Winter can turn Boston’s City Hall Plaza into a lonely tundra, a wind-whipped expanse to be crossed as quickly as possible. This past December threatened to be no different, as a chill settled over the region just as the holiday festival known as Boston Winter returned for its second year.

Instead, the plaza has pulsed with activity, drawing bustling crowds to an outdoor shopping plaza, ice skating loop, and a wine and beer tent.

One recent afternoon, teenagers from Phillips Academy came for a skating date; a couple from Belmont celebrated their third dating anniversary with a beer in the heated tent; a retired couple from Plymouth checked out the shops.

“It’s working,’’ said Ed Hilton of Boston, perusing an artist’s drawings of Fenway Park and the Boston Common with his adult daughter, Heather.

After a mediocre debut last year, the fair has drawn more than 300,000 people since opening Nov. 24, easily surpassing last year’s total. Organizers expect more than 500,000 visitors by the time the market closes at year’s end.

About 80 vendors — twice as many as last year — have set up shop, and the number of skaters is on pace to double.

The company behind Boston Winter, Boston Garden Development Corp., said the improved turnout has been heartening. The company is a subsidiary of Delaware North, which owns and operates TD Garden, and signed a three-year contract with the city to manage the event.

Tricia McCorkle, a spokeswoman for the development group, said the winter fair is emerging as a “new holiday tradition’’ in Boston. Patrick Brophy, the city’s chief of operations, said the event is bringing new life to the plaza.

“There’s definitely a desire to do this’’ in the future, he said.

Expectations could have been far bleaker. Organizers reported $1.2 million in operating losses in the event’s debut, mainly because of first-year setup and planning expenses. The city received $175,000 for hosting the event.

Staging the event on the long-lamented plaza has not been easy, and city officials are taking note as they look to rebuild the area to accommodate similar events. Vendors have quietly grumbled about this year’s design, from the walking traffic flow to the location of concession stands and temporary bathrooms — all dictated by the plaza’s infrastructure.

The city has mapped out new plans for the plaza, which includes laying new walkways, shoring up the plaza’s foundation, and planting new trees. Officials are now seeking bids for the project, which could cost more than $80 million.

Brophy said that the city’s vision for the plaza has been shaped by the performance of events like Boston Winter.

“I think we all recognized there would be a challenge,’’ he said. “But being able to demonstrate you can activate such a large space that has literally been dormant for decades is something that speaks to the creativity of [Boston Garden], and the creativity of the city.’’

The plaza is built atop subway tunnels, and its ability to handle infrastructure — from electricity and water to computer data — is limited. That has forced organizers to scrap a range of ideas, including a Ferris wheel, light shows, and a larger beer garden.

Organizers invested more in infrastructure this year, McCorkle said. So while they expect revenues to increase from last year, they do not expect to turn a profit.

But as “the city implements the long-term strategy to ‘rethink City Hall,’ and make the needed investments in the plaza, we hope for a continued partnership that will unlock the full potential for the space,’’ she said.

Mike Ross, a former city councilor and lawyer who has lobbied for improvements to the plaza, said the winter festival — and the future of the area itself — are at a pivotal time.

“A winter market has great international relevance, and is an important cultural event for any city, with places to gather, shop, eat, or just hang out,’’ he said. “I think it’s very impressive what they’ve been able to do, without any infrastructure. But to do it right, they really need to bring in some infrastructure so that it can be bigger and more successful.’’

One recent afternoon, several visitors took advantage of warmer weather to explore the festival, including the teenaged couple from Phillips Academy. They had thought about going to the Frog Pond skating rink, but chose the plaza instead.

“This was the main attraction,’’ Cecelia Chen, 18, said of the skating loop.

Al and Mary Tousignant, retirees from Plymouth, had heard of the festival and wanted to see it for the first time; they say it has the potential of New York City’s Bryant Park winter festival.

“They needed to do something down here, with all the brick,’’ Mary Tousignant said.

Michael Renteria, 32, and Emily Shannon, 31, came from Belmont to celebrate their third dating anniversary and said the event was festive and family friendly. They felt a bit like tourists in their own city, Shannon said.

“A project like this, you have to give it room to grow,’’ she said.

Milton J. Valencia can be reached at milton.valencia@globe.com.