In September 1916, a grand reunion of former Pitts Point Academy students was held on the grounds of the former school. The Pioneer News (15 Sep 1916) described it this way.
The Gwynn Reunion
Largely attended and greatly enjoyed.
The Reunion of the former pupils of Prof. W. B. Gwynn at the old academy at Pitts Point last Saturday was a notable event and will live as long life shall last and ever be cherished in memory of scores of devoted students who assembled there to greet and cordially welcome once more (for many, it may the last time) their former loved and now venerable instructor. Nature seemed to smile upon the occasion, the bright sunshine, tempered with gentle breezes made the day an ideal one and many happy, smiling faces as well as cordial greetings and generous hand clasps from long separated friends reflected her brightness and warmth. Prof. Gwynn was at his best. He stood at the entrance gate for quite a while with the same old kindly smile and warm grasp for all his old friends, pupils and more recent acquaintances. But one grasp of his kindly hand was necessary to tell that his whole heart and soul was in the joyous occasion. His three score years sit lightly upon him and few to whom his life's work was unknown, would ever believe him to have past the three score mark or that it had been thirty odd years since he left his work at the old academy for a broader field.
The Program, previously prepared, was carried out to the letter, and the exercises interspersed liberally with music by the Shepherdsville Brass Band, which did itself proud and received liberal rounds of applause, was greatly enjoyed by all present. Neither time nor space permits us to enter fully the details, but the welcoming address by Hon. J. R. Zimmerman, quartet by Messrs Sanders, Ridgway, Bates and Roby, song by Marguerite Sanders and Charles Lee Bradbury were especially good and greatly enjoyed.
One of the leading features was roll call of former pupils: both male and female, many of them answered in person, others by entertaining letters whilst numbers were reported as having "passed over the River" and are awaiting the Roll Call Up Yonder.
The crowning event of the day was the splendid address of Prof. Gwynn towards closing of exercises. For more than an hour, he held his audience spellbound with recital of his experience in years: now away down the streams of time, in the old academy and of events in his busy and successful life since then. Amongst them, he alluded to his experience and the difficulties encountered in starting and establishing The Bullitt Pioneer, of which he was the founder and first editor, which made him feel closer and dearer to the writer, who has always been one of his greatest admirers. He told of his success at Lynnland and how now he is enjoying life on his farm and happy home near Crestwood in Oldham County in company with his dear life's companion and their unmarried daughter and where he says the latch string hangs out and a warm welcome awaits any of his former friends and pupils who chance to come that way. May he long live to enjoy the goods so well won and so richly deserved for he is "The Noblest Roman of them all". God bless him.
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