may be because the site was considered for a casino before the deal between the Kutsher family and the St. Regis Mohawks was cancelled in favor of another site.Campers choose from a variety of sports, tailored to their own interests, either to increase their skills in a particular sport(s) or to try a sport they have not tried before. There are also opportunities for campers to play sports on a purely recreational level. Ten of the camp’s coaches have been there for more than 20 years. In 2007, Wil Cordero spent the whole summer there as a coach and has stayed with KSA ever since; other famous athletes have come to participate in a clinic for a day. Creative and performing arts activities were available as well. Mike Gilberg, a former camper and baseball coach, took over as Director of Kutsher's Sports Academy in 2016. As seen in the Times-Herald Record on December 26, 2007, the Sullivan County site was leased to a Satmar group for five years beginning in 2008. The reputation was so stellar among athletes that Joe DiMaggio and Wilt Chamberlain trained here in the off season. Wilt Chamberlain and Kareem Abdul Jabbar (then Lew Alcindor) faced each other for the first time in the Maurice Stokes Game, which was held each summer at the KSA Field House.

Eagleton School was a residential treatment facility located in Great Barrington, Massachusetts for boys ages 9–22 who have a variety of emotional and behavioral problems. It was privately owned by Bruce Bona. It was the host of the Great Barrington Christmas party.

Ski Butternut, also known as Butternut Basin, is a ski resort in Great Barrington, Massachusetts, located on Warner Mountain in The Berkshires. Channing and Jane Murdock took control of the area in 1963, naming the area Butternut Basin after the large groves of butternut trees located in the basin of the mountain. Family friends of the Murdocks', the Kennedys visited Butternut.The mountain currently features 22 trails, ten ski lifts, two terrain parks, a tubing area, and a PSIA-affiliated ski school. Ski Butternut now features 3 quad lifts. In the off-season, the mountain hosts a number of summer concerts and festivals, including the annual Berkshires Arts Festival. The hours are Monday - Friday 9 AM - 4 PM, and 8:15 AM - 4 PM Saturdays, Sundays, and Holidays. Ski Butternut also offers tubing in the winter.

Questing is a 438-acre (177 ha) open space preserve and colonial era historic site located in New Marlborough, Massachusetts within The Berkshires. The property, acquired in 1996 by the land conservation non-profit organization The Trustees of Reservations, is named for a mythical beast from Arthurian Mythology called the Questing Beast. The reservation includes hiking trails, open meadows and hay fields, vernal pools, and streams. It is open to hiking, picnicking, cross country skiing, and hunting (in season). A trailhead is located on New Marlborough Hill Road in New Marlborough. Bikes, snowmobiles and motorized vehicles are prohibited.

Rock Ridge is a historic house at 48 Tyringham Road in Monterey, Massachusetts. Built in 1898, it is a well-preserved example of a turn-of-the-20th-century summer estate house. The Shingle style house was built in 1898 for Curtis Judd, an Illinois businessman who had grown up in the area. The house was listed on the National Register of Historic Places in 1983.

Mill River Historic District is a historic district encompassing the traditional center of government and a former industrial mill village along the Konkapot River in the village of Mill River in New Marlborough, Massachusetts. The district is roughly bounded by Main Street and River Church, Southfield, Clayton, School, and Hayes Hill Roads. It encompasses about 425 acres (172 ha), and contains mostly 19th century residential and civic buildings, as well as remnants of 19th century industrial activity.The principal defining feature of the district is its narrow setting along the Konkapot River. The significant drop of the river in the area (129 feet (39 m) over a 1.5 miles (2.4 km) stretch of the river) prompted the construction of many dams and mills, of which remnants of eight survive. The housing stock in the village was built mainly in the first half of the 19th century, during the height of industrial activity, and features simple two story wood frame housing, usually with Greek Revival styling. Some houses predate the industrial period, and a number of houses were built later in the 19th century. The village declined in importance as an industrial center after the railroad was built through town, but not near the village, and most of its industrial infrastructure was eventually abandoned.The civic buildings in the district include two Romanesque churches built in the 1860s, as well as the town hall, library, and school. A few commercial buildings from the era have also survived, including the current general store. The district was listed on the National Register of Historic Places in 1994.

Dry Hill is a 206-acre (0.83 km2) nature preserve in New Marlborough, Massachusetts and is managed by the Trustees of Reservations, who acquired the land in 2000. It includes a 1.5-mile (2.4 km) hiking trail of medium to strenuous difficulty.

Monterey is a small town in Berkshire County, Massachusetts, United States. It is part of the Pittsfield, Massachusetts Metropolitan Statistical Area. The population was 1,095 at the 2020 census.

Beartown State Forest is a publicly owned forest with recreational features located in the towns of Great Barrington, Monterey, Lee, and Tyringham, Massachusetts. The state forest's more than 10,000 acres (4,000 ha) include 198 acres (80 ha) of recreational parkland. It is managed by the Massachusetts Department of Conservation and Recreation.

New Marlborough Village is a historic district encompassing the heart of the oldest village in New Marlborough, Massachusetts. It includes properties on Massachusetts Route 57, New Marlborough, Monterey and Southfield Roads. It was the town's civic heart through the late 19th century, and retains character from that period. The district was added to the National Register of Historic Places in 1982.

New Marlborough is a town in Berkshire County, Massachusetts, United States. It is part of the Pittsfield, Massachusetts Metropolitan Statistical Area. The population was 1,528 at the 2020 census. New Marlborough consists of five villages: Clayton, Hartsville, Mill River, New Marlborough Village and Southfield.