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When did Boston get so fun?

Counting the ways that our old-time city is finally starting to loosen up for young professionals.

Nicholas Little

Henry Guttmann/Getty Images

“I wanted to free the Boston audience from the chains that bound them,” American dancer Isadora Duncan after a scandalous 1922 visit to Boston.

IT’S A HOT SATURDAY AFTERNOON IN SOUTHIE, and a few of the revelers on a once-barren stretch of D Street are tossing a football around, beers in hand. Others are swaying lazily in swings that look like giant earrings. There’s table tennis and cornhole and a set of giant Jenga blocks. Everyone here is 27 years old. Even the babies.

In a once-forgotten part of a city with a reputation for stuffiness that predates even the existence of the country whose creation it kick-started — a city that once outlawed the celebration of Christmas — the Lawn on D exists for one reason and one reason only: fun.

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On the other side of Fort Point Channel a mile and a half away, the Rose Fitzgerald Kennedy Greenway is packed with people lying in hammocks, kids splashing in fountains, and street performers back flipping around the sidewalks. Not so long ago, as a surprisingly small number of the twentysomethings lined up at the food trucks here realize, this was the filthy, scary underside of an elevated highway. Even if you don’t like food trucks as much as the average millennial — if I brought you a chicken sandwich I cooked in my car, would you eat it? — this is progress.

And outside America’s most menacing City Hall, a little patch of artificial turf and a few dozen lawn chairs are spread out like some kind of ironic, whimsical welcome mat. OK, so the combination of direct sunlight, constant street noise, and vigorous government security doesn’t make for much actual fun. And within a month of its July debut, the turf is so trampled that you could see the outline of each individual brick through the thin green material. But you have to start somewhere, and, anyway, the addition to the wasteland surrounding City Hall is more emblematic than it is exciting. All of a sudden, examples of Boston’s efforts to shed its priggish reputation and let down its powdered wig are everywhere.

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On weekends, the T runs until 2 a.m. Sunday liquor sales start at 10 a.m. A casino seems to be coming to town. Thousands of people show up to roller skate and listen to Donna Summer at City Hall Plaza.

This certainly isn’t the Boston we’d all come to know and tolerate. How in the world did this city get so fun?

WHEN THE FAMED AMERICAN DANCER Isadora Duncan visited Boston, her risque number — involving a red scarf and little else — scandalized the stuffy audience: “Isadora Doffs So Much Staid Boston Gasps,” said a Chicago Daily Tribuneheadline.

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“I wanted to free the Boston audience from the chains that bound them,” Duncan said after the show. “I saw them before me shackled with a thousand links of custom and environment.”

That was in 1922, but in the minds of many, it pretty accurately describes last Thursday. Boston’s reputation has more to do with history and higher learning than it does with free-spirited fun.

Keith Bedford/Globe staff

Visitors relax in lawn chairs on City Hall Plaza, part of an effort to make the public space more appealing.

To be fair, Boston has always been a blast for those who know where to look. We’ve done wholesome pretty well — the Charles River Esplanade is packed whenever the weather is decent. The New England Aquarium and the Boston Children’s Museum have long been top-notch. And for tastes somewhere south of PG-13, the Scollay Square of a century ago hosted burlesque shows and vaudeville acts that brought in the college kids who have always kept Boston young in spite of itself. Once the city paved that over and built Government Center on the seedy rubble, the Combat Zone on and around Washington Street picked up the strippers-and-booze slack.

But even the fun stuff wasn’t always fun: The pre-2004 Red Sox spent the better part of a century developing new and innovative ways to ruin a day at the ballpark. The whole state has a ban on happy hour that was enacted in 1984, though it’s so fitting for us it feels as if it’s been around forever.

Long after cities around the country began jostling for position in the mental rankings of millennials who were talented enough to work wherever they chose, Boston is beginning to realize something that doesn’t exactly qualify as revolutionary: “Fun is important,” says Malia Lazu, whose Future Boston Alliance counts making the city more fun for young adults as one of its core goals. “You forget that when you live in Boston for too long, and people sort of look down on fun.”

