Eddie Montgomery also gives an update on how Troy Montgomery's family is doing since that tragic day

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Last Friday, Eddie Montgomery returned to Nashville’s iconic Grand Ole Opry for the first time since the funeral for his longtime musical partner Troy Gentry in September. “It was very, very emotional. We had a bunch of family and friends there,” he tells PEOPLE Now. He arrived at the venue early to have a personal moment of reflection. “I had to let some emotions out and walk around a bit. I feel he was with me.”

Montgomery, 54, is in the midst of a tour to support Montgomery Gentry’s Here’s to You, the album wrapped just two days before Gentry’s shocking death in a helicopter crash on Sept. 8 at age 50. Since then, Montgomery has made a valiant effort to pick up the pieces — as have Gentry’s widow, Angie, and teenage daughter Kaylee. “They’re doing their best,” says Montgomery. “[Kaylee] lost a father and Angie lost her best friend. I know how it’s been in my heart; I can only imagine being in their position.”

RELATED VIDEO: Eddie Montgomery on His CMAs Tribute to Troy Gentry: ‘I Wasn’t Sure [If] I Could Do It’

Mother and daughter made an appearance on the red carpet at the 2017 CMA Awards in November, where Montgomery delivered a surprise tribute to his fallen friend and collaborator by performing their hit “My Town” alongside fellow country titans Dierks Bentley and Rascal Flatts.

“I wasn’t sure if whether I could do it or not,” he recalls of the moment. “If I’d had to do ‘My Town’ all by myself, I wasn’t sure if I could get through it.” The moment he stepped into the wings, he saw Gentry’s beaming smile projected onto the stage display. “That’s when the lump got in my throat and my heart dropped a little bit. [It felt like] he just shooed me out there and said, ‘Go do it!'”

Five months on, the sound of his partner’s voice still brings to mind happy, if poignant, memories. “He loved life. He loved his kids, he loved his wife. He loved everybody,” says Montgomery, who takes delight in recalling his more mischievous side. “There was no telling what he was gonna say to you. He always kept this big wooden spoon with him out on the road because he loved to stir stuff up. He was always pulling pranks.”

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Montgomery Gentry in 2014.
| Credit: Kristin Barlowe

More than a source of comfort, Gentry’s zeal provides strength for Montgomery to push forward in his new role as a solo artist. “Life is short, we’re gonna live every second of it,” he says of their unspoken credo. “I suggest to everybody else: if you got a dream, go get it.”