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Chester Historical Society

Orange County, New York

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The importance of a good eduction has been part of Chester's culture since before the establishment of formal schools in the early 1800's. Click here to browse additional Chester school items in New York Heritage

Updated 2020-09-05

Commencement Programs

Maple Ave School Exhibit - 2020

Here's a early histor of Chester Schools delivered by Wicks S. Board at the Corner Stone Laying at the Oakland Avenue School as published in the May 16, 1907 issue of the Middletown Times Press.


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Comprehensive History by

Wicks S. Board.

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An Interesting Article. Worthy of Preservation by the "Academy" Alumnae.

Saturday last was the date selected for the ceremony of laying the corner stone of the new High School building. at Chester, and before the time appointed, two o'clock in the afternoon, a crowd of 600 had assembled at the new schoolhouse grounds, although the weather was very unfavorable, owing to a heavy wind blowing from the north, evidently fresh from the ice fields. The Chester Military Band was early at the grounds and discoursed music which enlivened things some what.

Following is the program of the occasion, which was commenced promptly at 2 p. m.:

Music, Chester Military Band

Invocation, Rev. J. Holmes McGuinness

Chorus by school, “There's a High School on the Hilltop"

Introductory remarks, C. W. Kerner, President Board of Education

Address, J. M. Thompson, of Albany, Conductor of Teachers' Institutes

Chorus by school, ”Scarlet and Black"

School history, Wicks S. Board

Music, band

Laying the corner stone, Prof. W. Wheatley

Band and chorus, "America"

Address, J.H. Cunningham

Address, J. D. Brownell, M. D., former principal

Closing address, Prof. F. J. Squires, of Chester High School

Chorus, Chester school yell song

Music, band

Many commendatory letters were received from former principals, teachers and scholars, who were unable to be present. F. M. Rites, of Ithaca, and Charles E. Allison, of Yonkers, expected to attend, but were obliged to send regrets.


The eloquent address by J. M. Thompson was listened to with rapt attention. After the laying of the cor \ner stone, Prof. W. A. Wheatley gave a short address appropriate to the occasion.

The next speaker, J. H. Cunningham, is the oldest principal of Chester Academy, and his address was upon the advantages of a rural training. He taught in Chester Academy in the '60's, and some of his old time scholars were in the audience.

Dr. J. D. Brownell, of Walden, who was principal of Chester High School for seven years. was the next speaker, and his hearers became so interested in his remarks that they forgot the Arctic winds. He made a rousing speech, which imparted much enthusiasm to the crowd, who then remained to hear the closing address of Prof. Frank J. Squires, which was ably delivered.

The words to the songs, "There's a High School on the Hilltop" and "The Scarlet and Black," were composed by Mrs. Squires. We did not learn the name of the composer of the Chester school yell song, but we will say although it is not a thing of beauty, it promises to be a joy forever with the scholars.

Contents of Corner Stone Box.

Following is a list of the contents of the corner stone box:

Chester Independent Republican; Warwick Advertiser; Middletown Times-Press: Orange County News; New York Tribune; history of Chester schools; package of Chester views; purse of coins dating from 1802, J. P. Bull; charred piece wood from old academy, Miss Dunning: copper cent, date 1817: one, two and five cent postage stamps, Jamestown Exposition; history St. Paul's Church; Erle Railroad time table; names of teachers and pupils enrolled in Chester public schools, years 1906-'07; course of study. Chester public schools; course of study, Chester High School; copy by-laws and list of membership Chester Lodge, K. of P.; by-laws and statistics of Walton Hose Co.: list of officers and directors Chester National Bank; list of officers and members Standard Lodge, No. 711, F. and A. M.; Chester Grange, statistical and historical; Chester Free Library, statistical and historical; list of business men of Chester and vicinity: newspaper clippings from Chester Independent Republican; sealed envelopes from J. P. Bull, C. F. Wood, Raymond Masters, William Osborne, C. W. Kerner: copy Educational Outlook, May, 1904; copy Goshen Independent Republican, 1866, containing advertisement of Chester Academy, Arthur Phinney, principal, and S. Y. Satterly, president of Board of Education: courses of studies of Union Free - School District No. 1, 1884.

