When a crowd of islanders filled Ober Park for the last of this summer’s concerts there recently, they danced, swayed and sang along to the sounds of the oldest band on Vashon, a big band that plays songs from the past — and a band that many hope will last long into the future.

The Portage Fill plays music primarily from the 1930s and ’40s, drawing from artists such as Glenn Miller, Benny Goodman, Duke Ellington, Count Basie and Frank Sinatra. A staple at Strawberry Festival, where the band opens the music on Saturdays and plays for the popular street dance Saturday evenings, Portage Fill dates back more than 40 years. In a recent interview, trumpet player Lou Engels recalled the group’s first practice, which took place in his home. The year, “the best we can remember,” he said, was 1973. Originally a small combo started by his neighbor, pianist Bill DeGleria, the group was christened the Portage Fill-Harmonic. It later transformed into a big band under Seattle trumpet player and Vashon music store owner Monte Sewell. Engels, who has played the trumpet since he was 9, has played with the band since that first night the group met in his Portage living room — and, he said, the band is going strong.

“The group, now 16 strong plus two vocalists, is sounding better than ever,” Engels said last week, taking a break at his long-time business, Engels Repair & Towing.

Pete Welch, who schedules musical happenings on Vashon for Vashon Events, recently spoke to the band’s popularity and its ability to get people of all ages up and dancing.

“They always draw a crowd,” he said, commending the instrumentalists, as well as the singers, Maggie Laird and Lou Mangione.

“When Lou and Maggie get up there, it is almost like you are stepping back in time. It’s just beautiful. They’re crooners,” he said.

Tony Willing, who has played with the band for over 20 years, is the group’s musical director, a position he has held for approximately the last decade. Years ago, Willing said, islander Dan Brown had been in the band, but was leaving and selling his keyboard. Willing stepped in and bought Brown’s keyboard — and more.

“I essentially bought his spot,” Willing said, adding that he had known about Portage Fill, but had not known how to get in it. “I jumped at the chance.”

Willing studied music at Western Washington University and plays a variety of instruments. About five years after he joined, the band was facing a trombone shortage. Willing shifted to that instrument and has remained with it ever since.

Over the years, the band has waxed and waned, but like Engels, Willing said he believes the band’s hey day is now. He attributes that in part to the resurgence of swing dancing, increased interest in dancing overall — thanks to a little help from Dancing with the Stars — and to big band music itself, which he said has a vitality and energy all its own. He added that the music calls for improvisation, which is an important element of its appeal.

“When you get a bunch of creative people working like that, the energy just builds,” he said.

Engels is quick to credit the talent of the people involved now and over the years, noting the band has included everyone from high school music teachers to professional musicians. He has lost track of how many people have participated.

“It could easily be 50,” he said.

Those involved with the band say that strong musical ability is needed. Trumpet player Dennis Williams has played with the band for more than 20 years and says that both technical skills and a feel for swing are important for playing big band music; simply being classically trained might not be enough. Moreover, he said, most everyone plays different parts, even those playing the same instruments. Each section has a leader, and the members of the section are expected to follow that leader in terms of style, Williams added. Sections also have members who play the solos and improvise. Williams, who is the trumpet section leader, noted that fellow trumpet player Richard Person typically takes those. In fact, it is Person’s solos that Williams counts among his favorite band memories.

“He is a phenomenal soloist,” Williams said. “He is unique and creative every time.”

Laird, one of the band’s two vocalists, recalls how she first became involved with the band more than 20 years ago. Her car broke down, and she had to get a tow from former band member Pete Bruchas, who ran a tow business out of the Shell station. The two got to talking about music on the trip to her home; he was in the band and told her they needed a singer.

Laird, who had come from a rock background, said she was intrigued, as she had never sung with a big band before. Little by little, she started singing with the group. She noted that singing with a big band presents unique challenges. It requires learning the arrangements — not just the lyrics and the tune — and learning to sing with a large number of people and a large number of horns, which she called “sonically unusual.”

Now, she sings with two big bands, Portage Fill and the Federal Way Symphony Big Band.

She distilled down to the basics what has kept her involved with big band music all these years.

“It is super fun,” she said.

Laird’s fellow singer in the Portage Fill, Mangione, is one of the newest members of the band; he joined in 2008. He first sang with the band at a Northwest Folklife performance Laird could not attend — and he has not left yet.

Mangione grew up with the music of Tony Bennett, Dean Martin, Perry Como and Frank Sinatra — and has loved it since he was young.

“It was a chance in a lifetime when they asked me to be part of the band. It is something I had always wanted to do,” he said.

The experience has not disappointed.

“That amount of sound behind you is amazing. Plus you are singing with some of the most incredible musicians on the island,” he added.

One of the pieces Mangione said showcases the band’s talent and cohesion is “Children of Sanchez,” by Chuck Mangione — who is Lou’s distant cousin. “Come Dance with Me” by Frank Sinatra made Lou Mangione’s list of personal favorites — as did some others.

“I really love ‘Kick in the Head’ because it wails,” he added. “I love the way Dean (Martin) Sang.”

Laird provided some favorites as well, ranging from “swingy ones,” such as “It Don’t Mean a Thing” to slower songs, including “The Very Thought of You.” But choosing was difficult.

“I have to say I love every single song,” she said.

With a band repertoire of 375 songs, director Willing has ample material to pick for any show. He chooses depending on who is playing, he said, as well as whether the gig is a dance or more of a show. Sometimes he adds in a song the group has not played in awhile, and there are songs they always play. He added that he aims for a mix of vocals for the singers as well as tunes for the band — and he tries not to wear out the brass players.

Over the years, the band has played in many shows both off and on the island, ranging from the Quinnalt Casino to the Open Space for Arts & Community for President Obama’s inauguration party. Given the band’s size, the Portage Fill cannot play just anywhere — whether for shows or for practice, which it currently gathers for twice a month at Williams Heating. While it has a long history on the island, members also look to the future. To that end, Willing said sometimes high school students will sit in. It gives them a sense of what the music is like and the experience of playing with seasoned musicians.

Trombonist David Hackett noted he was 6 years old when the band formed; he has played in the group for 12 years, and considers himself among the newest members.

“When I see young kids dancing at the street show, I wonder (and hope) that they will be joining us in 20 years or so. It is a great group and I hope we play together for at least another 45 years,” he said.

Trumpeter Williams attributed the longevity of the group to members’ shared love of the music.

“We have as much fun playing as people do listening,” he said.

Willing agreed.

“I am going to play in the Portage Fill as long as I can,” he said, adding with a laugh, “And since I am the director, I call the shots.”

There are other benefits to being in the band, he said: “Music keeps you young.”