In recent years, that was embodied by the administration of Mayor Tom Menino, who, for all his skill as a politician, was not one to cater to the appetites of the city’s young adults. But the image of Boston as not merely stuffy but intentionally square has roots far deeper than that. The 17th-century Puritan ban on Christmas celebrations lasted only 20 years or so, but the notion of, you know, enjoying the holiday didn’t really catch on for another two centuries. In some ways, Boston never stopped being staid.

“It’s been that way for so long,” says Lazu. She describes the city’s longstanding aversion to fun as something ingrained at the cellular level, kind of the way a flatworm can learn its way through a maze by eating another flatworm that had already figured it out. “It is part of the reason why we lose talent,” she says. “People want to feel at home. People want to feel welcome. People want to have pride. People want to feel a sense of connection. And if they don’t have that, then there’s no reason for them to stay.”

Dina Rudick/Globe Staff/File 2014

Southie’s Lawn on D attracts young and old.

But all of a sudden, evidence is everywhere that the city and its surroundings are open to the idea of having a good time. The Lawn on D isn’t perfect. It has an authenticity problem, Lazu points out — it’s in a neighborhood that not so long ago was a deeply uncomfortable place for people of color, and the crowds are overwhelmingly white in a city that isn’t. It’s also potentially temporary, with the threat of development in the area and yet more condos looming. But Boston has always been open for business. Finally, maybe, it’s open for fun.

FOR HER FIRST VISIT TO BOSTON, 25-year-old Noelle Peterson prepared a list of all the things she wanted to do: Faneuil Hall, the North End, a Duck Tour, Fenway Park — pretty standard stuff. But these things are tourist-grade fun, and anyone who has ever been a tourist knows that tourist fun is not actually fun. Her 24-year-old boyfriend, Joe Dooley, who recently moved back to Boston for a job after a year in Milwaukee, was on a somewhat different mission: Find some great new haunts. Friends in town recommended the Lawn on D, so the couple checked it out on a recent Sunday.

“It was pretty cool, because they had live music playing. You could get drinks,” Dooley says as they sit with a 23-year-old friend who recently relocated to Boston from Milwaukee, Chris Deanes.

“I’m still trying to get my feet wet and see what the city has to offer,” Deanes says. “But so far I really like it.”

For Boston, impressing the twentysomething demographic means playing catch-up. In Chicago, where Deanes grew up, last call can come as late as 5 a.m. (in Boston, bars can’t stay open past 2 — and if you want to catch the last train home most nights, you’d better settle up by midnight). Chicago’s Millennium Park, conceived in 1997 and opened in 2004, is practically as integral to the city as the Common is to Boston (and if 1997 sounds recent to you, consider that Deanes was about 5 years old). In fact, New York, Seattle, Omaha, the East and West Coast Portlands — they all have a bit of a jump on Boston. In Buffalo, of all places, on the grounds of an abandoned soap factory, Larkin Square is decked out with canopies and hula hoops and giant chairs and all manner of whimsical nonsense. Boston, meanwhile, has spent several decades relying on the home-field advantage of having thousands of college students trapped here for four or more years.

Aram Boghosian/File 2014

Boston has been experimenting with late-night MBTA service.

“If our competitive advantage is that we bring in the best talent from around the world, there’s no reason why we can’t create the ecosystem to keep them here,” says the 30-year-old Daniel Arrigg Koh, whom Mayor Martin J. Walsh lured back to Boston from New York City to be his chief of staff. “It’s actually something I talked to the mayor about during my interview.” Hired at age 29, Koh isn’t just a spokesman — he’s also a client. “I went to school in Boston and stayed for a year to work for Mayor Menino,” says the graduate of Harvard College and Harvard Business School. “I got a taste of what the New York City life was like, especially for young people.”

The biggest difference was in attitude, Koh says. New York welcomes new ideas about events or projects — citizens seek ways to make things work rather than finding reasons to shoot them down. Walsh, he says, was open to the notion that the city needed to lighten up and loosen its hold on the reins, and early evidence suggests he meant it. The late-night T experiment, which extended hours until about 2 a.m. on weekends, originated under Menino and got Walsh’s strong support. The longstanding cap on liquor licenses has been raised. City Hall Plaza hosts another installment of the wildly popular Boston Calling music festival this weekend. And the city, Koh says, is working to quash confounding regulations so entrenched that it’s not even clear where they came from, such as the city policy (it was apparently never actually a law) that said restaurants could serve alcohol to customers outdoors only if they were also ordering food.