Letter from former Principal William Simpson, in response to an invitation to be present at the laying of the corner stone Chester High School building: Charles W. Kerner, President Board of Education, Chester, N. Y.

Dear Sir:--Nothing in my life has given me so much of satisfaction as

the success of my pupils in the Chester schools, and to know that after thirty years I am still thought worthy of a place in their memory, and no one who participates in the ceremonies of laying the corner stone of your new building, or who will participate in its dedication, when completed, will have greater pride in it than I,

(Continued on page five.)


(Continued from page one.)

in far off California, will feel. The success of your school in the past and in the future has been due and will be due, not to any teacher, not to any principal, not to any Board of Eudcation alone, but to the sturdy manhood and womanhood of the people of Orange county, and of your community. There is an education in goodness and greatness in your hills and fields, and woods and streams. That this spirit may inspire your teachers, and compel your pupils, while it animates your Board of Education, and encourages the sacrifices so often necessary to the parents who will give education to their children, is my most sincere wish. I am hoping to be in the east in June and to see for myself the many improvements of which I hear.

Yours faithfully,


Los Angeles, Cal., April 24, 1907.

School History.

The following complete and comprehensive history of the Chester school was written by Wicks S. Board:

The earlier records having been accidentally destroyed by fire, the school history of this vicinity previous to establishing Union Free School District No. 1, in 1869, is largely "hear say." and so, meagre.

Through the courtesy of J. Hudson Board, Joseph Durland, Joseph Board, J. G. Clark and J. F. Thompson, we have obtained many of the following particulars: Prior to the year 1800 the only school building within the precincts of what is now the village of Chester was a frame two-story building, since remodeled for a dwelling, now owned by C. A. S. Roe, opposite the late residence of Dr. Edmonaton deceased on Main Street. about midway between Durland's store and the East Chester station, on the Lehigh & Hudson River Railroad. The building was very close to the highway, entrance being by two or three steps to the front door.

It was built much after the usual plan of the schoolhouses of the earlier day, with a belfry, in which hung a bell (cracked, it is said) of Spanish manufacture, though it was somewhat more pretentious in that it was a two-story building. To some extent the school maintained an academic course of study, being known as the “Academy.” Two teachers, one having the room on the first floor, and the other the room "up stairs," comprised the school faculty. Jansen Vail, Samuel Gillett and a Miss Carpenter (1852), who became the wife of Jehiel G. Clark are remembered as teachers in this school by some of our townspeople, who were then pupils. In those earlier days, the scattered population generally in the vicinity, according to convenience, attended the original schools in Sugar Loaf valley (near the home of F. W. Davis); at Oxford (near the late residence of Courtland S. Marvin, deceased); at Craigville, or at the "Banker" schoolhouse, on the farm recently owned and occupied by Isaac Banker, deceased (along side what is now the Goshen-Chester State road, on the original Abraham Banker homestead farm, in the present town of Goshen.)

These were the “litle red schoolhouses,” each with a history probably dating as far back (or earlier) as the Revolutionary War days, the “Academy" being in a primitive way a village school, the forerunner of the present graded system. About the year 1842, the educational interests of Chester, Sugar Loaf, Oxford and Craigville vicinities demanded better school facilities, and about $4,000 was raised by popular subscription to erect a building and equip a school, which, as Chester Academy, brought to Chester prestige as an educational community which we are proud of today. The new “Academy" was well equipped with academic apparatus and a fine library (totally destroyed with the building, by fire, April 3, 1906), the management was excellent, and for a quarter of a century Chester Academy was a "boarding school" of considerable note in this section of the State. maintaining a college preparatory course. Among those prepare for college here were Jacob Winslow Wood. Charles B. Roe. Joseph Board, all entering Amherst; James Whitfield Wood and Thomas Yelverton, entering Lafayette; Charles E. Allison and his brother, Howard, entering Hamilton.

