Oliver Plunkett Street in Cork, which celebrates its 300th anniversary this year, would appear to be the best street in Ireland. It's certainly the only Irish street shortlisted for this year's Great Street Award, run by London's Academy of Urbanism. Geoff Haslam, the lead assessor for the academy, said: "We have been overwhelmed by Oliver Plunkett Street today. It offers everything that we are looking for in a Great Street, and more. We sometimes have to search for the DNA of a street, but Oliver Plunkett Street exudes it: it's a vibrant, living street and community, full of little surprises and it is clearly on an upward trajectory."

It's a second street in a second city, a long, partially pedestrianised thoroughfare with shoppers, buskers, an Evening Echo seller ("Echooo" he calls), historic buildings such as the GPO (once the Theatre Royal) and 111 independent businesses.

Many of these businesses are in their third generation of business. Take MJ Galligan's Furnishing and Fabrics at No 132, run by 80-year-old Ann Galligan and her daughter Eleanor. Ann's father, Michael Joseph Galligan, first established a furniture business on the street in 1919, when it was still called George's Street.

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Ann beckons me into a back room. “Bring in the old kick-stool there, Eleanor, and I’ll put the cushion on it.”

This little room is filled with photographs of relatives, old pictures of Patrick Street, small religious statues of St Francis and St Anthony, and beautiful wood carvings of dragons and Celtic designs, made by her father to show pupils "different timbers and how they could be matched" (Michael also taught woodwork). Over the years the business moved from furniture to fabrics "because there was no son in the family", but "the old sawdust is in the blood", she says.

Ann joined the business on April Fool’s Day, 1951. In those days they were based at the top of No 16. “You climbed up 33 steps. It was like coming up to Aladdin’s cave. When they came up those stairs, they came up to buy. They didn’t come up 33 steps for a look.” She laughs. Now, “people come in because they’re waiting for the bus”.

She recalls businesses that were on the street then: a foundry, a provision shop, a tailor, a dance hall, a printing works. “But you can still get anything on this street,” she says, and she praises the spirit of neighbourliness. They moved to 132 in 1991, and her daughter Eleanor – then a nurse – started to help her out. “It was an answer to prayer,” she says.

Ann still comes into work every day? Well, her father worked right up until he died aged 75, she says. “I could stop at home, but sure I’d crack up.”

The street's identity as a distinct area has been nurtured by a new group called the Plunkett Quarter. Valerie Cahill, a self-described blow-in who's been on the street four years with Ikon Hair Design, explains where the idea came from. A few years ago, Clodagh Daly from Daly Opticians came in to get her hair done and told Cahill "about her vision for the place. I said 'please stop talking' and I came back with a PowerPoint presentation I had made up."

So, “with the country on its knees”, the two businesswomen held a public meeting to outline their ideas about how to market the area. To the sound of hairdryers, she talks about the resilience of the traders and the long histories of the businesses on the street. They have plans to put up arches entering the street and to hang flower baskets. “We started thinking Carnaby Street or something like that,” she says. “You immediately get a beautiful feeling when you come in there. We’re saying it’s the heart of the city, because it really is.”

Receipt from 1938

Peter Casey, who runs Casey's Furniture shop with his brother David, takes me through the deceptively large shop, which was founded by his grandfather John in 1921. He greets people as he goes, and we stop to look at old photographs along the way. There's one of a man with a horse and cart. "His two sons still work here and he's still in and out."

There’s a framed receipt from 1938 on another wall. What’s it for? Peter peers in to try to read it. He’s not sure. “The writing wasn’t so good in those days,” he says.

Upstairs he shows me the “rabbit warren” of attic rooms where the factory once was and points out several “Cork 11-bar chairs” made in the factory, now esteemed by antique collectors. He ponders why family businesses last so long on the street. “I wonder is it the beauty of being the second street?” he says. “The lure of big money passed everyone by.”

