Donnie Wahlberg Leaves a $2,020 Tip for Server at Massachusetts Restaurant: 'Her Jaw Dropped,' Says Owner

New Kids on the Block and Blue Bloods star surprised the staff at Marshland restaurant as part of the #2020TipChallenge.

Photo: John Sciulli/Getty

Donnie Wahlberg continues to spread the love—and money—this year.

On Saturday, Nov. 7, the Blue Bloods star dined at a Marshland restaurant location in Plymouth, Mass. and left his server, Denise Andrews, a $2,020 tip on a $35.27 bill.

"A very special thank you to our friend @donniewahlberg! When asked about it all he said was 'who’s up next?!'" the restaurant wrote on Instagram on Wednesday. They also posted a photo of Wahlberg's receipt, which included the Boston native's handwritten tip, signature and the #2020tipchallenge hashtag.

"Donnie has been here before in the past and he always asks for [Denise]," Marshland restaurant owner Marty Finch, 56, tells PEOPLE. "He had his normal order: steak tips with some grilled asparagus and some poached eggs. She always knows what he wants."

Andrews may have known the New Kids on the Block star's regular order, but she was not expecting what came next. "When he left he just said, ‘Denise, you’re all set. The payment is on the table,'" Finch says. "She always says he’s a very good tipper anyway but her jaw dropped, to say the least, when she saw that amount of tip."

The surprise tip lifted the staff's spirits, says Finch, who also runs two other nearby locations of the restaurant. He says Andrews, who has worked at Marshland for eight years, was quick to share the money with her coworkers. "Denise was very generous. She tipped out her fellow waitstaff and the guys in the kitchen, and she actually donated too," he says. "She’s working on getting two families turkey meals during the holidays, so she’s generous herself. Donnie said to pass it on, to keep this positive stuff going, so she’s trying to do that as well."

The year has been a tough one for many independent restaurants and small businesses as they face unprecedented financial stress during the COVID-19 pandemic—and Marshland is no exception.

"Me, as the owner, we’ve struggled these last eight months. We’ve really tried to keep these doors open," says Finch. "We actually closed for a couple of months because it just wasn’t looking good. But we reopened, and it’s been a blessing that we did. We’re kind of like a homecooked-food-neighborhood-type restaurant, so it’s just been a really good feeling all around."

He adds about Wahlberg's generosity: "It was just very uplifting for everyone."

The “2020 Tip Challenge” is a reference to a tipping trend that started in January 2020 in Michigan, when a server at Thunder Bay River Restaurant received a $2,020 tip on a $23 bill. On Jan. 2, Wahlberg and his wife, The Masked Singer host Jenny McCarthy, also left a $2,020 tip for an IHOP server in their hometown of St. Charles, Ill.

A few days later on Jan. 5, Harry Styles—who was on vacation at the time in Anguilla with longtime pal James Corden and Adele—left his own $2,020 tip on a $472.50 bill after a group dinner.

“@donniewahlberg you got the second worldwide response from Harry Styles all the way from St Thomas Virgin Islands with @j_corden and @adele,” Styles' server in Anguilla wrote at the time, referring to Wahlberg's IHOP tip.

“I just started crying. I couldn’t believe it. I mean, who does that? It was a blessing,” Bethenny Provencher, the IHOP server who received the tip, told PEOPLE at the time. “I just moved into an apartment, I’m a single mother—by myself with my son. So I struggle every day to make ends meet. And now I can buy furniture and put some money in the bank, and make sure my son is good.”

Wahlberg has been surprising restaurant employees with hefty tips long before the 2020 Tip Challenge began. In 2017, the singer left $500 for Waffle House employees working the night shift in Maryland, and also gifted a $2,000 tip (and front row concert tickets and backstage passes) for Waffle House servers in Charlotte, N.C.

Additional reporting by Mary Honkus