The first principal of the new Academy was Stephen Bross, who had taught for a short time in the "old Academy. He was succeeded by his brother, William Bross, later Lieutenant Governor of Illinois (in 1866-’70). who subsequently established by endowment the "Bross Foundation,” to call out the best efforts of the highest talent and the ripest scholarship of the world, to illustrate from science, or any department of knowledge, and to demonstrate the truth of the Bible and the existence of God;" the investigations to be published in book form, stipulating that a copy of each book, as published, should be given to the library of Chester Academy, or to its legal successor, the first two volumes having just been received by our school authorities. The succeeding principals in line of succession, as nearly as can be ascertained. were: Rev. Phineas Robinson (1845-55); Prof. Osborne Edward Orton (1863'66), later State geologist of Ohio and president of the Ohio State University, Arthur Phinney (1866): J. H. Cunningham (1867); H. P. Robinson (1868.)

The building was a two-story frame structure (about 40x60 feet). viz: Belfry over the peak of the roof in front: wide porch across front, with four large square pillars supporting the second story, which, extending, formed the roof of the porch; hallway across the building in front; staircase at both ends of hallway to second floor. Where was a large assembly room about 40x40 feet, for school entertainments and general use as a village hall. On the first floor was a corridor lengthwise through the center, on either side of which was a school room, one side being for the boys and the opposite side for the girls.

Besides the assembly hall, on the second floor, were two rooms in the front of the building one for the laboratory and library, and the other for the use of the music teacher, the late Miss Hannah Craig.

During the administration of Edward Orton, alterations were made by removing one staircase, cutting off one end of the hallway so as to provide a laboratory on the first floor, with entrance from the west side of school room using the original laboratory room on the second floor for a primary school room; also, by removing the separating partition, enclosing the center corridor in the west side of school room, thus accounting for the interior of the building as most of our grown up people remember it.

The Academy was built by carpenters, ---- Day and George S. Banker, who also cut and scored the timber, most of which came from the McGinnis mountain, some of it being hauled to the nearest roadway by three yokes of oxen tandem, driven by our townsman, J. Hudson Board. The building was located between what was then East and West Chester, West Chester being a hamlet (one store, kept by James Durland, father of our townsman, Joseph Durland: a grist mill, a plaster mill, a saw mill, a blacksmith shop and some dwellings), built along the Otterkill creek, which, at this point, furnished good water power. East Chester, where was the old Yelverton Inn (in which, in the year 1774, Richard Wisner, of Warwick, was chosen by the people of this district to represent them in the Colonial Congress in Philadelphia) and a few business places and dwellings. There was no Erie depot section, near Greycourt (earlier known as Chesterville) until after the advent of the railroad in 1841.

The site was deeded by Charles B. Durland (by will) to the school authorities so long as used for school purposes, to revert after five years abandonment to the heirs of said testator.

Jesse Carpenter (who lived on the farm now owned by Ira H. Green), James J. Board, James Durland, Gabriel Seely, Seth Satterly, David R. Feagles and C. B. Wood served as trustees. The expense was covered by tuition paid by the pupils.

About 1842-’43, a district schoolhouse was built at West Chester, a few feet from the Otterkill creek, in the rear, near the west end of the highway bridge (spanning the Otterkill), opposite the farm residence of Samuel S. Durland, with a Miss Wells for first teacher.

Miss Sarah L. Berry, who previously had taught in the old Sugar Loaf valley school, was teacher in this school from some time about 1861 until 1869, continuing with the new Union Free School District until 1879. The West Chester schoolhouse and plot were sold to J. Hudson Board. in 1875, and the building removed. About 1841-’42, the "down-town" section of the present village of Chester began to grow, in the vicinity of the Erie Railroad, which was now in operation, and sometime between 1850 and 1860, the brick schoolhouse opposite the residence (formerly owned and occupied by William M. Rysdyk, owner of "Hambletonian, 10) of George M. Roe, president of the village of Chester, was erected for the new district, one of the original trustees being Jehiel G. Clark. Rev. Mr. Otis, who built the house now occupied by Hiram Tuthill, was the first teacher. He was succeeded by William Kerr, who resigned to enter the army. in 1861. Mr. McMonagle, B. F. Decker, Robert Geary and Abraham Wright were other teachers. The original “academy,” after the building of the “new academy” was used for district school purposes until about 1855 or "58 (a short time after the down-town" schoolhouse was built, when the brick school (sold in 1878, and since made into a dwelling and now owned by Herman Gratz). was erected in the vicinity of East Chester. Miss Maggie Curry was the last teacher in the old academy building, it being then used as a district schoolhouse, moving from there to the new brick schoolhouse; but she held the position only a short time, resigning because she did not think her self capable of managing a school where some of the pupils were men with grown beards on their faces. She was succeeded by Edward Payson Pitcher, Miss Sarah Kniffen, (later wife of Charles H. Westervelt) and John W. Slauson, of Middletown, were also teachers in the brick schoolhouse. Joseph Durland was trustee at the time of the union of districts, in 1869. The four districts-East Chester, West Chester, Chester (Erie depot section) and the “Banker" district, later forming Union Free School District No. 1. In 1869, at a meeting at which the late Robert W. Colfax presided, and Lewis Masterson was secretary, the inhabitants of the several districts mentioned voted to organize Union Free School District No. 1, and the said districts, together with Chester Academy, with its equipment and rights as a registered (Regents) Institution, were formally merged, in accordance with laws then recently enacted, into the Union Free School system.