Matthew J. Lee/Globe staff

Music fans pack City Hall Plaza in May for a Boston Calling show.

WHILE BOSTON HAS ALWAYS had a firm grip on the attention span of tourists, many of the city’s newest attractions appeal at least as much to those who live here but wouldn’t wedge themselves into Quincy Market’s glorified mall food court at gunpoint.

The new Boston Public Market is more food amusement park than grocery shopping experience, the space between its elegantly distressed exposed beams packed with artisanal this and boutique that. But unless tourists are inexplicably in the market for a pound and a half of frozen short ribs, this is primarily a destination for locals with impeccable credit ratings (if you want actual groceries, slightly worn vegetables are still available on Friday and Saturday under the tarps just outside).

The Greenway may not yet be what advocates once envisioned — an urban oasis to rival New York City’s gorgeous High Line — but it has turned into a success by any standard, supported both publicly and privately and abuzz on any given day with a diverse swath of the city’s population. The Wharf District Parks were complete on a recent Saturday with people napping in hammocks or taking selfies with public art. Large, intergenerational mobs were openly smoking weed on benches, which is a little brazen, but, hey: Fun is fun. Over their heads, a giant floating sculpture is strung between the office buildings.

Persuading young people who come to Boston for school or work to put down roots here has obvious benefits: Smart, engaged young people pay big civic dividends down the road. But those investments aren’t cheap. The Lawn on D costs the state convention center authority, which set the little park up last summer, about $2 million a year.

It’s hard at first to see how, without handing everyone who enters a crisp $20 bill, a 2.7-acre park could run up that kind of a tab. There’s maintenance, of course. Staff costs include security and workers at concession stands. And the park is fairly heavily programmed with concerts and events. In May, the Lawn on D was overtaken by the Pentalum, a giant, trippy, inflatable maze. Some events run a few bucks — the Pentalum experience was $5 — but that’s apparently not enough to offset the costs.

Pat Greenhouse/Globe Staff

The official opening of Boston Public Market on July 30.

Fun isn’t often a revenue-neutral proposition. The High Line is free to visit but relies heavily on a public broadcasting-esque “membership” model, rewarding donors with coffee mugs and magazine subscriptions and even Coach bags if they pony up enough. Even then, getting it off the ground cost the city more than $100 million. The boost to the surrounding neighborhoods was into the billions in private investment, according to former New York mayor Michael Bloomberg, but on a strict balance sheet analysis, it was a money loser. In that light, the Lawn on D’s $2 million annual budget, spent in service of the emerging Innovation District — monies that could potentially be offset by sponsorships — isn’t so hard to swallow.

“Some creative new things do take a little bit of time to connect,” says Kelley Gossett, a West Coast transplant who came to Boston to attend BC and Suffolk University Law School. She stayed to work as a policy advocate for nonprofits that combat homelessness and was one of the three young professionals behind No Boston Olympics, whose push against the city’s 2024 bid was grounded in the concept of opportunity cost — the idea that time and energy spent on the Games would be more valuable elsewhere.

Gossett, whose wish list for Boston includes a place to get a glass of wine on the Esplanade, says the city is due for a fresh look at some of its sacred cows. She says the questions Boston ought to be asking itself aren’t easy: “Is this useful for the city?” “Does this make sense for where we are now? Do we need to kind of rethink and reset for a new century?” Those questions are a lot harder than giant Jenga. But for now, finally, Boston isn’t telling all these kids to get off its lawn.

Nestor Ramos is a Globe staff writer. E-mail him at nestor.ramos@globe.com and follow him on Twitter @nestoraramos.

THE RESTAURANT BOOM BY THE NUMBERS

Nicholas Little

> 15,000 — Number of restaurants statewide, a 15 percent increase from 2002

> 200 — Approximate number of restaurants that opened citywide from September 2014 to September 2015

> 80 — Number of new liquor licenses to be issued in Boston 2014-2016

> 23 — Number of new businesses expected to open by the end of 2015 in and around Downtown Crossing

> 10 — Number that are restaurants

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