What started with a Worcester police officer and his wife spending $1,000 of their own money on candy has grown into a Halloween tradition that now draws thousands of children to Union Hill. Hill-O-Ween returns to 121 Providence St. from 5 to 8 p.m. on Saturday, marking its 12th year as what organizers describe as a city-wide celebration that began as a small neighborhood safety effort.
From a Personal Candy Run to a City Tradition
The idea traces back to Worcester Police Officer Sean Lovely, who wanted to create a safe trick-or-treat event for children in the city's Union Hill neighborhood, according to MassLive. Lovely has said he wanted to concentrate children in an area that was accessible for parents and safer for trick-or-treating, and he and his wife bought roughly $1,000 worth of candy to get the effort off the ground, per the same report. Lovely and his collaborators settled on a name for the gathering: Hill-O-Ween.
The event has deep roots in Worcester's Union Hill, where what was then called Union-Hill-o-Ween held its second annual celebration back in 2016, according to the Telegram & Gazette. That early version took place at a trick-or-treat circle off Providence Street near Morse Field and featured music, face painting and a costume parade, the paper reported at the time.
Growth Has Been Dramatic Over the Years
Hill-O-Ween's candy distribution has expanded from 12 tables to 85 tables, per MassLive's reporting, a physical measure of just how much the event has grown since its early days. The event now draws thousands of children, with Worcester police telling Patch that it pulled in more than 4,000 kids the year prior. By 2021, Lovely was collecting about $10,000 worth of candy and expecting roughly 5,000 children from the neighborhood and beyond to show up, according to Spectrum News 1, which also noted that dozens of people donate candy each year to help make the event possible.
The celebration wasn't without interruption. Spectrum News 1 reported that Hill-O-Ween was canceled the year before its 2021 return because of the COVID-19 pandemic, and Worcester police helped direct traffic once it resumed. Accounts of the event's exact age have varied in local coverage — Patch reported the event had been held for the past 10 years, while the Telegram & Gazette described 2025 as its 11th year — but organizers now count this year as the 12th annual Hill-O-Ween.
A Partnership Spanning Police, School and Charity
Hill-O-Ween is a collaboration between the Worcester Police Department, Worcester Academy and St. John's Food for the Poor, according to MassLive. Worcester Academy allows its school grounds to be used for the event, while the St. John's Food for the Poor program provides food and groceries to attendees in need. Patch similarly described the gathering as a partnership between the police department, Saint John's Food for the Poor and Worcester Academy aimed at giving children in the Union Hill, Grafton Hill and Vernon Hill neighborhoods a safe way to celebrate Halloween.
Jamie Sullivan works with Lovely to bring the event to life each year, per MassLive's reporting. Community groups have become fixtures of the celebration too — the Irish Club sets up a table at the event every year, and the Italian Heritage Parade Committee is set to attend this year's gathering. Worcester 311 will also have a table at Hill-O-Ween to help people sign up for city notifications, a role identified by Worcester Police Sgt. Elise Miranda.
Touch-a-Truck and a Longtime Volunteer Base
This year's event will include a touch-a-truck activity alongside the usual trick-or-treating, organizers told MassLive. The celebration continues to lean on volunteers, including parents who first attended Hill-O-Ween with their own children years ago and have stuck around to help run it.
Paul Saucier, who grew up in Worcester's Union Hill neighborhood, said Hill-O-Ween offers children a safe, organized place to celebrate with friends, according to MassLive. Saucier credited the event's growth to Lovely and his partnership with Sullivan at Worcester Academy, and described Hill-O-Ween as an example of community policing that connects officers with kids. Lovely, a 25-year veteran of the Worcester Police Department per the Worcester County District Attorney's Office, has even said the event is trying to compete with Salem, according to MassLive's reporting. Worcester police officers handed out candy at Hill-O-Ween last year, and organizers expect another large turnout when the gates open Saturday at 121 Providence St.