The first recorded meeting of the new district is the election of the first board of education, viz: David R. Feagles. Joseph Durland. Cornelius B. Wood, J. Bartlett Tuthill and Charles P. Smith, M.D. The board elected D. R. Feagles, president, and Joseph Durland, clerk. The first school faculty was; Miss Hannah A. Curry (Mrs. Joseph Board), academic department; Abraham Wright, grammar department; Frank R Ferris, primary (East Chester); Sarah L. Berry, primary West Chester); Camilla S. Thompson, primary (Chester depot section.)

The first term of school in the new district began on the second Monday in January, 1870. - The first annual tax was $2,600.

William B. King was the first treasurer, succeeded by Henry Masterson (1881); Jonas D. Millspaugh (1886); Charles A. Thompson (1902); Hiram Tuthill (1904.) Charles A. Thompson was collector William D. Crist, jani tor, at a salary of $30 per school anmum.

The first supervising principal was A. H. Hart, of New York city, succeeding Miss Hannah A. Curry who resigned July 2. 1871, in the academic department, Mr. Hart was succeeded in 1871 by William Simpson, the assistant teachers being Misses Laura J. Brown, Sarah L. Berry, Camilla S. Thompson, Susan B. King (sueceeding F. R. Ferris, at East Chester.) Miss King was succeeded in March, 1872. by a Mrs. Spencer, who was succeeded in April 1872, by Miss Ruth M. Everts. In 1875 the "academy" building was remodeled so as to provide three additional school rooms, and the school buildings, at East and West Chester were abandoned. In 1877, William Simpson was succeeded by J. S. Eaton, who, in 1880, was followed by B. C. Nevius. J. D. Brownell succeeded Mr. Nerius in 1881, resigning in 1888 to study medicine. A. B. Sherwood was principal, 1888-'90: F. M. Wilson, 1890-'96; J. F. Barringer, 1896-'99; C. A. Woodworth, 1899-'00; W. A. Wheatley 1900-1904; M. L. Dann, 1904-'07.

The present faculty is: F. J. Squires, M. A., principal (high school); Miss Vila L. Breene, English (high school): Miss Clara H. Schmidt, science (high school); Miss Martha W. Davidson, eighth grade: Miss Goldie V. Sayer, seventh grade; Miss Hylah Hasbrouck, sixth grade: Miss Eva M. Davis, fifth grade; Miss Nellie Vail, fourth grade: Miss Estella M. Van Gordon, primary; Miss Camilla $. Thompson, primary: Abraham Wright, primary (Greycourt.)

"The following named persons have served on the boards of education since 1869; David R. Feagles, 1869-’79; 1882-’85; Joseph Durland. 1869-’75; Cornelius B. Wood, 1869-'75; J. B. Tuthill, 1869-’78; C. P. Smith, M. D.. 1869-'89; 1890-'93; Joseph Board, 1875-’78; 1881-'97; 1900-'03; A. B. Roe, 1874-86; Hiram Tuthill, 1878-’81; D. H. Roe, 1878-'81: J. H. Board, 1879-'90; G. F. Andrews, 1882-’83; C. W. Kerner, 1883-’90; 1891-'07; C A Thompson, 1885-'96: C. F. Wood, 1888-'03; R. P. Conklin, 1893-99; T. F Law. rence, 1896-02; R. H. Marvin, 189700; 1901-'02: H. B. Masten, M. D., 1899-'01; E. T. Jackson, 1902-’07; W. S. Board, 1902-'07; B. C. Durland, 1903-'07; C. P. Smith, M. D, 1903-’07.

