Skiing was a huge part of Derek Cressey’s life.

The Windham native grew up skiing. He lived out West for a year to ski. He and his wife skied at Sunday River before their wedding ceremony. They skied at Sugarloaf every weekend, including a four-day stretch from Feb. 16-19. It was the last time they skied together.

Family and friends were shocked to learn Cressey died of injuries sustained in a skiing accident in Breckenridge, Colorado, on March 8.

A news report about the accident said it occurred at the Breckenridge ski resort around 9:50 a.m. that day near the Northstar run, an intermediate trail. Cressey hit a tree and was transported to a first aid room, where he died of his injuries. News of his passing spread quickly on social media.

“I didn’t believe it was true,” said Seth Nielsen of South Portland, one of Cressey’s closest friends. “We skied together our whole lives. We skied. We went fast. We crashed. We would always bounce back. It’s how we skied. You might get hurt, but you never think something like this would happen. He was a fantastic skier.”

Cressey, a Windham business owner, was 37.


He was married to Erica Cressey, and the couple have two young sons, Brecken, 5, and Kellan, 2.

“He was the most gentle, caring and sensitive guy you could ever meet,” his wife said Tuesday. “He was intimidating when he walked into a room, but two seconds later everyone had big bear hugs. He was a gentle giant. If he knew you, he loved you.”

The tragedy comes just six months after Cressey’s father, longtime Portland firefighter Capt. Dean Cressey, died on Sept. 30.

Cressey was devastated by his father’s death, saying in a news story that he and his father were best friends. He said they rode Harley-Davidson motorcycles together and took trips to Laconia Motorcycle Week in New Hampshire.

Cressey was a 2000 graduate of Windham High School. He worked for Titan Mechanical and W.H. Demons before starting his own business, DC Plumbing and Heating, in 2013. He installed plumbing and heating systems in new homes throughout southern Maine. His wife said he had two employees.

“He always told me that he loved what he did,” she said. “He was proud of his work. He prided himself on doing things the right way.”


For Cressey, family was everything.

His wife reminisced about life together, from growing up in Windham to skiing at Sunday River on their wedding day. She said they started dating nine years ago.

“We were skiing at Sunday River one day and we were single at the time. I asked him what his problem was and why he hadn’t asked me on a date,” she said, laughing. “We’ve been together ever since.”

They were married on Dec. 4, 2010, at the Bethel Inn Resort. Just before the ceremony, they went skiing at Sunday River. Onlookers cheered them on.

“It’s not every day you see a bride in her dress and a groom in his tux skiing,” she said.

A highlight of Cressey’s life was being a dad. He and his wife took the kids skiing at Sugarloaf every weekend. He coached his son’s soccer team and was excited about plans to take the boys fishing this summer.


His wife touched on the moment he would come home after a long day to be with her and the boys. She started crying.

“He was incredible,” she said. “He was the light of their lives. When he opened the door, it didn’t matter what they were doing. They ran for his hugs and kisses.”

Cressey is survived by his mom, Joleen Guidi of Windham. He also leaves a sister, Kendalee Cressey of Falmouth. His sister said they were best friends.

“We’re a very close family,” his mother said on Tuesday. “He was just a great kid. He was a great guy and a great father. He was something special.”

Mourners will gather from 3 to 6 p.m. Friday at A. T. Hutchins Funeral Home in Portland. A reception will be held from noon to 4 p.m. Sunday at Rustler’s Steakhouse in Windham.

Melanie Creamer can be contacted at 791-6361 or at:

Twitter: MelanieCreamer

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