Smithtown residents salute retiring UPS driver Gregory Watkins Sr. who delivered packages (and hope) amid pandemic

Late Thursday afternoon, Gregory Watkins Sr., perhaps the most famous UPS driver in America, delivered the last package of his career and then parked his big brown package car on a leafy Smithtown street. 

Longtime customers, fellow drivers and his some of his family waited with balloons and cards on Mark Drive to celebrate his retirement after almost 34 years.

“Goodness,” Watkins said, and began hugging people.

“Congratulations, Bud. Enjoy it,” said one man. 

Watkins’ celebrity dates to the pandemic lockdown in 2020, when dozens of homebound customers, grateful for his work, threw him an impromptu parade. Video of the affair — with Smithtown residents chanting “Greg! Greg!,” waving signs and handing him a giant potted plant — was viewed millions of times on social media and on national network news. 

“Our one tie that everyone had was Greg,” said Linda Muratore, a speech pathologist in South Huntington schools who helped organize the tribute that day. “He was the one person that everyone saw, and he was working so hard … He was our connection to normalcy.” 

Watkins, 59, of Coram, spent the last 17 years of his job on a Smithtown route that covered Route 111 and residential neighborhoods to the south of Main Street.

He made more than 1 million stops, delivered more than 6 million packages and drove 900,000 miles, according to UPS.

When he started the job, Watkins recalled during an interview on his last lunch break, he had anxious dreams where he was rushing to make deliveries. By the time of the pandemic, he was a seasoned pro delivering 400 packages a day, a third more than normal, even if it sometimes took him 12 hours. 

 “In a time when we were masked and gloved up, people weren’t leaving their homes,” Watkins said. “People now found themselves having to trust the internet to get their products."  

He recalled days of sometimes delivering "20 to 30 packages from BJs, Costco" to a single home because people no longer shopped in person. 

Many customers said they cherished their quick front walkway conversations with the UPS man.

“Like a ray of hope coming to the door,” said Amy Fortunato, 63, a retired pastor.

Smithtown, population 116,000, “is not a small town, so when you do have that intimate ‘Hello, how are you doing,’ when it’s authentic — it makes your day,” added Fortunato’s neighbor Kristi Eikenes, 62, who works at a sleep disorders center.

Over the years, customers learned that Watkins is a competitive runner, that he loves fishing, and about some of the important people in his life: his wife, Katrina, 58, and their sons, Gregory Jr., Kyle, Garrett and Kharlin.

Watkins surely surprised some customers by sharing that his mother, then known as Maxine Herbert, sang in a rhythm and blues group, The Jelly Beans, that scored Billboard hits in the 1960s, and that he gave up his own dream of a singing career when he and Katrina started their family — opting instead for the dependability of a union job with UPS. 

Watkins' customers also shared with him: He knew whose parents were getting on in years, whose son-in-law was starting out at UPS, whose kids were graduating. He cherished those conversations too.

 “I’ve gotten to know a lot of people," Watkins said. "I’m going to miss that part of the job. I like what I do.”  

The UPS driver told the crowd on Mark Drive the prospect of retirement was bittersweet.

“Each and every one of you made my life so much better,” he said.