The presiding officers of the boards of education have been as follows: David R. Feagles, 1869-'76; ’77; ’82; ’84 – 10 years; Charles P. Smith, M. D., 1876, ’78-’82, ’81-’88 – 9 years; Joseph Board, 1888-’97 – 9 years: Charles W. Kerner, 1897-'07 – 10 years.

Clerks: Joseph Durland, 1869-’75; Joseph Board, 1875-'78; Hiram Tuthill, 1878-'82 – 4½ years; George F. Andrews, 1883 – ½ year; C. W. Kerner, 1883-90; '91-'97 — 13 years; C. A. Thompson, 1890-’91 – 1 year; C. F. Wood, 1897-'98 – 1 year; Josiah Farmer, 1898-1900 – 2 years; A. R. Conklin, 1900-’07 – 7 years.

In the year 1875, the school building was extensively remodeled. The contract for labor was let to W. A. Vail, at $2.44 per day of 10 hours for carpenters: $2.62 per day for masons. and $1.75 per day for laborers. Cornelius Schultz received the contract for roofing at $8 per square, best charcoal tin, less five per cent, for cash. The contract for painting was awarded to W. B. Wood, at $75 for three coats of paint outside, and $68 for the inside, the district furnishing material. In 1870, $2,080 was paid James Durland for land adjoining the present old site, near West Chester, with the intention of erecting a new school building in that vicinity, a previous effort to change the site to what is now the Durland & Roe tract, at a point near the present residences of R. H. Marvin and F. L Conklin (then owned by Peter Townsend), having failed by one vote. Later the idea of a new school building was abandoned, and the land purchased in 1879 (excepting one rood and 33 rods adjoining the old school site) was sold, the portion sold being the strip of land beginning with the present residence of Frank D. Vail, and continuing to and through the property of Charles D. Courter.

The original building having been remodeled and somewhat enlarged, the school properties in West Chester and East Chester were offered for sale, the former being sold in 1875 to J. H Board, and the latter, in 1878, to Daniel Diffily for $500.

In 1901-’02, a small piece of land continuous in the rear, with the one rood, 3 rods previously retained, was purchased of Samuel S. Durland, for $75.

In 1881, the Greycourt schoolhouse was built, at a cost of $1,128, W. A. Vail, contractor, the site being purchased of T. S. Durland.

In 1884, during the administration of J. D. Brownell, the first class – Misses Jennie Doland and Mattie Durland–graduated from Union Free School District No. 1. "commencement** exercises being held in the Methodist Church. The standard for graduation was 38 Regents' counts. Since, the standard has been raised gradually to the Regents' present requirements for an academic diploma.

In 1897, an addition was built on the west side front end of the previously (1875) remodeled original building, furnishing one additional school room, a laboratory and a library room, at a cost of about $1.500.

In 1898, during the administration of John F Barringer, we received a high school charter; later, during the administration of W. A Wheatley, we were registered as an approved school." i. e. as having an approved (by the State Education Department) course of study, since which time the school has been receiving tuition from the State for the instruction of nonresident high school pupils.

The district permitted the withdrawal of a portion of the original *Banker" district, in the year 1871-’72, and, in the same year received Bernard Cullen from Blooming Grove District No. 8, and, in 1892-’93, Jesse Hunter, and, in 1897-’98, John Kane were also admitted from Blooming Grave District No. 8.

April 9, 1906, the school building herein before described, with contents. was totally destroyed by fire. Origin of fire unknown. Estimated loss, $10,614.05; insurance, $7.000. With the matter of a new school building the question of choosing a new site was agitated, and finally, by vote of the district, at a special meeting held June 28, 1906, it was decided, by 169 yeas, 123 noes, to purchase, at a cost of $1,000, a new site containing about 31 acres of land on C. B. Wood's hill, overlooking the village and surrounding country.

