Holliston's Halloween runs five days, from Saturday, Oct. 24, through Wednesday, Oct. 28, and no single organization runs it. The library, the downtown shops, the SEPAC parents, Holliston Newcomers & Neighbors and the Holliston Historical Society each host their own event. Saturday morning is downtown, Saturday evening is on Woodland Street, Sunday morning is on the Rail Trail at Blair Square, and Wednesday night is in the barn. Apart from the downtown events on Saturday morning, no two hosts' events overlap, so if you follow the order the hosts set, you can get to all of it.
Saturday, Oct. 24, starts on Washington Street
The first event is the third annual Downtown Trick-o-Treat. The Holliston Public Library at 752 Washington Street lists its part as 9:30 a.m. to 2 p.m., with goodie bags handed out starting at 9:30. No registration is needed.
The shops on the street list longer hours than the library. The Bird & Bear Collective lists Downtown Trick-O-Treat from 10 a.m. to 4 p.m. on Oct. 24, 2026. Fiddle & Find is promoting a 10 a.m. start and says more details are coming. The two schedules seem to describe different things. The library's window covers its own goodie-bag stop, and the shops' window covers the wider downtown event. If you plan for both, the library's 2 p.m. end is the time to watch. Families who want a library bag should get there in the morning, and the shops will still be handing out candy after lunch.
There's also a quieter option at the library that morning. Reading Fur-iends runs from 10 to 11 a.m. in the Children's Room, where kids read aloud to Molly Bird. The library describes Molly as a rescue and certified therapy dog. This session doesn't need registration either. It runs during the trick-or-treat hours, so a child who gets tired of the crowds can sit and read to a dog, and the goodie-bag table is only a few rooms away.
Saturday evening moves to Woodland Street
Once downtown winds down, there's a gap of a few hours before the evening event on the other side of town. The town calendar lists the SEPAC Trunk or Treat for Oct. 24 from 6 to 8 p.m. in the Miller and Placentino school parking lots at 235 Woodland Street.
Here's how Saturday adds up:
- 9:30 a.m.: library goodie bags start at 752 Washington Street
- 10 a.m.: downtown shops start, and Reading Fur-iends begins in the Children's Room
- 2 p.m.: the library's listed window closes
- 4 p.m.: the downtown shops' listed window closes
- 6 to 8 p.m.: SEPAC Trunk or Treat at 235 Woodland Street
The two-hour gap between 4 and 6 p.m. is the only real break of the day, and it lands around dinnertime.
Where to eat between the stops
The places to eat are close to where the events happen. Dream Breakfast & Lunch is at 770 Washington Street, on the same block as the library, and its ordering page lists hours seven days a week. Grabbing breakfast before the 9:30 goodie bags doesn't mean moving the car.
Blue Moon Cafe is at 76 Railroad Street and serves bagels, baked goods, coffee and lunch, with posted daily hours. Railroad Street matters on Sunday, because Blair Square sits where Railroad Street meets Central Street.
For pumpkins, Out Post Farm at 300 Prentice Street has them, along with apple cider donuts, hot turkey dinners, pies and daily sandwiches. The farm says its Thanksgiving pre-orders opened Oct. 1. Its site doesn't list a cutoff date, so if you're already stopping for a pumpkin, check the online store then.
Bird & Bear has also brought in a newer name this year. On June 11, 2026, the collective held a ribbon cutting for Sifted with Love, an artisan micro-bakery started by Holliston resident Rebecca Caruso that makes cookies, cinnamon rolls and granola bars. If you're downtown on Saturday because of Bird & Bear, it's worth asking about the bakery.
Sunday, Oct. 25, the Rail Trail at Blair Square
On Sunday morning the events move to the trail. Holliston Newcomers & Neighbors holds its Great Pumpkin Trail Walk from 10 a.m. to noon, starting at Blair Square at Central and Railroad streets.
The walk is short. The group sets up games along the first part of the Holliston Rail Trail, as far as the first bridge, and gives out small prizes. It calls the walk an allergy-free way to celebrate fall, which is a real draw for families who skip candy-heavy events.
The cost is $6 per child, and adults are free. HNN accepts cash, checks and Venmo on the day, and it encourages adults to come in costume too.
The money doesn't stay with the walk. The proceeds go to the HNN Community Grant Fund. HNN lists recent grant recipients as the Parks & Recreation Summer Concerts, the Holliston Public Library's museum passes and the Holliston Police Department. So the walk on Sunday helps pay for the library that handed out goodie bags the day before. Questions about the event go to the contact on HNN's event page.
A Blue Moon coffee before the walk is just down Railroad Street from the start, and it gives you something warm to carry on the trail.
Wednesday, Oct. 28, ends in the barn
The last event is for grown-ups, and it has the most to do with history. The Holliston Historical Society holds The Golden Age of Silent Movies at 7 p.m. in its barn.
Pianist Richard Hughes will give a history of early film, with newsreels, cartoons, early comedy, historical drama, serial thrillers and slapstick. The program includes Harold Lloyd, Charlie Chaplin and Buster Keaton's chase scenes, all with narration and live music. Hughes will also show old sound-effect and animation devices, including a praxinoscope.
The Halloween part is the screening of "Habeas Corpus," a 1924 Laurel and Hardy short. The Society will serve hot apple cider and popcorn. It also suggests bringing a blanket, since the barn can be cold in late October.
The library and the Friends of the Library are co-presenting the program. That means the library is involved at both ends of the stretch, with goodie bags on Saturday morning and a share of the barn program on Wednesday night.
Who hosts which slot
Each host takes a different slot in the day or week and a different part of town:
- Library and downtown shops: Saturday morning and early afternoon on Washington Street
- SEPAC: Saturday evening at 235 Woodland Street
- Holliston Newcomers & Neighbors: Sunday morning on the Rail Trail at Blair Square
- Holliston Historical Society, with the library: Wednesday evening in the barn
The library is the link between them. It hands out goodie bags on Saturday, it's on HNN's list of grant recipients, and it co-presents the program in the barn on Wednesday.
The next stretch is already scheduled
The fall calendar keeps going after Halloween. WSK at 24 Water Street, in the Holliston Mill, lists a Trivia Night on Wednesday, Nov. 18, 2026, from 7 to 9 p.m., with small bites from The Daily Dish and drinks from The Black Harp.
Ten days later, Celebrate Holliston holds its 20th annual Holiday Stroll on Nov. 28, 2026. Trolley stops include Willow Brook Farm, the Holliston Historical Society, the Holiday Market at Town Hall and Mt. Hollis, downtown Holliston and Blair Square. The Stroll stops at Blair Square and the Historical Society, two of the same places that host the Halloween events. The difference is that the trolley connects them for you.
At Legacy Fine Homes & Estates, we pay attention to the calendars that local groups like these keep, because they show how a town really works week to week. If you're thinking about what Holliston's year looks like from your own front door, or you want to talk through a move within MetroWest, contact us and we'll share what we know.
