On October 13th, 1859, 8 Master Masons living in Milford decided to petition the Grand Lodge of the State of Connecticut for a dispensation allowing them to confer the three degrees of Masonry.  The new Lodge, named Ansantawae, after the Paugusset Indian who deeded the original plot of land to the first English settlers in Milford, was granted this dispensation on October 21, 1859.  The first meeting was held in the Odd Fellows Hall on October 24th, 1859, with Thomas A. Dutton as Worshipful Master.  9 members were raised that year, mostly by brothers of St. Johns Lodge #8, and King Hiram Lodge #18.  It only took 7 years to reach 100 members, as the year 1866 brought 14 new members, and membership was at 104 by the end of the year. 

For the next twelve years, there were several committees formed to find a more suitable meeting place.  Finally, on February 15th, 1878, the lodge bought the property which it still occupies to this day at a cost of $1,000.00.  The cornerstone was laid for our new building on August 6, 1878, with 33 members and over 200 visiting brothers from sister lodges. 

 Over the next 30 years, interest in the lodge ebbed and flowed, not reaching 150 members for the first time until 1910, during the third term of Arthur H. Platt.  During the following decades, interest in the lodge multiplied, taking only 8 more years to put membership over 200 (1918), another 4 years to raise it over 300 (1922), and 7 more (1929) to put us over 400.  To give an example of how much interest there was in the lodge during the '20's, on May 9th, 1922, 86 members of our lodge travelled to Adelphi Lodge #63 in Fair Haven to perform the Master Mason Degree.  Some very well known Milford Residents joined during these years, including George J. Smith, and Simon Lake.  The first use of a uniformed Fellowcraft Degree team was on a special communication of March 24th, 1922.  In 1924, our building was expanded, with the additional cornerstone being laid on June 21 of that year.

In early 1925, WM Harry Nodine appointed a comittee to explore the possibility of starting a DeMolay Chapter.  This comittee, led by WB Herbert Ford, reported favorably at the April 2nd, and the first advisory council was appointed.  It didn't take long for Milford DeMolay to have an affect on the membership of the Lodge, as on October 16th of the same year, Bro. J. Edmund Ellis was the first "Senior DeMolay" to recieve his Entered Apprentice degree (the first of many!).

The 1930's and early 1940's were difficult for the lodge, with the Great Depression and World War I, and membership slipped back to just over 300 by 1940.  By the late 40's and early 50's however, there was another time of tremendous growth in the lodge, and membership swelled to 615 by the end of 1957.

1947 brought the first appointment of an Ansantawae brother to the position of District Deputy, as Bro. William Nyquist was given this distinction by MW Bro. Charles Ramage.  In 1955, the lodge laid a cornerstone, marking the start of the second, and final expansion of the lodge building to its' present size.  Throughout the 1960's and 70's, the lodge enjoyed much success.  In 1978, only the second stated communication in the entire history of Ansantawae Lodge to be cancelled was January 20, presumably due to weather.  The first was during the Blizzard of 1888.  Visitations were made around Connecticut, and even to other jurisdictions to perform degrees, making Ansantawae Lodge well known not just to all in Connecticut, but also surrounding states.  It also brought the election of MW Bro. Arthur F. Simpson to the office of MW Grand Master of Masons in Connecticut on April 6, 1977.  It took 118 years to have a brother from Ansantawae elected to this honorable office, but over the next 32 years, it would happen twice more, with the election of MW Kenneth B. Hawkins in 1994, and the newest (who was just elected, and has yet to be installed), RW Charles A. Buck, Jr. in 2009.