Captain Raymond S. Williams

Raymond Scott Williams, born July 13, 1964 died October 7, 2026 after complications from a catastrophic stroke. He went peacefully in the night, resting comfortably at Gosnell Memorial Hospice House in Scarborough.

Ray grew up in Cumberland where his family had generational ties to the community. After living in several different locations throughout his life, he finally settled in Gorham where he lived with his beloved partner Dawn Freeland and their furbaby Chloe.

Ray graduated from Greely High School in 1983 and went on to Southern Maine Community College where he obtained an associates degree in criminal justice.

For as long as we can remember, Ray had always wanted to be a police officer and he achieved that dream by graduating from the Police Academy in 1987. Fresh from the academy, he found himself in his first role as a Reserve officer at Windham Police Department in May 1985 and was hired as a full-time Police Officer on September 4, 1986. That would begin an illustrious career that lasted 38 years. In those 38 years, he served in many roles, including Patrol Officer, Detective, Patrol Sergeant, and Patrol Captain. Among his many accomplishments throughout his career was the creation of the Windham Police Department’s motorcycle program. Over the years, he proudly escorted countless charity toy runs, memorial rides, and community events throughout the State of Maine. He also served as a Range Officer and Firearms Instructor, helping to train and mentor generations of officers. One of Captain Williams most notable achievements was being a member of the first class of Drug Recognition Experts certified in the State of Maine. Ray retired with the Windham Police Department on May 5, 2023. In true Ray fashion he couldn’t stay retired, however, and joined Walden Security in June 2024 as a CSO Court Security Officer for the Federal Courthouse in Portland Maine. He also joined Falmouth Police Department in April of 2024 as a part time Patrol Officer and if that wasn’t enough, he rejoined Windham Police Department as a reserve officer as well. He remained in those positions till his passing.

In addition to his incredible career, Ray was a beloved member of the Windham community. Everyone knew Ray and if you didn’t, just give him a minute. They didn’t call him the unofficial Mayor of Windham for nothing. He was smart, funny, humble and easy going. It took a lot to ruffle his feathers. He was a Scotch connoisseur, a Bourbon expert and loved a good local IPA. Pair that with a good or not so good cigar and he had the perfect day.

Ray was a registered Maine Fishing Guide and loved to fish and if he wasn’t working, he was out on the boat with his trusty boat dog Chloe waiting to yell “fish on!”. You could always find him on Sebago at any given time whether it was for open water fishing or ice fishing. Any day on the water, frozen or not was the best day for Ray. He was a really good backyard mechanic, lover of all dogs and animals and a really good cook. We’ll miss his homemade pizza.

Ray and Dawn were together for almost 10 years. Over the years, they had many adventures which included weekend getaways to Boston for a Red Sox game, trips to the Cape for relaxation, bird hunting trips up to Moosehead and weeklong summer vacations on the shores of Moosehead lake. They were also able to visit Ireland and Great Britain and most recently a bucket list trip to Yellowstone National Park. They truly had a beautiful relationship and were lucky to find each other.

Ray was dedicated to his family and friends and friends that were family and had ties with Lamoine and Moosehead where he loved to camp, fish, vacation and bird hunt. It will be hard to visit these places without remembering how much he loved being there.

Ray is survived by his beloved partner Dawn Freeland, his sister Rhonda Williams, his brother Brad Williams, sister in law Renee Williams, nieces Shana Bennett, Kelsey Williams and Kendra Williams, his nephew Ethan McConnell, his great nephew Corey and his great nieces Jessa, Fiona, Sophia, Blake and Addison along with his Lamoine family and brothers and sisters in law enforcement. He is predeceased by his son Nicholas Williams and his parents Scott and Nancy Williams.

A Funeral Service honoring Captain Williams will be held at 1:00 PM on Sunday, October 18, 2026, at Windham Performing Arts Center (Windham High School), 406 Gray Road, Windham. Car pooling is encouraged.

In lieu of flowers, find a way to pay it forward. After all, that’s how Ray lived his life.

Arrangements are under the direction of the Conroy-Tully Walker Cremation, Funeral & Gathering Center of Portland, proudly honoring those who serve and protect our communities.