The Staggies are aiming to win their first major trophy when they face Hibernian in Sunday's League Cup final.
"It's an area that went through the Clearances and had hardship in the past," MacGregor said of the Highlands.
"But today it is bright and energetic and [the club] represents something the community can believe in."
County joined the Scottish Football League in 1994 along with Highland rivals Inverness Caledonian Thistle.
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"The community wanted football at the highest level," MacGregor recalled.
"For both Highland clubs, we were denied that for so long so there's a passion for both clubs to do well.
"So to represent people in an area that's remote and hasn't a lot of people, and to be recognised throughout Europe now as being part of the football community of Scotland, is just, for me, a privilege, and also a statement that this area has got something to offer.
"I want people to be proud. I want the health centres to be empty on a Monday because people feel good about themselves and good about the football team."
MacGregor reveals that pre-match he likes to stand in the centre circle of every ground County visit in the top tier just to reaffirm that "my team is here".
"I do it every game because I can't believe that a small team from the Highlands is playing at the top level," he said.
"For me it is about a journey. It was me on the terrace as a 12-year-old boy at Victoria Park that gave me that bug.
"That's 50 years ago. People my age have seen the progression from the Highland League to the Premier League and to two cup finals, and for the five, six and seven-year-old boy it's the beginning of a journey.
"Can we get to Europe? Can we win something regularly? I'm not sure where it's going to end."
Describing County as existing "200 miles north of traditional football country", MacGregor says, should County beat Hibs and lift the League Cup, he would be "just pleased for the fans, the people of the Highlands".
And he added: "It's that sharing, people believing that they can be something in life and in sport, and that warm feeling that you'd take back here would make people feel better about themselves."
Ross County chairman Roy MacGregor views the Dingwall club's rise in Scottish football as emblematic of the talent that exists in the Highlands.