Fiddler's Green celebrates 20 years in Winter Park

Fiddler's Green hits two decades

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  • | 9:00 a.m. November 24, 2016
Photo by: Sarah Wilson - Fiddler's Green proprietor Donal O'Brien raises a glass inside the Winter Park pub's front dining room.
Photo by: Sarah Wilson - Fiddler's Green proprietor Donal O'Brien raises a glass inside the Winter Park pub's front dining room.
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Fiddler’s Green can be defined by many things. Its perfected pour of Guinness. Its fried and flaky fish and chips. The local bands that grace its stage most days of the week.

But owner Donal O’Brien said it’s the people – both its customers and staff – who have defined the pub’s 20-year existence.

“We don’t want everyone to be the same here,” he said. “Everyone has their own quirkiness… There’s so many different characters.”

At the bar, there’s the businessman who drives a half-hour from his office in Winter Garden nearly every day after work to hang out after a long day. And the lead singer of a local cover band who stops by for a lunchtime bite and beer.

O’Brien said he often sees people who make millions and people who are just barely making it sitting side-by-side at the bar having a chat.

“It’s just nice to find people to share things with,” he said. “You never know who you’re talking to.”

There are no TVs in most of the pub’s rooms. O’Brien said that was intentional to encourage people to take a step away from the screens.

“I love when I just see groups of people just sitting around talking and laughing,” he said. “…It’s always interesting. We always have great conversations here.”

Behind the bar and at the hostess stand are workers who started when the restaurant first opened – 20 years ago last month. Manager GiGi started as a server and worked her way up. Now her daughter, who O’Brien said he has watched grow up, is on staff waiting tables. Rob Ross, the main man behind the bar, started tending the taps four years ago, and said he hasn’t felt liked he’s worked a day since.

“I don’t feel like I’m going into work; I feel like I’m going to hang out with friends,” Ross said. “…It’s like family. I feel like I’m coming home to my family.”

O’Brien, an accountant by trade, never imagined he’d be running a restaurant. He thought maybe he’d be helping run the Winter Park Fiddler’s Green location for five years tops. Fifteen years later, he’s still at it. The pub offers him a literal taste of home, after he emigrated from Ireland at age 30.

The Guinness at Fiddler’s, he said, is poured just as good as one you’d get across the pond. And he’s had employees take trips over to The Emerald Isle and come back insisting that despite their best efforts, they couldn’t find better fish and chips than the ones they sell here in Winter Park.

“It keeps me in touch with home,” O’Brien said.

After two decades of trips coming back and forth from his current home in Ft. Lauderdale to keep tabs on Fiddler’s, O’Brien said he’s now finally looking to relocate permanently to Winter Park.

Over the last 20 years, he and his pub have become staples in the city of culture and heritage’s community. Next March, Fiddler’s will host its ninth annual 5K raising money for Habitat for Humanity of Winter Park-Maitland and the Conductive Education Center of Orlando. In total, the race has banked more than $150,000 for the charities since its inception. The pub also sponsors the annual Winter Park St. Patrick’s Day Parade, which has turned the city green for 37 straight years as the only St. Patrick’s Day Parade in Central Florida.

For its service to the community, in April of this year, Fiddler’s was given an award of recognition by the city of Winter Park.

O’Brien said the pub’s work in the community is an extension of the welcoming warmth he hopes keeps drawing people into Fiddler’s for a pint.

“If people walk in the door and feel a warmth, it’s very important to us,” he said.

“People who walk in the door can go get a drink anywhere… We want to give them a reason to come back.”


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