Laurel Hill is the Association's signature property. It was the site of the first meeting, and was the first property acquired by the Association. Laurel Hill is a heavily forested, oak-studded hill in the center of Stockbridge. An open glen slopes away from a rock cliff that acts as a natural sounding board. This property is listed on the National Register of Historic Places as part of the Stockbridge Main Street Historic District.
In 1834, Judge Theodore Sedgwick and the Sedgwick family purchased the Laurel Hill property in a deed from J.E. Woodbridge, to preserve it for public use to avoid the threat of development. The family was ahead of its time. At the start of the main access trail there is a boulder with the inscription: "LAUREL HILL THE GIFT OF THE SEDGWICK FAMILY 1834."
On Wednesday, August 24, 1853 the first meeting was held in the glen (see painting pictured below) and the Association was born. It was the doing of Mary Hopkins Goodrich, great-granddaughter of first missionary Jonathan Sergeant. Ever since, the glen has been the site of the Association's annual anniversary exercises—Laurel Hill Day.
In August 1878 the Laurel Hill property was conveyed to the Association by all of the heirs-at-law of Judge Theodore Sedgwick. The deed contains the following: "...and dedicated the same to the use, benefit, and pleasure of the public, intending that the same be protected and preserved forever for that purpose..."
Trails. The main trail goes from the rear of the Town Offices west parking lot up to the open glen. It continues around the back side of the hill down to Memorial Bridge at the Park Street cul-de-sac. A steep offshoot goes up to the summit.
Stone Rostrum. In 1905, a stone platform, seat, and rostrum were constructed in the glen, up against the rock cliff. They were dedicated as a memorial to Henry Dwight Sedgwick, president of the Association from 1881 to 1904. Sculptor Daniel Chester French (Lincoln Memorial) donated the design work; sculptor Augustus Lukeman (Stone Mountain in Georgia) executed the plans. On the front of the platform is a bronze tablet: "IN MEMORY OF HENRY DWIGHT SEDGWICK FOR MANY YEARS PRESIDENT OF THE LAUREL HILL ASSOCIATION BORN AT STOCKBRIDGE AUGUST 6 MDCCCXXIV  DIED AT ROME, ITALY DECEMBER 26 MCMIII  ERECTED BY HIS FRIENDS".
Butler Seat. At the summit of the hill is a large, semi-circular granite seat, facing west toward Monument Mountain. It was given in 1928 by Mrs. Prescott Hall Butler as a memorial to her husband. On the rear is carved: "IN MEMORY OF PRESCOTT HALL BUTLER MDCCCXLVIII  – MDCCCC ". Butler was a law partner with Joseph Choate and C. F. Southmayd—all three built estates in Stockbridge.
Adams Inscription. On the south side of the hill, on the trail section going from the glen to Memorial Bridge is a boulder with carved inscription: "THIS PATH IS A MEMORIAL OF LUCIUS S. ADAMS, M.D. THE BELOVED PHYSICIAN 1804-1880." Adams was president of the Association from 1855-1880. He had great influence on many of the early decisions and improvements.
Musgrave Seat. Just a short distance to the right of the rostrum is a seat cut into the rock, given by Lady Musgrave, the former Jeanie Field. On the back is carved: "ON REVIENT TOUJOURS", which translates: "We will always return". On the seat skirt is "MUSGRAVE".
Size. 8.1 acres
A hill bounded by the Town Offices on the north, Bidwell Park property on the east, Park Street residences on the south, and Elm Street businesses on the west.
Starting at the Red Lion Inn, head east on Main Street/Routes 7 & 102. Go a block and a half to the Town Offices. The access trail starts at the rear of the west parking lot.