In his later years, Trailer continued to work in the television industry.
He owned a video production company in Waltham, Massachusetts, and taught on-air performance at Emerson College in Boston, both until his death.
Among his past students are WHDH-TV Channel 7 news anchor Jonathan Hall, Fox 25 morning news host Gene Lavanchy, and Entertainment Tonight correspondent Maria Menounos.
He made regular personal appearances, and performed on occasion, including sets at Boston rock clubs in his later years as a special guest.
Trailer was also a perennial participant in Natick's annual July 4 parade, in which he rode Goldrush.
Trailer’s initial association with the parade ran from 1955 into the early 1980s; Trailer revived the tradition beginning in the early 1990s, continuing it each year until 2012.
In 2013, he was named “grand marshal in memoriam” by Natick Friends of the 4th.

On December 10, 2006, Trailer performed several songs (including the Boomtown theme and some of his own Christmas songs) and signed free autographs for hundreds of fans at That's Entertainment in Worcester, Massachusetts.
The event was part of Trailer's official "50th Anniversary of Boomtown" celebration tour.
Then Worcester Mayor Tim Murray officially proclaimed it "Rex Trailer's Boomtown Day" throughout the city to mark the occasion, and Worcester City Councilor Frederick C. Rushton read the proclamation to the crowd.

In 2011, Trailer donated his three .45-caliber revolvers with staghorn handles to the Massachusetts State Police Museum in Grafton, Massachusetts.
Just prior, the gun shop where Trailer was storing them had gone out of business.
The guns very nearly went on the auction block before Trailer and Michael Bavaro learned of the situation and retook possession.

On September 11, 2011, Trailer appeared at That's Entertainment in Fitchburg, Massachusetts, to meet fans, sing songs and sign free autographs as he marked the 55th anniversary of Boomtown.
The appearance coincided with the tenth anniversary of the September 11 attacks, and Trailer sang a song he had written to honor the victims of 9/11, "I Appreciate You".
He had first performed this song on 2002/09/10 at the Comedy Connection in Faneuil Hall.
He explained the song's significance before that earlier event: "Ever since 9-11, the world has changed for all of us.
We have to stick together, protect each other, and let those you love, respect, and admire know how much you appreciate them."

On December 18, 2011, Trailer wrapped up his 55th Anniversary Tour in Waltham, Massachusetts, at Café on the Common.
Trailer debuted a long-lost Boomtown segment called “Pablo’s Used Cars,” which featured the physical comedy of Trailer’s beloved sidekick, Pablo (actor Richard Kilbride).

In 2012, Trailer continued to appear at events in towns all around Massachusetts.
On September 15, 2012, Trailer was at the Ayer Town Hall, where a gathering of fans joined him for his 84th birthday celebration.
In his later years, Trailer continued to work in the television industry. He owned a video production company in Waltham, Massachusetts, and taught on-air performance at Emerson College in Boston, both until his death. Among his past students are WHDH-TV Channel 7 news anchor Jonathan Hall, Fox 25 morning news host Gene Lavanchy, and Entertainment Tonight correspondent Maria Menounos. He made regular personal appearances, and performed on occasion, including sets at Boston rock clubs in his later years as a special guest. Trailer was also a perennial participant in Natick's annual July 4 parade, in which he rode Goldrush. Trailer’s initial association with the parade ran from 1955 into the early 1980s; Trailer revived the tradition beginning in the early 1990s, continuing it each year until 2012. In 2013, he was named “grand marshal in memoriam” by Natick Friends of the 4th.
On December 10, 2006, Trailer performed several songs (including the Boomtown theme and some of his own Christmas songs) and signed free autographs for hundreds of fans at That's Entertainment in Worcester, Massachusetts. The event was part of Trailer's official "50th Anniversary of Boomtown" celebration tour. Then Worcester Mayor Tim Murray officially proclaimed it "Rex Trailer's Boomtown Day" throughout the city to mark the occasion, and Worcester City Councilor Frederick C. Rushton read the proclamation to the crowd.
In 2011, Trailer donated his three .45-caliber revolvers with staghorn handles to the Massachusetts State Police Museum in Grafton, Massachusetts. Just prior, the gun shop where Trailer was storing them had gone out of business. The guns very nearly went on the auction block before Trailer and Michael Bavaro learned of the situation and retook possession.
On September 11, 2011, Trailer appeared at That's Entertainment in Fitchburg, Massachusetts, to meet fans, sing songs and sign free autographs as he marked the 55th anniversary of Boomtown. The appearance coincided with the tenth anniversary of the September 11 attacks, and Trailer sang a song he had written to honor the victims of 9/11, "I Appreciate You". He had first performed this song on 2002/09/10 at the Comedy Connection in Faneuil Hall. He explained the song's significance before that earlier event: "Ever since 9-11, the world has changed for all of us. We have to stick together, protect each other, and let those you love, respect, and admire know how much you appreciate them."
On December 18, 2011, Trailer wrapped up his 55th Anniversary Tour in Waltham, Massachusetts, at Café on the Common. Trailer debuted a long-lost Boomtown segment called “Pablo’s Used Cars,” which featured the physical comedy of Trailer’s beloved sidekick, Pablo (actor Richard Kilbride).
In 2012, Trailer continued to appear at events in towns all around Massachusetts. On September 15, 2012, Trailer was at the Ayer Town Hall, where a gathering of fans joined him for his 84th birthday celebration.
Rex Trailer