Overlooking one of the few roads running through Sandy Hook, Ky., is a statue.

Perched adjacent to a cemetery, the monument pays tribute to a man whose music began in the tiny town of 600 people but eventually reached around the world.

Keith Whitley recorded 19 songs that made the Billboard country charts, including five straight number one hits in the late 1980s.

Monday was the 27th anniversary of Whitley's death.

He died May 9, 1989, at the age of 33, cutting short a career that, at the time, seemed destined for so much more musical greatness than he had already experienced.

But Keith Whitley was more than a sentimental songwriter with a golden voice. He was a proud Eastern Kentuckian.

And the legacy he left behind in his hometown of Sandy Hook is more powerful today than it's ever been.

Anyone looking for evidence of that can find it at the Frosty Freeze - a restaurant Whitley used to enjoy frequently and where, to this day, some of his memorabilia is displayed.

"As long as I am in here, they will be up," Frosty Freeze owner Judy Pennington says when pointing to the Keith Whitley posters and flyers on the walls of the restaurant.

Pennington and her husband, Percy, are longtime owners of the Frosty Freeze.

Walking inside the store is almost like traveling back to a time before Whitley was a country music sensation and was simply "Keith" to those who knew him.

Judy Pennington recalls Whitley dating her sister, always carrying his guitar and wearing "pointed-toe shoes."

Whitley's music and memory stay alive, thanks, in part, to an annual concert in Sandy Hook organized by the nonprofit "Friends of Keith Whitley."

This past Saturday marked the third year for the concerts, which started in 2014 on the 25th anniversary of Whitley's death.

His brother, Dwight - an accomplished bluegrass and country musician - marvels at the number of people who come out to support Keith and his music all these years later.

"Oh, they're still mourning over Keith," Dwight Whitley said. "They lost their hero. I mean, they're honoring him all the time."

"Sandy Hook never forgot Keith. And I'll say this, Keith never forgot Sandy Hook."

And now there's another monument by which to remember him.

Bluegrass musician Scott Napier and artist Michael Young - both avid Keith Whitley fans - worked together to make a new sign welcoing people to Sandy Hook.

The sign is hand-painted by Young with Whitley's image displayed prominently on it.

Napier transported the sign from Hazard to Sandy Hook Saturday for the concert, where it was unveiled to the crowd and later installed next to Route 7.

"We can't tell Keith personally," Napier said. "He never got to see the impact. It's just my way to show somebody how he loved Sandy Hook. He always talked about Sandy Hook from the stage. He thanked the people of Sandy Hook, so this is me thanking the people of Sandy Hook and Keith and his family."

Family always had a broad definition to Keith Whitley.

No one knows that better than Judy Pennington from the Frosty Freeze.

That's because Pennington's only child, Courtney Seth Pennington, is buried next to Whitley's statue.

Courtney died in October when his truck crashed coming back from Big Blue Madness. He was 32.

When Courtney Pennington was a boy, Keith Whitley once asked him to take the stage and play with the band. And he did.

Now Pennington rests in peace right next to the statue of the country music icon he admired more than anyone.

Judy Pennington believes her son and Keith Whitley are playing music together in heaven.

"From the bottom of my heart, I know it," she said. "Every time I go to that cemetery I tell them both to keep on playing the music. Stay together. That's what I tell them every time I go."

During Saturday's concert, Judy Pennington took the stage just like her son. In his memory she presented a check to Friends of Keith Whitley that will help provide college scholarships to kids who plan on pursuing careers in music.

It's something that rescued her from overwhelming grief.

"I didn't even speak to people," Pennington says of the days after the crash. "No disrespect, I couldn't. Well all at once this has come up. It's brought me out of it. It has actually brought me out of it."

Nearly 30 years after his death, Keith Whitley is still lifting people up.

His music remains timeless when time for some seems to run out too soon.

But one thing that will never run out is the pride Sandy Hook and all of Eastern Kentucky feels for the man who was no stranger to the rain.