"It gets to the point at which people don't even fit on the sidewalks." A parent said that during public comment at the Hollis Select Board meeting of September 14, 2026, describing trick-or-treat night around Monument Square. She also pointed out the calendar. This year Halloween lands on a Saturday, "so it's going to be big."
Hollis covers a lot of ground, but on Halloween night most of the town ends up in a few blocks at its historic center. Each fix of the past few years has come from volunteers, a church, the library, or a group of parents adding a piece where the crowd got too big. On Saturday, October 31, those pieces fill the afternoon and evening, some in sequence and some side by side, and when you arrive decides which version of the evening you get.
The Crowd Has Been Growing for Years
The numbers start with the youngest kids. At that same September meeting, the parent said the Recreation-run Trunk-or-Treat drew 265 people in its first year and 343 last year. In November 2025, Hollis Brookline News reported that the second annual event drew hundreds of people and 15 decorated cars. The year before, the paper's preview noted, the first one had 12 cars.
The parent also said those totals undercount the night, since even more people arrive once the older kids head into the village after dark. According to Hollis Brookline News, the historic center "has become an increasingly popular Halloween destination," with Hollis Congregational Church, the Hollis Social Library, Town Hall, the Historical Society, Monument Square Market and many historic homes all taking part. In 2025 the library handed out candy from its front steps during the 6 to 8 p.m. window.
So the crowd has been building for several years, all aimed at one compact set of doorsteps.
Who Actually Runs the Night
The evening has no single organizer. At the September meeting, the Town Administrator said the Recreation Commission sponsors the earlier Trunk-or-Treat for small children at the library, and that the 6 to 8 p.m. trick-or-treat hours are "not really a Town-run event." A Select Board member added that the Recreation Commission had talked last year about taking over Halloween, but once the full-time position was voted down, the schedule had no room for it.
The fixes have come from elsewhere. Trunk-or-Treat spreads the youngest families into the afternoon. This year, Hollis Congregational Church is adding a limited number of community trick-or-treat stations on and near its patio, which gives the main event more places to hand out candy. Parents are working on the streets themselves. They applied for a special event license to close some roads around Monument Square, and the parent who spoke said they had raised enough to cover the police detail. She told the board she was not sure safety on the town's busiest trick-or-treat night "should be a parents/private citizen problem," and suggested there might someday be a committee.
Saturday, October 31, Hour by Hour
Put the pieces in order and the day falls into three windows, each meant for a different crowd.
| Time | What's happening | Where | Who it's for |
|---|---|---|---|
| 3:30 to 5 p.m. | Trunk-or-Treat, run by Recreation | Hollis Social Library parking lot | Ages 0 to 6 and older siblings; no registration required |
| 5:30 p.m. | Library lot opens for parking | Hollis Social Library | Station hosts and evening visitors |
| 6 to 8 p.m. | Town-wide trick-or-treating | Across town, busiest around Monument Square | Everyone |
| 6 to 8 p.m. | New community trick-or-treat stations | On or near the Hollis Congregational Church patio | Everyone |
The Trunk-or-Treat start time depends on where you look. The town's public notice and the Hollis Social Library calendar both say 3:30 p.m., while a community event listing says 3 p.m. The library is the host, so go by its 3:30 time.
The handoff between windows is the tight spot. Station hosts were told to use extra caution if they arrive before 5:30, because the little ones' event will still be wrapping up in that same lot. So if you have a preschooler and an older child, you can stay in the village for the whole afternoon and evening. If you only have older kids, arriving close to 6 p.m. lets you skip the overlap.
The Road Question Is Still Open
Closing the streets around Monument Square isn't up to the town alone. At the September 14 meeting, the Town Administrator said the special event license was still circulating among town departments, and that she wasn't sure a permit had been requested from the State, because the roads around Monument Square "are all State roads." The Select Board agenda for September 28 had no Halloween item. The town's trick-or-treat notice, posted October 8, gives the hours and the Trunk-or-Treat details and says nothing about closures, detours or parking.
Unless an announcement comes out before October 31, plan on Monument Square's roads staying open to traffic during trick-or-treat hours. That means sidewalks crowded with costumed kids next to working state roads. Bring reflective gear or a flashlight for the younger ones, keep groups together at crossings, and watch the town's notices page in case anything changes.
If Your Street Never Gets Trick-or-Treaters
Plenty of homes in Hollis sit on long, quiet roads where a bowl of candy by the door goes untouched. The church stations were set up partly for those households. The organizers specifically invited "families who live in areas of town that don't typically receive trick-or-treaters," along with local organizations, community groups and businesses. Spots are limited and you claim one through the organizers' sign-up page.
Hosts are asked to:
- Bring their own table, chairs, decorations, costumes and treats, plus a tent if they want one; non-candy treats are welcome
- Be set up and ready by 6 p.m.
- Keep decorations and costumes festive and family-friendly, since many young children will be there
- Plan for about 300 trick-or-treaters
- Clean up promptly when the evening ends at 8 p.m.
Logistics are spelled out too. Curbside unloading along Broad Street can help with supplies, the church won't open its restrooms, and a portable restroom will be nearby. Set the 300-trick-or-treater estimate next to last year's 343 Trunk-or-Treat attendees and you can see why hosts are told to bring plenty. That figure covered only the under-six afternoon crowd.
The Week Leading Up
The village calendar gets busy in the days before the 31st, with a few chances to get costumes, kids and yards ready:
- Saturday, October 24, 9 a.m. to 1 p.m. The Hollis Police Department holds a drug take-back, paper shredding and food drive at 9 Silver Lake Road.
- Saturday, October 24, 1:30 to 4:30 p.m. The Hollis Social Library runs a drop-in scarecrow craft made from craft tubes.
- Sunday, October 25, 2 to 4 p.m. The Hollis Conservation Commission leads a glossy buckthorn removal at the Flints Brook Trailhead, at the corner of Rideout and French Mill roads.
- Tuesday, October 27, 6 to 7:30 p.m., or Wednesday, October 28, 11 a.m. to 12:30 p.m. The library offers an adult wood-slice pumpkin craft.
If you have family or friends in the next town over, the Hollis Brookline News event calendar lists Brookline's own Trunk or Treat at 3 p.m. on October 31 in the RMMS parking lot at 22 Milford Street. It overlaps the start of Hollis's Trunk-or-Treat, so families who want to try both will have to choose.
At Purple Finch Properties, we've worked alongside Hollis families for years, and nights like this are a big part of why the town feels so close-knit. If Halloween has you thinking about your own house and what it's worth in this town, we're happy to talk it through. Get Your Free Home Valuation whenever you're ready, no pressure.