1845 – 1856 (circa): Jerome B. Judkins, one of the town's oldest and most prominent residents moved from Boston and purchases many acres of the Old Caleb Swan farm. He builds a house which later serves as the parish rectory, convent, and parish center. Judkins Pond was eventually filled in to become the new Winchester High School.
1876: St. Mary's constituted as an independent parish. Rev. Cornelius O'Connor is appointed first resident pastor. Rev. O'Connor replaces the small wooden chapel with a larger structure. Rev. O'Connor and his assistant take up residence at the corner of Bridge St. and Washington.
1882: Rev. O 'Connor dies. Rev. Patrick J. Daly becomes pastor. Parish numbers 900. He enlarges the church to its current dimensions and adds a tower. The first rectory is built for Rev. Daley, formerly 57 Washington St, now # 199/ 201at the corner of Washington and Eaton St. It was used until 1903 as a rectory and sold by the Archdiocese of Boston in 1915.
1888: Rev. Daly is transferred and Rev. William M. O'Brien appointed in June. Two parcels of land were purchased including where the school now stands.
1894: Rev. Henry J. Madden is appointed pastor. Stained glass windows, an organ, and the parish library, later used as a baptistry, were installed during his pastorate.
1896-1897: The church is extensively remodel led and encased in bricks by Boston architect P.W. Ford.
1902: The Judkins parcel of land with house were sold to the Archdiocese.
1906: Rev. Madden retires and Rev. Dr. Daniel J. Keleher is appointed pastor.
1907: Lightning strikes the tower 's metal cross setting the tower on fire. The tower area was destroyed.
1908: A new bell was donated by Francis O’Hara to the new tower. It was tuned to harmonize with the other bells of the town.
1909: Rev. Keleher (glasses, picture left) is given rank of Monsignor and transferred. Rev. Nathaniel J. Merritt (second, pictured left) is assigned pastor.
1910: Parish numbers more the 9,000. The first reported Italian Feast honoring the Assumption of Mary in August slowly grew to an elaborate regional affair. A Mass began at St. Mary’s followed by a procession of the statue through the Italian section of town. Other activities included fireworks and concert on Manchester field. It grew to be a two-day event. This remains an annual tradition though smaller in scale.
1911: First annual lawn party. A start is made on the construction of a new rectory.
1912 (circa): A new rectory is built by an unknown architect for the staff who have outgrown the former Judkins house. Cardinal O’ Connell lays the cornerstone of St. Mary’s grammar school.
1914: The Judkins mansion is moved back to its current location and remodeled to serve as a convent for the Sisters of St. Joseph. A devotional chapel was added. The grammar school opened, blessed by Cardinal O’Connell, in October. It was administered by the Sisters of St. Joseph.
1922: St. Mary’s High School for Girls opens.
1929: Parishioner donates land known as “The Lower Campus”.
1931: Cardinal O’Connell establishes the Immaculate Conception parish, combining the northern part of St. Mary’s with the southern part of St. Charles in Woburn.
1934: Fr. Merritt dies and the parish holds a Mass and funeral including more than 100 clergy. This beloved priest was well respected throughout town. Rev. James Lynch is acting pastor until Rev. Aloysius S. Malone is assigned as new pastor. Fr. Malone organizes a conference of the Society of St. Vincent de Paul to assist the needy of the parish. He begins extensive renovations of the church, which were completed before his death in 1940.
1940: Solemn High Mass and Funeral for Fr. Malone, who died unexpectedly in Winchester. Rev. John O’Riordan is appointed pastor.
1942: Infamous Coconut Grove Nightclub fire in Boston claims the lives of nine Winchester residents, two of them young women parishioners of St. Mary’s.
1948: Lt. Col. John Hanlon of Winchester runs a drive to collect sheets from Winchester residents to replace sheets loaned to his 502nd Airborne battalion in 1944 by the villagers of Hemroulle, Belgium for winter camouflage. He returns in February with the sheets to Hemroulle. In gratitude, they gave him 10 Stations of the Cross from their chapel to be given to each church in the Winchester. The event was detailed in Life Magazine.
1950: St. Mary’s High School closes.
1951: On January 7, the Boston Consul of Belgium presented the 10 Stations of the Cross paintings to the church leaders in a ceremony at the high school. Rev. John O’Riordan, who played an active part in the story, received the 9th Station of the Cross on behalf of St. Mary’s.