The argument in favor of the new site was its more central location, together with the thought that education is progress, and progress educational; and so, we have decided to locate Chester Public Schools on a chosen spot in this beautiful village of Chester, N. Y., believing that environment has much to do with individual development, and that the whole will be influential on community life.

In accordance with the appropriation voted by the district, under direction of the board of education, D. H. Canfield, architect, of Middletown, prepared plans for a building, viz: Outside measurement, 101 1-3 feet by 61 1-3 feet: eight grade rooms, each about 22 by 30: high school study hall, 28 2-3 by 31; two laboratories, each 15 by 21; two recitation rooms, each 15 by 21; a library room, 11¾, by 21½; a principal's office, 11¾ by 21½, a teachers' (ladies') room, 7½ by 10, and an assembly room about 31 by 62: sanitaries (2), each about 21 by 22, in the basement, which extend under the entire building.

Ceilings, basement, 10 feet; first and second stories, 13 feet; main corridor, 16 feet wide. The building was designed to accommodate 420 pupils–about 100, more than present enrollment.

The contrast for the construction, exclusive of heating and plumbing, was awarded to D. D. Stever, of Middletown, for $29,647. The contract, signed Oct. 24. 1906, stipulated that the building shall be completed August 15, 1907.

Craigville School class: Mr. Demerest, Edwin C. (Chamberlain?), Joesph C. (Chamberlain?), Herb Garner. Circa 1890. csh-008274
Circa 1892 unidentified local Schoolhouse. CHS-008813
1896 Commencement Chester Union School. chs-015354
Sugar Loaf School. 1897. chs-006580
Chester Alumni Dinner Program & Menu. June 20, 1902 at Murray Hall. chs-005404
Miss Helen Roes Monthly Report Card Envelope, September, 1902– June, 1903. chs-007634
Miss Helen Roes Monthly Report Card, September, 1902– June, 1903. chs-007635
Miss Helen Roes Monthly Report Card, September, 1902– June, 1903. chs-007636
1903-1904 Honor Roll chs-005516
Burning of High School Building. April 9, 1906 chs-005837
Chester High School, Oakland Avenue, a.k.a. "University Heights" under construction. July 8, 1907 chs-005955
Miss Helen Roes Monthly Report Card, 1908-9. chs-007637
St Columba School Biology Class 1913: Seated: Lillain Diffily, Helen O’Hara, Mary Farrey. Standing: Maurice O’Connell & Kathryn Orth. February 13, 1913 chs-007705
Sister Miriam’s Zoology Class and Sister M. Joschin, 1st Principal of St. Columba School; Maurice O’Connell; Sister M. Joschin; Kathryn Orth; Lillian Diffily; Helen O’Hara, sitting; Mary Farrey, sitting. February 13, 1913 csh-007706
Sister Miriam, 7th - 9th grade St. Columba School teacher. February 13, 1913 chs-007707
Chester Academy Class of 1929: 1st row left to right: Mae Miller, Charles Casey, Kay Bowman. 2nd row: Elsie Hunter, Clifton (Clifford ?) Lawrence, Leonard Baird, Pearl Murray. chs-007596
Mrs. Roe's 1st Grade 1955-'56. chs-011783
Chester High School Old Academy Ave School: 54 Pupils - 22 boys, 32 girls with 3 teachers. 1897 chs-006050
Chester School Band Concert: Richard Fumanti, Conductor; Side One CH 42161-A
El Gaucho-Ted Mesang, Toccata For Band-F. Erickson, Voo Doo-Hal Walters, Sunset Soliloquy, Troika-Hal Walters. Side Two Ch 42161-B: Folk Song Suite-Vaughan Williams, Pavane-Maurice Ravel, South Pacific-Rodgers-Hammerstein, Killarney-J. Hamilton. 33 1/3 rpm. 1962 chs-006500
The Class Of 1962 Presents: "Dr. Hudson's Secret Journal." chs-006562
Former Greycourt School, now private residence on School street. 1/27/2002. chs-001792-1
Chester Academy Burns, 1906. Thursday, April 19, 1956 chs-005533
chs-017530 Chester School Corner Stone Laying Ceremony part 1+2 1907