The Grapes, on Queen Street, has been sold by Admiral Taverns unlicensed and will not continue as a pub.
Former landlord Nick Herrington ran the pub for five and a half years with his partner Michelle.
He said: “When I came in The Grapes was shut and I rescued it and got it back up and running. It took me a while but the Filey people are friendly and customers became friends.
“It was just a good traditional local pub where people came in for a chat. A lot of people are upset because they like the traditional pub, you may come in a stranger but you leave as a friend."
Nick, who has previously run pubs in Scarborough and Bridlington, was told by Admiral that the pub was being listed for sale earlier this year.
He added: "I had no intentions of leaving. I thought it was going to be my retirement pub but Admiral have made that decision for me.
"It's a big shame, I'm totally gutted but all I can do is praise the customers that I've had over the years."
A spokesperson for Admiral said: “We can confirm that the sale of the Grapes in Filey completed in May and the decision to sell the pub was not connected to the impact of the Coronavirus pandemic.
"Following internal investigations we no longer believed the Grapes had a sustainable long term future and therefore took the decision to sell the pub.
"As a business we invest behind great licensees to help them run fantastic community locals.
"Last year we invested £175,000 in another pub in the area, the Station which has been a fantastic success so far and we are looking forward to reopening and welcoming our customers back when the time is right.”
Mr Herrington does not yet know his next move but doesn’t think he will stay in the pub trade.
"No pub will be The Grapes again," he said, "Every pub has it's own character and in a lot of them you don't get to know [the customers' personally like I did here."
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