After attending the Friends Select School for his early education, Longstreth entered the Westtown Boarding School in 1899 at the age of 13. The school had a long, distinguished history having been first established in 1799 by the Members of the Philadelphia Yearly Meeting of the Religious Society of Friends (Quakers). The school campus, located in Chester County, Pennsylvania, is still located on the same 600 acres as when it was originally founded. It is one of the oldest boarding schools in the United States.

During his time at Westtown from 1899 to 1904, Longstreth was active in the school community. The school publication notes his 1901 concert recitation of the poem “Evening Star” by Edgar Allen Poe; his 1903 entry into the school elocutionary contest; and his 1904 entry into the school elocutionary contest with a reading of “The Chambered Nautilus” by Oliver Wendell Holmes. Longstreth “played tennis and football, skated, bobsledded, and went on solitary hikes.”[1] It was at Westtown that Longstreth would discover the writings of Henry Thoreau, which would have a significant impact on his life. Longstreth would later describe the school as “a country heaven, a square mile of orchard, farm, and lake in Chester County, Pennsylvania.”[2]

Longstreth also actively sought to build a swimming pool for the Westtown school: “Near the close of last term, a movement was made, at the suggestion of T. Morris Longstreth, to enlist the students in the work of raising money for the proposed swimming pool. Since our return to school the various class collectors have been reporting to Master William and the total amount from this source has reached about $450. While this is not quite what we aimed to do, it brings the available funds almost to the estimated cost of the pool. Hope are entertained that the stone work may yet be done before frost, and possibly the pool be in use in the early spring. However that may be, we feel to thank the kind friends who have contributed so liberally, and hope the pool may be a success for their sakes as well as our own.”[3]

Longstreth graduated from Westtown School in 1904. Upon his graduation, The Westonian, the school newspaper, offered a brief summary for each of the students. For Longstreth it stated that “Thos. Morris Longstreth was born in 1886, and entered in the fall of 1899. Not being of a particularly athletic turn of mind, a good deal of his time has been devoted to his love of art. His mental pop-valve is very often blown off is horrible puns.”[4] Each member of the class wrote a graduating essay, which for Longstreth was titled “Distinctive American Art.” Demonstrating his appreciation of his Westtown education, in 1974 for the school’s 175^th anniversary Longstreth wrote that “Westtown lasts because it keeps heading in the right direction . . . and because the Quaker ethic that supplies its energy draws largely on immortal truth.”

Recollecting his childhood, Longstreth wrote of his fondness for family and summer vacation and his love of books: 

“As I remember it, my boyhood was pretty well divided between times, good or bad, and the timeless, which was perfect. I approved of mealtime and disapproved of bedtime. There was schooltime, an uneven adventure, my father's coming-home-from-business time, and the great stated times that cast their brightness before—the Fourth of July, Thanksgiving, Christmas. Best of all was the liberation from city school into country summer and wonderful weeks by the sea.

Father and a storytelling aunt watered my sprouting imagination, but it was through books that I installed myself in life. Henty and Hans Christian Andersen and Cooper and, above all, Dickens were my private tutors. No school teacher is as wise as a library, nor half so attractive. I gathered up myself while in company with the Count of Monte Cristo, Pickwick, the Virginian, and while tracing the route of Bunyan's hero. What school board is rich enough to provide teachers of their humane caliber? One third of my reading was new knowledge, one third wonder, and the remainder, the kindling of emulation in an air of joy.”

                              --T. Morris Longstreth. “A Paradise Regained.” Suburbia Today. November 1959.

Longstreth entered Haverford College (at Haverford, Pennsylvania, a suburb of Philadelphia) on scholarship in 1904 with a class with 42 other students. Longstreth was active in the college community, playing in the Haverford Musical Club, was a member of the class relay team, and authored numerous essays for The Haverfordian, the school publication. In December 1906 he was elected to the Haverfordian board and later served as an Associate Editor. He was active on the track and tennis teams. In the winter of 1908 Longstreth worked in England for several months as tutor for a private family. He would take four more working trips to Europe as a tutor over the next several years.

While at college Longstreth also worked at a small side business as college agents for a local shoe repair company. An advertisement in the 1907 class yearbook stated: “Fine Shoe Repairing. Take Shoes to room 43 Barclay Hall, either Monday, Wednesday or Friday, and we will have them repaired and returned the second following evening. BURTT AND LONGSTRETH. YETTERS Shoe Repair Shop, Anderson Ave., Ardmore, Pa.”[5]

Longstreth graduated from Haverford College in 1908 with a Bachelor of Arts (B.A.) degree. Haverford College was established by members of the Society of Friends, the first Quaker college in the United States.