Hugh Loring Prestwood, a legendary Nashville songwriter who for decades lived in Greenport and played local clubs, bars and vineyards, died last month in Nebraska at the age of 82, following a stroke.
Prestwood, a Nashville Songwriters Hall of Fame member, was discovered by artist Judy Collins — who turned his song “Hard Time for Lovers” into a hit — and went on to write number one hits for Crystal Gayle and Randy Travis. His tune “The Song Remembers When,” recorded by Trisha Yearwood, won the Nashville Songwriters Association’s 1993 Song of the Year and an Emmy for “Outstanding Achievement in Music and Lyrics,” when it was featured in Ms. Yearwood’s Disney Channel musical special “Trisha Yearwood: The Song Remembers When.”
“Hugh Prestwood was a poet,” Ms. Yearwood wrote in a post on X, formerly Twitter, last month. “ ‘The Song Remembers When’ is one of the greatest songs ever written, and I’m the lucky girl who got to sing it. It paints the beautiful picture of the power of music. We’re all lucky that Hugh decided to be a writer. I will miss his voice.”
Mr. Prestwood’s songs were also recorded by Jimmy Buffet, James Taylor, Jerry Jeff Walker, Tanya Tucker and Conway Twitty, among many others.
“Prestwood’s folk-meets-country stylings leaned in an adult-contemporary direction that benefited artists, including torch song stylists like Crystal Gayle (1983’s “Sound of Goodbye”), neo-traditionalists like Randy Travis (1989’s “Hard Rock Bottom of Your Heart”), country-to-pop radio stalwarts Shenandoah and traditionalists like Alison Krauss (1999’s “Ghost in This House”),” the Tennessean newspaper wrote last month.
The wordsmith was born and raised in El Paso, Texas, and graduated from the University of Texas with a degree in English.
His wife, Judy Ahrens, an award-winning former Suffolk Times photographer who now lives in Lincoln, Neb., said in the early 1970s, Mr. Prestwood lived in New York City and played at open mic nights in Greenwich Village.
The folk legend Tom Paxton caught one of his shows and went up to Mr. Prestwood to compliment him after his set.
“ ‘Do you think you could get this tape to Judy Collins?’ ” Mr. Prestwood replied, holding out a tape, according to Ms. Ahrens. “And he said, ‘Sure.’ So Judy Collins called him up and said, ‘I love your songs.’ And she ended up cutting five of his songs, and one of them was ‘Hard Time for Lovers.’ So that was his big break. [Ms. Collins] set him up with some big cheese in Nashville, and his career took off.”
Ms. Ahrens used to photograph Mr. Prestwood playing with Nancy Baxter at The Cinnamon Tree, a restaurant on Main Street in Greenport.
“It was the ‘in’ place to be in the late 1970s and early ’80s,” Ms. Ahrens recalled. “It was wild. It was great.”
Mr. Prestwood also spent more than 20 years teaching advanced songwriting at the New School in Manhattan.
By the early 1980s, he was living with his teenage son in New York City and wanted to move to the country. Father and son packed up and headed to Greenport.
In 1983, Ms. Ahrens was dispatched by The Suffolk Times to take Mr. Prestwood’s picture — after his song “The Sound of Goodbye,” recorded by Ms. Gayle, topped the charts.
“I went to take a picture of him, and I ended up staying for a very long time,” she said last week. “The sparks flew, and we’ve pretty much been together ever since.”
Former Suffolk Times publisher Troy Gustavson was friends with the late songwriter and his wife.
“He had a very droll sense of humor,” Mr. Gustavson said, “He was very intelligent, and that came through as soon as you spent any time with him.”
He said Mr. Prestwood and Ms. Ahrens were “inseparable.”
“I think Judy was the love of his life, and he definitely showed that in so many ways …you really never thought of one without the other.”
Bridget McMahon, a longtime friend of Mr. Prestwood and Ms. Ahrens, said the songwriter was a local treasure from the time he moved to Greenport in the early 1980s until he left town two years ago. In the early 2000s, Mr. Prestwood began headlining an annual all-star country music fundraiser concert, the Wine Press Concert Series, at Borghese Vineyards in Cutchogue to benefit the East End Arts Council (now East End Arts).
“Hugh would invite all his songwriting friends from Nashville,” Ms. McMahon recalled. “He was very much a person who cared about the community and the arts and was happy to give his time to raise money for the East End Arts Council.”
She said everyone always had a great time at the concerts and after parties.
“Hugh and Judy had a tremendous amount of friends here in Greenport, and they always had a party afterwards at the house, and it was just great fun. Hugh and Judy loved to be around their friends, enjoy their friends’ company and particularly to share music.”
Ms. McMahon’s husband, Dennis, said that “the musicians would come back to the house and people would, of course, bring an instrument, and it wouldn’t be long before somebody would break out into a song or something and pick a corner to just play something quietly with somebody listening.”
It was Mr. McMahon who did a top-to-bottom restoration of the Victorian mansion on First Street where Mr. Prestwood and Ms. Ahrens lived. He also built Mr. Prestwood a garage studio to record music, and then a second studio in the attic.
“He never used the garage studio,” Mr. McMahon remembered. “He liked to get up in the middle of the night when he had a thought or a lyric, and he would go up and write.”
Ms. Ahrens remembers that time well, saying, “He was not the best sleeper, so he would go write a song up there.”
She said that their time living at 519 First St. was “one of the best times of our lives — just totally renovating that house. It was so much fun.”
The McMahons consider themselves lucky to have been friends with Mr. Prestwood and Ms. Ahrens for all those years when Mr. Prestwood’s career was riding high.
“We heard about 20 years of his firsthand, newest and latest songs,” Mr. McMahon said.
Ms. Ahrens said her husband never co-wrote songs with other songwriters.
“He wrote all the music and all the words himself, which was very unusual in Nashville. Sometimes five people write a song together down there,” she said, adding that her husband felt like a “painter who didn’t want anyone else to grab the brush.”
For years, the couple reveled in sunset solstice parties at 67 Steps Beach in Greenport, and spending nights on their power boat in Peconic Bay.
“Hugh loved Greenport,” Ms. McMahon said. “He really loved it. He just loved the people here, the nature, the community. He felt it was a very special place. This was really home for him.”
Since his death, Ms. Ahrens has struggled to adjust to the loss of her husband of 37 years.
“He was great,” she said wistfully. “He was my everything — he really was. We never had children. He had two grown children from his first marriage, but we never had any children, so we were each other’s everything. So it’s hard.”
Mr. Gustavson said that by the 1970s, Greenport had experienced some tough times, but underwent a renaissance beginning in the late 1970s.
“By the time Hugh got here, it was starting to rebound,” Mr. Gustavson said. “Hugh was really instrumental in the revival of the village, because that music scene began to have an impact here — through Hugh, largely — because by the mid-1980s, he’d written a number of country and western hits.”
Mr. Gustavson said his friend was “laid back, not flashy at all, and I think the village really appealed to him … He could have been in any number of flashier places than Greenport. But Greenport was his style.”