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An Annual Meeting of the members was held at a location in New York City each year. The earliest meetings appear to have been held at the Friends' Meeting House on East 20th Street in New York City. Subsequent meetings were held at the Friends' Seminary at Rutherford Place and East Fifteenth Street in New York City, and in 1907 and later at the Underhill Society Library at 198 Rutledge Street in Brooklyn, New York. The Annual Meeting was occasionally supplemented by a February Meeting in the earlier years of the Society. Over time having one meeting a year appears to have become the precedent. In addition to these regularly scheduled meetings, several family reunions have been held through the years.

  • 1893, 1st Annual Meeting, Friends' Meeting House, Fifteenth Street and Second Avenue. David Harris Underhill read a history of the Underhill family on February 22, 1893.[2]
  • 1893, 1st Family Reunion (planned) on September 21, 1893.[2]
  • 1894, 2nd Annual Meeting
  • 1894, 2nd Family Reunion (date and location unknown)
  • 1895, 3rd Annual Meeting
  • 1895, February Meeting, Friends' Meeting House. Robert Underhill chaired meeting with thirty members present. Secretary reported Society has eighty members.[5]
  • 1895, 3rd Annual Reunion, Women's Institute Building, Palisade Avenue, Yonkers, New York. Address of welcome from Major Frederic Shonnard and response by Reuben H. Underhill. Piano solo by Prof. Van Alstyne and an ode to Capt. Underhill was read by Fanny Crosby.[6]
  • 1896, 4th Annual Meeting
  • 1897, 5th Annual Meeting, Friends' Seminary on February 22, 1897. George W. Cocks of Glen Cove spoke on the life of David Underhill, youngest son of Capt. John Underhill. Proposal was made to celebrate Capt. John's three hundredth birthday in New York City in October 1898.[7]
  • 1898, 6th Annual Meeting
  • 1899, 7th Annual Meeting, Friends' Seminary. Estelle Skidmore Doremus delivered an address on "The Life of Capt. John Underhill."[8]
  • 1900, 8th Annual Meeting
  • 1901, 9th Annual Meeting
  • 1902, 10th Annual Meeting
  • 1903, 11th Annual Meeting
  • 1903, Family Reunion held on October 7, 1903 at Underhill Burying Ground followed by a luncheon and program at the house of John and Hannah Bayles. George W. Cocks read an "Account of the Old Underhill House at Killingworth."
  • 1904, 12th Annual Meeting
  • 1905, 13th Annual Meeting, Dr. Robert Ogden Doremus named an Honorary Member. A Memorial Sketch for Estelle Skidmore Doremus was read by David Harris Underhill.
  • 1906, 14th Annual Meeting, John Torboss Underhill presided. David Harris Underhill read a paper on Edward Underhill, "the hot gospeller," whose religious views got him confined in the Tower of London. Report of monument committee made. Membership reported at 140.[9]
  • 1907, 15th Annual Meeting, Underhill Society Library. Essay on Edward Underhylle The Hot Gospeller read by David Harris Underhill.
  • 1908, 16th Annual Meeting
  • 1908, 17th Annual Meeting. Total number of members reported at 116.
  • 1909, 18th Annual Meeting, Underhill Society Library.

Note: Data for Annual Meetings between 1910-1984 is not as of yet readily available.

  • 1985, Rothmann's Steakhouse, East Norwich, New York.
  • 1986, Bar Association Building in Mineola, New York, with a bus tour after lunch.
  • 1987, Boston, Massachusetts at the Copley Plaza with a tour of the city.
  • 1988, Williamsburg, Virginia and a walking tour of the Old Town.
  • 1989, Greenport, New York with tours to a museum and the grave of Helena, first wife of Capt. John Underhill.
  • 1990, Louisville, Kentucky with tours of Churchill Downs.
  • 1991, Charlestown, South Carolina in connection with the reunion of the USS Underhill men.
  • 1992, Tarrytown, New York with a visit to Croton Point and Isaac Underhill house.
  • 1993, Mackinac Island, Michigan
  • 1994, Fredericton, Canada, where we saw different Underhill areas.
  • 1995, Uniondale, New York, and a walking tour of Oyster Bay, New York.
  • 1996, Santa Barbara, California
  • 1997, Savannah, Georgia
  • 1998, St. Louis, Missouri with a bus trip around and visited a zoo.
  • 1999, Mystic, Connecticut with museum, whaling vessel and lighthouse tours (lighthouse in Kensington nearby) - Meeting Events.
  • 2000, Louisville, Kentucky, visited Shaker Village of Pleasant Hill, Kentucky Historical Society Museum in Frankfort and Old Stone Inn in Simpsonville.
  • 2001, San Antonio, Texas (canceled due to events of 9/11)
  • 2002, Saratoga, New York
  • 2003, Belleville, Michigan
  • 2004, Grand Rapids, Michigan
  • 2005, Asheville, North Carolina and the Biltmore Mansion
  • 2006, Vancouver, Canada
  • 2007, Fort Worth, Texas
  • 2008, Oyster Bay, New York - 100th anniversary of the Capt. John Underhill Monument dedication at Burying Ground on Long Island.
  • 2009, Deerfield, Massachusetts
  • 2010, Rapid City, South Dakota in the Black Hills Mount Rushmore National Memorial, Crazy Horse Memorial, Badlands National Park.
  • 2011, Croton on Hudson in New York’s Hudson River Valley at the Edith Macy Conference Center. Croton Free Library Westchester County Parks.

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