Oliver L. Aylward, 31, of Ashland died unexpectedly Wednesday, August 19, 2026. Born in Natick, he was the son of Ruth (Brigandi) Aylward and the late Joseph Richard Aylward. Ollie attended Ashland High School and went on to create Ollie’s Landscaping, serving the Metrowest area. 

He loved fishing and kayaking, cooking (pasta-making was a particular favorite) and was a music-enthusiast, being a talented guitar player and composer. He loved to make other’s laugh, was a talented tradesman and very artistic. Ollie also played hockey and lacrosse, attended karate in his younger years, and also was very fond of riding his dirt bike. Most of all, Ollie loved his family and friends - he was happiest surrounded by the people he loved, and always there to lend a helping hand and somebody to count on. Ollie was uniquely Ollie, and had a way of turning even ordinary moments into stories told and laughed about for years to come. 

Ollie is survived by his daughter, Elayna Aylward, mother, Ruth Aylward, and sister, Zoe Aylward, along with many aunts, uncles and cousins. 

A celebration of life will be held Saturday, August 29th at 2:00 PM in the Chapel of the Matarese Funeral Home, 325 Main St. Ashland, MA. Visiting hours will be held Saturday from 12:00-2:00 PM prior to the service in the funeral home. z

In lieu of flowers or other gifts, Oliver’s wish for those to honor his memory would be to consider making a contribution toward the future education of his daughter, Elayna. Contributions can be made directly at: https://gofund.me/8e023211a