Located on the historic Cos Cob Harbor, home of Connecticut's first art colony, the Society's facilities include the National Historic Landmark Bush-Holley House (c. 1730); the Visitor Center, housed in a former village post office (c. 1805); the Hugh and Claire Vanderbilt Education Center, set in a mid-19th century barn and artists' studio; and the William E. Finch, Jr. Archives.

Bush-Holley House is the centerpiece of Bush-Holley Historic Site on Cos Cob Harbor. A unique dual interpretation provides visitors with two distinct museum experiences that portray the history of the house: the era of the Bushes, a colonial family who lived and farmed on the site from 1790 to 1825, and the Cos Cob art colony period from 1890 to 1920. Eight rooms tell a story of change over time, beginning with the turn of the 20th century and moving backward in time to the Federal era. On the outside the historic buildings, landscape and gardens are restored to c. 1900.

The society offers exhibits, educational programs, research library access, and recreational and educational events; the Bush-Holley Historic Site offers tours and occasional recreational and educational events.

The Museum serves as the primary repository for the history, art, and culture of Littleton. It consists of two living history farms (one from the 1860s and one from the 1890s), a small lake, a collections center, and a main exhibition and administration building. Interpreters work the farm sites, run the blacksmith shop, and teach in the schoolhouse, offering a "living history" perspective to the museum visitor.

The museum offers exhibits, research library access, and recreational and educational events (including living history events).

The Sanchez Adobe was constructed between 1842 and 1846 by Francisco Sanchez, owner of Rancho San Pedro and one-time alcalde of San Francisco. Sanchez was a leader of Mexican California who led volunteers against United States forces at the Battle of Santa Clara. Today, the site shows the different periods of local history. Visitors can take a walk on the grounds and see native plants—the Ohlone village of Pruristac was located on the site. They can view the location of the original Spanish farm buildings; explore the Sanchez family's adobe home; and discover what items were uncovered during archaeological digs, including items from the adobe's time as a hotel and speakeasy.

The site offers exhibits and educational programs.

The Museum features 56 historic exhibits, many in relocated structures; an award-winning hands-on oil exhibition, Black Gold: The Oil Experience; and the Lori Brock Children's Discovery Center for youth eight and under. In addition, the museum hosts temporary exhibitions and special events.

The museum offers exhibits, tours, research library access, educational programs, and educational and recreational events (including living history events).

This 1915 Georgian Revival home is filled with the original furnishings and memorabilia of the 28th President of the United States, Woodrow Wilson.

The house offers tours and educational and recreational events.

The Museum's historic building houses an object collection of over 1,600 items, including decorative arts, personal items, costumes, and memorabilia, related to James Monroe. Additionally, the on-site archives houses over 10,000 documents, and the library holds over 3,000 volumes of rare and historic books.

The museum offers exhibits, research library access, tours, and occasional recreational and educational events.

Stratford Hall, home of the Lee family and birthplace of Robert E. Lee, was built by Thomas Lee in the late 1730s. Today, it is furnished with an outstanding collection of predominantly 18th-century American and English decorative arts.

The site offers exhibits, tours, educational program, workshops, research library access, and occasional recreational and educational events (including living history events).

Winterthur, an American country estate, is the former home of Henry Francis du Pont (1880–1969), an avid antiques collector and horticulturist. In the early 20th century, H. F. du Pont and his father, Henry Algernon du Pont, designed Winterthur in the spirit of 18th- and 19th-century European country houses. Visitors to Winterthur will rediscover America's heritage through its collections of antiques and Americana and venture out over the fields and farmland to learn about the workings of a great American country estate. They can also wander through the 60-acre naturalistic Winterthur Garden, while children will wonder at the Winterthur's famous fairy-tale children's garden, Enchanted Woods, and enjoy hands-on learning in the Touch-It Room.

The site offers research library access, tours, exhibits, classes and workshops, educational programs, and recreational and educational events.

The Society's Rice County Museum of History contains a collection of objects, images, and artifacts ranging from prehistory to the present day. The exhibits are variable, as the Society rotates its collection through its display space. Behind the museum, visitors may explore the Historical Village, including the Holy Innocents Episcopal Church, the 1850s Pleasant Valley School, the 1857 Volg Log Cabin, and the Harvest and Heritage Halls. The Society also maintains and operates the Alexander Faribault House, built in the Greek Revival style in 1853 by Alexander Faribault for a cost of $4,000.00. The Faribault family lived in the house for a few years, moving later to a large brick mansion on the bluffs overlooking the Straight River. The house was used as a civic center and as a private home. Today, the Faribault House displays pieces belonging to the Faribault family and other early settlers.

The museum offers a slide show, exhibits, tours, educational programs, and research library access; the Faribault House offers tours.

The Museum advances the public understanding and appreciation of the art, history, technique, and technology of film, television, and digital media. It does so by collecting, preserving, and providing access to moving-image related artifacts; screening significant films and other moving-image works; presenting exhibitions of artifacts, artworks, and interactive experiences; and offering educational and interpretive programs to students, teachers, and the general public.

The museum offers exhibits, tours, film screenings, educational programs, and occasional recreational and educational events.