What to See in Great Barrington - Top Sights and Attractions

Performing arts theater in Great Barrington, Massachusetts. The Mahaiwe Block is a commercial and theater building in the heart of downtown Great Barrington, Massachusetts. In addition to smaller businesses, it houses the Mahaiwe Performing Arts Center, the town's only major performance space. It has been in virtually continuous operation since its construction in 1905. The building is located at 6-14 Castle St. and 314-322 Main St, and is listed on the National Register of Historic Places.

The building's condition and fate in the 1990s was a major contributing factor in the establishment of local preservation ordinances. The building takes its name from an earlier structure on the site, which its owner called "Mahaiwe House".^[1]

The Dwight–Henderson House is a historic house at 390 Main Street in Great Barrington, Massachusetts. It is the second oldest house in Great Barrington, built in 1759 for Joseph Dwight, a brigadier in the colonial militia, by local builder Daniel Allen. The saltbox home was originally built into a slope, and had three stories on the front and one in the rear. The house has been moved twice, but remains within 200 feet of its original site. The second move, the foundation that formed the wall for the original first floor, so it now presents only two stories in front.

The house is notable for several historical associations. In addition to General Dwight, who was also town moderator and selectman, and a county judge, the houses notable guests include British General John Burgoyne, who surrendered his army after the Battles of Saratoga in 1777, and spent several days here while en route to the Boston area as a prisoner. It is also the house where poet and newspaper editor William Cullen Bryant was married; he was a guest of the owner, Allen Henderson.

Since then, the house has seen a variety of uses. It served for a time as housing for the nearby Berkshire Motor Inn, and now houses professional offices. The house was listed on the National Register of Historic Places in 1976, and included as a contributing property to the Taconic and West Avenues Historic District in 1998.^[6]

The Taconic and West Avenues Historic District is a largely residential historic district south of the downtown area of Great Barrington, Massachusetts. The roughly 117-acre district includes 172 contributing elements, most of which are houses or related buildings. Two thirds of the buildings were built between 1890 and 1910, and most of the rest were constructed in a historically sympathetic way.

The southwestern corner of the district is the intersection of Maple and West Avenues. Its western boundary is a high wooded ridge that roughly parallels Castle Street, and follows Main Street and Maple Avenue on its eastern and southern boundaries. The housing in the district was built by Great Barrington's wealthier residents, and feature large houses built in a variety of popular styles of the period. The district features Georgian, Early Republic, and Mid 19th-Century Revival architecture. It was added to the National Register of Historic Places in 1998.

Great Barrington was settled in the 18th century, and was the first county seat of Berkshire County. It developed around a major crossing of the Housatonic River, which also provided power for industry. Early development in this district occurred primarily along Main Street, where houses such as the Dwight–Henderson House were built, and Taconic Street, a major road leading northwest toward Alford. Development in the district was modest through much of the 19th century, only becoming more organized in the 1880s, when a number of cross streets were laid out for residential development.^[7]