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Founded in 1785, the community originally comprised five Shaker households oriented linearly along a 1.3-mile stretch of road. Each family (the North, Church, Center, Second, and South Families) had its own plot with a dwelling, workshops, and outbuildings (constructed 1785-1876), and at its height in the mid-nineteenth century, the community comprised 600 people across 6,000 acres. Much of the district remains privately owned, but a trail system guides visitors through the landscape and to select historic buildings.

Shaker Road serves as the main axis, running southeast from the town of New Lebanon to converge with Darrow Road. Along this central spine are significant historic buildings (e.g. the Great Stone Barn, 1860; the First Meetinghouse, 1785; and the North Family Workshop, 1825), executed in the Shaker style and characterized by functionalism, simple lines, and modest materials. Less than a mile from the Massachusetts border, the undulating landscape is characterized by paved, single lane roads bordered by lawns, irregular plantings of deciduous and coniferous trees, and occasional fencing, often without curbs or sidewalks. Columbia Pike (U.S. Route 20) constitutes the eastern limit and borders a forested, minimally developed section of the district.

In the eighteenth century Shaker residents created a patchwork of crop fields, orchards, pastures, and timber lands—some of the stone walls for which are still extant—and installed waterworks such as mills and reservoirs. Less than a mile east of the district’s center is Shaker Swamp, where early residents learned from Native peoples how to cultivate at least 74 medicinal plants.

In 1930 the Lebanon (now Darrow) School, a private high school, purchased 300 acres at the south end of the district and preserves approximately 40 historic buildings. The Mount Lebanon Shaker Society was listed in the National Register of Historic Places in 1966, and it was designated a National Historic Landmark in the same year.