The story of Highfield Hall coincides with the arrival of the railroad in Falmouth on July 18, 1872. The ability to reach Cape Cod from Boston or from New York by train transformed the area from a quiet farming and fishing community to an exuberant summer community. Middle class families stayed in inns, many of them homes converted to lodgings to handle the explosion of summer visitors. Wealthier families eventually built seaside estates in areas such as Quissett, Chapoquoit and Penzance.

Among the first newcomers escaping the heat of the city were the Beebes of Boston. James Madison Beebe, wealthy from various dry goods and manufacturing businesses, and his wife, Esther E. Beebe, first converted the Thomas Swift House on Shore Street to a summer home they called Vineyard Lodge. They subsequently bought more than 700 acres of land on the hill above the railroad station, more than half of which has been preserved as Beebe Woods.

After the death of James Beebe in 1875, his children built two grand residences on the hill. Brothers Pierson and Franklin and sister Emily built a lavish “summer cottage” in the Queen Anne stick style modeled after the British Pavilion in the great 1876 Philadelphia Centennial Exposition. Highfield Hall was completed in 1878, and its sister mansion, Tanglewood, where the J. Arthur Beebes took up residence, was finished in 1879. Thus began over fifty years of Beebes living and entertaining in their “summer cottages” at Highfield. In its heyday, the hill must have been a bustling scene. The miles of carriage trails, riding trails, gardens, two huge homes, and numerous outbuildings required a small army of servants to maintain. The Beebes even started a farm on Shore Street to provide produce for their Falmouth and Boston residences.

The Beebes were undoubtedly a formidable family. The children made an impact on Falmouth with their financial support for the building of St. Barnabas Church on Main Street (1890) in memory of their parents, St. Barnabas House (1890), a carriage shed (1894) for the church which in 1962 was converted into a garden chapel, and conversion of the Bodfish House into the Rectory (1901). For some years in the 1880s, the Beebes were the largest taxpayers in Falmouth.

Franklin, the last of the Beebe children, died in 1932. After that, Highfield Hall passed through a succession of owners, each with a dream for its use. First, in the thirties, E.H. Bristol wanted to turn it into a health resort. That was succeeded by two dreams in the forties: J. Elwin Wright, a religious revivalist, wanted it to become a religious hotel and retreat. Subsequently, Arthur J. Beckhard ran the two mansions as hotels and converted the former stable into what is now Highfield Theater.

In 1949, the entire Beebe estate was purchased by DeWitt Ter Heun, a friend of Arthur Beckhard. TerHeun and his wife loved the theater and the opera and hoped to turn the Highfield estate into a center for the performing arts. They launched a training ground for student actors, inviting first Williams College and then Oberlin College to perform at Highfield Theatre. The couple remodeled Highfield Hall to serve as their summer residence, adding a plantation-style front on the building. A portion of the house was in use as a dormitory by the theater company, while all of Tanglewood was used for that purpose. Mr. TerHeun’s daughter, Patricia, converted the Tanglewood stable into an art gallery, showing the works of abstract artists such as Jackson Pollack and Robert Motherwell. The TerHeun summers were alive with theater, art, and culture on the hil

After Mr. TerHeun’s death in 1962, the estate was eventually purchased by summer residents Marjorie Whittemore and Stanley Welsh. They ran the theater and kept up the two houses while considering the options of what might be done with the property. At that time, the Highfield parcel was the largest single plot of developable land on Cape Cod. Welsh and Whittemore, who were siblings, considered creating a planned community on the property which would have featured clusters of houses, shopping, and a school (much like the concept employed a decade later at Mashpee Commons). Up to 500 residential units were considered, but various roadblocks from town officials, along with Whittemore and Welsh’s own hesitancy to develop the land, prevented any progress with the concept.

In 1972 the entire estate was purchased by Josephine and Josiah K Lilly III. The Lillys generously gave the nearly 400 acres of Beebe Woods to the town for permanent conservation as green space. The buildings and acreage on which they stood were donated to a local arts organization.

Sadly, on May 20, 1977, Tanglewood succumbed to the wrecker’s ball and bulldozers, and Highfield Hall entered two decades of neglect and vandalism.

In 1994, Highfield almost suffered the same fate as Tanglewood when a demolition permit was pulled by the owners. However, the Town of Falmouth had just instituted a demolition delay bylaw, which mandated a 90-day period after application for demolition of any historic building so that the local Historical Commission could attempt to effect a preservation compromise This bylaw went into effect two days prior to the permit being issued!. An advocacy group, Friends of Highfield, sprang into action to save the building. That group became a not-for-profit corporation, Historic Highfield, Inc., in May 1994.

Many years of legal disputes followed as Historic Highfield tried to stave off demolition and gain control of the building from its nonprofit owners. Volunteers cleared the lawn, boarded windows, and tried to ward off further decay and vandalism. They also raised money and worked to convince residents that Highfield Hall was worth saving. Eventually, collaborating with Selectmen, Historic Highfield was able to convince the town that Highfield Hall was important to the Falmouth community and extraordinary measures were warranted to save the property.

In 2000 Town Meeting Members authorized Falmouth Selectmen to take Highfield Hall and six acres by eminent domain, and in 2001 the Town signed a lease with Historic Highfield to renovate and operate Highfield Hall. The extraordinary restoration effort that followed was made possible through donations totalling in excess of $8,000,000 — almost all of which were contributed by private individuals.