Wilbur was 12 years old when his father died. Because he was so needed on the farm, he took his last two years of high school at home in one year. In 1909, he graduated from Johnson Normal School in Johnson, Vermont and went on to get a degree from Bishops College in Lennoxville, Quebec. He taught school and was the principal of Waterloo High School. His salary was $1,100.00. a year. He and his Brother-in-law Isaac Drew built a cottage at Bacon's Bay on Lake Massawippi. Lumber for this was cut on Isaac Drew's farm and hauled on a double wagon from Barnston to Bacon's Bay. Wilbur was engaged to marry Beatrice Meade who lived with her brother Bert and his ailing wife. The story goes that Bert was reluctant to have his sister marry as he needed her to care for his wife and managed to break up the love affair. Whether or not he had such influence cannot be known for sure. In any case, Beatrice did break the engagement, an action which prompted Wilbur to enlist in the army. Beatrice never did marry. Wilbur had never been too strong and perhaps would not have passed the physical had not the country's need for soldiers been so great. His last leave before being shipped overseas was spent at the cottage at Bacon's Bay.