In a little anteroom of Keane's Jewellers, another business on its third generation, Pat Keane tells me how his parents set up in 1948 before expanding into the tea warehouses next door. He's seen the same people come for Communion gifts, wedding rings and, eventually, presents for their grandchildren. The seating areas are "for the faint-hearted", he jokes. "When they see the price they need to sit down and we bring them a whiskey."

Across the road in Saville Menswear, Jim and Pam O’Regan outline their own long history on the street. Jim’s father ran a provision business there. He was known as “the spice man”, says Jim, because he specialised in preparing the spices for the spiced beef at Christmas. “The street is like a relation to me,” he says.

Jim started the business in 1979 in what was once the Imperial Cinema. “We still get old lads who come in and say, ‘manys the good jag I had in the back of this place,’ ” he says.

Jim’s father ran “a people’s business”, and he and Pam strive to do the same. Shoppers regularly ask to leave their groceries behind the counter while they run to other shops. Jim’s father used to even mind babies for people, says Pam. “He’d put them in a wee crate.”

They laugh. “At that time the oranges would come in a timber box with all straw and everything, and he used to remove the oranges and put the child in it,” says Jim.

“He was a very gentle man,” says Pam.

The street is still a community, says Pam. Some days, she says, they can't get off the street because they keep bumping into people they know. The community spirit is particularly evident when the street floods. This is a historic problem. It happens whenever the Lee bursts its banks, most recently in February 2014. Everyone helps one another and gets on with it, says Pam. "A man was literally swimming down the street," she says (there's YouTube footage of this). "But at 11 the next day we sold our first suit."

Tom Dwyer also mentions the man swimming down the street. He has seen a few floods. He opened The Cobbler in 1980 when his family's shoe factory closed. He found the premises here, he says, "more by luck than good management". In the 1980s shoe repair was in great demand – "we hardly sold a tin of shoe polish in those days" – but in recent times business has expanded into key cutting and leather goods. He has customers who have been coming for years. "It's brilliant you're still here," they say. Cork people have a great affinity for the street, he says. "Thirty-five years here . . ." he says, and laughs. "You wouldn't get it for murder."

Marking Christmas annuals

The late Liam Ruiséal started selling books on Grand Parade in 1916 and moved to Oliver Plunkett Street in the 1920s. He was involved with the Gaelic League and the Irish Volunteers and was friends with Cork republican martyrs Tomás Mac Curtain and Terence MacSwiney. "He marched every Easter Sunday," says his granddaughter, Bríd Hughes, who now runs Liam Ruiséal's with her aunt, Sarah.

“We were born and bred here,” she says. “I remember my first job was marking the Christmas annuals and marking loads of them before hiding upstairs to read them.”

Liam was stern, she says, but very well-known and liked. People who knew him still come in and ask, “are you a Ruiséal?”

The Friday before the last flood, Michael Cronin of Cronin's Menswear came down to warn Bríd Hughes it was going to happen. He knows the signs (a complicated combination of high tides, low atmospheric pressure and southerly gales). "Two days before I was born, the mother was up in a ladder in the shop here due to flooding," says Cronin. "So I've been there before I was born and I've been there at every flood since."

Cronin's father first opened the shop in 1951, and Michael has been working here since the age of eight. His first shoes came from a well-known Cork character called Andy Gaw. "My father would give him cardboard boxes, which he'd sell up on Washington Street. When I was born he gave my parents a present of a pair of shoes for me as thanks."

He lists off businesses that have come and gone. The biggest change, he thinks, was pedestrianisation in the 1980s. “A lot of people loved coming here because you could walk around the street without traffic.”

Who shops here? Everyone, he says. “We get a lot of Germans buying hats.” On cue a German couple come to the counter to buy a hat. “That’s guaranteed to keep the rain from your head,” says Cronin.

All the shops work well together, he says. There was a sale in Casey’s the week we meet and a lot of the people who come into town for the sale drop into Cronin’s. “It’s a special street,” he says. “Sometimes I sit in the office upstairs with the window open and listen to the hum of it. It’s like being on the beach and hearing the waves. The hum of this street, there’s something magical about it.”

• The winner of the Great Street Award will be announced in London on November 6th academyofurbanism.org.uk