October 12, 1888 – Company organized at the quarters of Chemical Engine Company 4 at 4246 Washington Street , corner of Poplar Street, Roslindale. The company was assigned a ladder truck rebuilt by the BFD Shops, equipped with 15 ladders of varying lengths.
General Order #305, dated February 18, 1888, announced the establishment of Ladder Company 16.
July 28, 1915 – The horse-drawn ladder truck was replaced by a 1915 Christie 2-wheel Front-Drive motor tractor, Shop # 215T , attached to an 1888 Boston Fire Department Shops combination ladder truck.
September 18, 1923 – The 1915 Christie motor tractor was replaced by a 1923 American LaFrance, Type 14, motor city-service combination ladder truck , Serial # 4363, Shop # 234.
1939 – Company received a 1923 American LaFrance, Type 14, motor city-service combination ladder truck , Serial # 4361, Shop # 233.
April 11, 1949 – The 1923 American LaFrance city-service ladder truck was replaced by a 1949 American LaFrance, ‘700 Series’ 65ft junior aerial ladder truck, Serial # L3846, Shop # 266.
June 11, 1959 – Company moved to a new firehouse at 315 Cummins Highway , corner of Canterbury Street, Roslindale. The old firehouse at 4246 Washington Street was closed and later demolished for a new library building.
November 21, 1961 – The address of the firehouse was changed from 315 Cummins Highway to 945 Canterbury Street.
1965 – Company received a 1952 Pirsch 65ft junior aerial ladder truck, with 150gal. booster tank, Serial # 2050, Shop # 278.
1968 – Company received a 1962 Seagrave 85ft tiller aerial ladder truck, Serial # N310, Shop # 212.
1973 – Company received a 1970 American LaFrance 100ft tiller aerial ladder truck, Serial # 12-1-1950, Shop # 203.
October 23, 1976 – Fire Fighter Richard P. Sheridan, Ladder Company 16 (detailed to Aerial Tower 2), died in the Line-Of-Duty from a collapse of a brick wall while operating at 22 Simmons Street, Roxbury, Box 2241, 3 Alarms.
1977 – Company received a 1973 Maxim, F Model, 100ft aerial ladder truck, Serial # 3128, Shop # 208.
1978 – Fire Fighter John L. Cheatham, Ladder Company 16, was awarded the Roll-Of-Merit. Citation
November 2, 1984 – Company received a new 1984 Emergency One 110ft rearmount aerial ladder truck, Serial # 3741, Shop # 202.
December 7, 1992 – Company received a new 1992 Emergency One 110ft rearmount aerial ladder truck, Serial # 10933, Shop # 222.
1992 – Fire Fighter Thomas J. Blake, Ladder Company 16, was awarded the Roll-Of-Merit. Citation
2002 – Fire Fighter Robert J. Ryan, Ladder Company 16, was awarded the Roll-Of-Merit. Citation
2003 – Fire Fighter Brian D. Burke, Ladder Company 16, was awarded the Roll-Of-Merit. Citation
July 18, 2008 – Company received a new 2008 Emergency One 110ft rearmount aerial ladder truck, Serial # 134053, Shop # 245.
May 15, 2015 – Company received a new 2014 KME 109ft aerial ladder truck, Serial # 9582, Shop # 259.
2015 – Fire Fighter Brian D. Burke, Ladder Company 16, was a warded the Roll of Merit for his actions on Greenwood Avenue, Hyde Park, on November 21, 2015. Citation
2015 – Five members of Ladder Company 16, Fire Lieutenant Scott R. Boyle and Fire Fighters Jay R. Gormley, William J. Malcolm, Brian D. Burke and Jason G. Anderson, were awarded the Commissioner’s Unit Citation for their actions on Greenwood Avenue, Hyde Park, on November 21, 2015. Citation
2018 – Four members of Ladder Company 16, Fire Lieutenant William McGuirk and Fire Fighters Brian D. Burke, William J. Malcomb and Matthew J. Marian, were awarded the Commissioner’s Unit Citation for their actions at 6 Rainier Road, Mattapan, on October 1, 2018. Citation
February 10, 2022 – Company received a new 2021 Emergency One ‘Metro’ single-rear axle, 100ft rearmount aerial ladder truck, Serial # 144024, Shop # 282.
2022 – Four members of Ladder Company 16, Fire Lieutenant Jay R. Gormley, and Fire Fighters William J. Malcomb, Matthew P. Marian and Nicholas A. Santangelo (detailed from Ladder 29) were awarded the Commissioner’s Unit Citation for their actions at 3927 Washington Street, Roslindale, Box 2617, on November 8, 2022. Citation