1952: Rev. John O’Riordan retires due to poor health. Rev. John Manion is appointed pastor. St. Mary’s Hall is built.
1959: Rev. Manion is elevated to the rank of Monsignor. He began the tradition of saying three ‘Hail Mary’s’ for the deceased at the end of the Mass, a traditional that persists to this day.
1964: St. Mary’s parish again divided to form St. Eulalia parish, which comprised of the western section of Winchester and part of Arlington. Monsignor Manion played an integral role in its establishment and Manion Hall was named in his honor.
1969: Monsignor Manion retires due to ill health. Rev. James A Garrity is appointed pastor. He installs stained-glass windows depicting Marian events. He dies in Boston in April. In response to the Second Vatican Council the first Pastoral Parish Council was formed.
1973: Sisters of St. Joseph cease teaching at St. Mary's school.
1974: Rev. Garrity retires due to ill health. Rev. Arthur L. Reardon is appointed pastor and assumed duties on July 21.
1976: Bicentennial of the nation and 100th anniversary of the parish. A committee is formed to organize the celebration events. Centennial Mass led by Humberto Cardinal Mederios and concelebrated with bishops and priests. All priests and former parishioners are invited to attend. A banquet followed at the Copley Plaza Hotel. Reconstruction of the upper section of the Church tower.
1981: The Marist Missionary sisters lease the convent.
1983: Rev. Paul G. Kelley joins St. Mary’s as Parochial Vicar.
1985: Rev. Dennis F. Twomey, M.S.W., Ph.D. is appointed pastor. He is installed on November 17 by Bishop Mulcahy.
1986: Sr. Patricia Burke, SMSM, is appointed Pastoral Associate. First Annual Memorial Mass for St. Mary’s Parishioners.
1987: Rev. Stephen A. Koen II, M. Ed, who had previously been an associate pastor at St. Mary's, returned as Pastor, and is installed by Bishop Mulcahy.
1991: The Marist Missionary Sisters vacate the Convent. Sr. Patricia Burke stays on as Pastor al Associate.
1992: Under the direction of Fr. Koen, Parish Visitation takes place with positive feedback. The parish composes “A Vision of Parish" which includes reports on all activities and a parish history.
1993: A new, handicapped accessible ramp, made possible by a substantial donation of Mr. E. Joe McCarthy, was dedicated. Fr. Koen is reassigned to the parish of Mary Immaculate of Lourdes in Newton. Rev. Richard Messina is appointed the 14th pastor. Very Rev. Francis X. Turke installs him on September 19th. Fr. Messina undertakes a survey of the entire parish property. Plans a new Chapel and Gathering Room in the Lower Church.
1994: St. Mary's chosen to participate in the deacon internship program. During the next three years three deacons, Rev. Wayne Belschner, Rev. Timothy, and Rev. David Barnes each complete a one year internship in the parish family.
1996: Sister Patricia resigns and takes an assignment as Parish Administrator in West Virginia. Salvatore Caraviello joins as the Pastoral Associate. Gathering Room is dedicated with Mass and solemn procession. A plaque with names of donors is erected.
1997: Salvatore Caraviello assumes position of Director of Ministries with responsibilities for all ministries, the CCD program and all Youth activities. Winchester’s Catholic parishes began meeting as a “Cluster” to produce contingency plans for the coming shortage of priests and to work on collaborative projects. Parish is reviewed by Bishop Irwin and a visitation book is compiled on the parish history and current events.
1998: The former convent becomes the new parish center, and planning for renovations and handicapped accessibility start. The gift of the 9th Station of the Cross given by Hemroulle. Belgium in 1995 is located at the parish, restored, and hung on the church wall with a memorial plaque. St. Mary’s receives its first Permanent Deacon, Deacon James Kerrigan, who works here on a part-time basis. The Winchester Catholic parishes gather on the Town Common to celebrate Mass. Over 500 parishioners and clergy attend, this has now become an annual event.
1999: The parish website goes online. Initial planning begins for introducing Stewardship. Rev. Richard C. Beaulieu joins as Parochial Vicar.
2000: First Stewardship campaign begins, focusing on concepts of Time, Talent and Treasure. Summer project of lower campus re-beautification process undertaken.