Nestled in the valley between the first and second mountain one of the oldest parts of West Orange shows almost no evidence of it’s early history. In the section of Pleasantsdale today it is nearly impossible to imagine this area as a self sustaining farming community to which it owes it’s humble beginnings.

          According to tradition the first settler to the valley was Samuel Condit (1696-1777). In 1720 he purchased a large section of land lying between the mountains that afterwards became known as Pleasant Valley. Condit had five sons that all fought in the American Revolution at the Battle of Springfield. One son Daniel was born in 1723 at the Condit homestead that encompassed seventy acres once located at the present day corner of Pleasant Valley Way and Eagle Rock Avenue. Samuel Condit also deeded all of his sons an additional fifty acres each.

          The West Branch of the Rahway River that flows through the valley provided a source of water and fertile farming soil for the early settlers. The Vincent family were among the early farming families. According to Cathy Vincent, a direct living descendant or the original settler, her ancestor Thomas Vincent was born in England in 1791. He came to America as a British soldier in the War of 1812 and remained here after the war. He came to West Orange in 1835 and settled on the land where Degnan Park is today. The Vincent family eventually owned more than 1,000 acres of farm land in West Orange and Livingston. This even exceeded the holdings of the original settler Samuel Condit. At the Vincent farm east of Pleasant Valley Way the riverbed was widened to form the landmark that is Vincent’s Pond today. The purpose of this pond was to provide drinking water for livestock and a large dairy herd on the Vincent farm.

        Another well concealed landmark that is perhaps the most enduring reminder of Pleasantdale’s hidden history is the Pleasantdale Cemetery. It is the only cemetery in West Orange and was originally called the Pleasant Valley Burial Ground. Ambrose Condit (1794-1876) a descendant of Samuel Condit, and Henry Walker (1806-1891) became partners in the cemetery in 1834. It incorporated in 1929 and came under the control of the Pleasantdale Cemetery Association as which it remains today. There are war veterans buried there from the War of 1812, The Mexican War, Civil War, World War I & II and the Korean War. The cemetery also has many graves from the original Pleasantdale settlers including the Condit and Vincent families.

         The first school in Pleasantdale was erected in 1870 and the current Pleasantdale School, although rebuilt and renovated, still sits at the same location. By the 1870s Pleasantdale was a community with a strong German influence. Immigrant farmers and stonecutters employed at nearby Shrump’s Quarry founded the German Presbyterian Church in 1878. Today it survives as the Pleasantdale Presbyterian Church. The quarry was perhaps the oldest of several sandstone quarries that once operated in West Orange. It was on Eagle Rock Avenue west of current day Pleasantdale center. It provided the stone for St. Mark’s Church in West Orange constructed in 1828. Prehistoric fossils were uncovered in 1904 at the quarry buried 80 feet under solid rock.

       In 1908 Louis and Lena Green, purchased an old farm house on a 60 acre site in Pleasantdale. It became Green’s Hotel and at one time it was considered the largest hotel in Essex County. Nightly entertainment featured comedians such as Milton Berle, Red Buttons, and Jerry Lewis. The hotel is now The Green Hill senior nursing home. Several other small hotels such as the Idyl Hour and Klausner’s hotel also flurished for a while but were gone by the late 1930s. The Goldman Hotel was built in the late 1940s and grew into a large sprawling complex the one had a nine hole golf course. The hotel was remodeled in the 1960s and became the Town and Campus Hotel. Today this property occupies the luxurious Willshire Grand Hotel.

          Following World War II veterans housing in the form of barracks were constructed in Pleasantdale in 1946. The Vincent Family homestead that was located across the road from Degnan Park was razed to make way for 148 units. They were subsequently replaced by modern development. The quaint setting of Pleasant Valley Way so inspired the song "Pleasant Valley Sunday" written by Gerry Goffin and singer Carole King and made famous by the rock group The Monkees in 1967. What began nearly 300 years ago as a rural farm in a pleasant valley has emerged today as the diverse community of Pleasantdale with a firm footing into the 21st century.