Waveny Mansion, on South Avenue, was built in 1912 by Lewis H. Lapham on what had been Prospect Farm, an early summer estate. In 1967, the town acquired the “castle” and 300 acres of surrounding parkland.

The Little Red Schoolhouse on Carter Street was built in 1865. It was in use for kindergarten through fifth grade until 1957 and  was the last one-room school in use in Connecticut. Through the years, it was maintained by The Friends of the Little Red Schoolhouse. It is now a permanent exhibit and program space for the New Canaan Historical Society. It will be opened on special occasions.

The sculptor John Rogers’ studio, a National Historic Landmark, and the 1799 Rock School House are on the grounds of the New Canaan Historical Society.

The Philip Johnson Glass House, also an historical landmark, is on 47-acres off Ponus Ridge and is available for tours.

The Gores Pavillion in Irwin Park, known as one of “The Moderns” was built in 1959.

The New Canaan Railroad Station, built in 1868, is one of the earliest surviving stations in Connecticut. Its Gothic Revival- style architecture is not usually seen in train station design in the state.