Photo Gallery: Trunk or Treat 2026

Above: Trick or treating fun started early this year at the Town’s big Trunk or Treat. (photos by Beth Melo)

This weekend was the Town’s early Halloween celebration, Trunk or Treat. I’m sharing photo highlights from the day. (If you haven’t stocked up on candy for this Saturday’s door-to-door trick or treating yet, let this serve as your reminder!!)

Although most of the pics below are mine, some are contributed or from Town social media. (For photo credits, click on thumbnails.)

The gorgeous weather and bright foliage backdrop were treats of their own on Saturday. (Although, the sun may have made some of the tricked out attendees a bit warm in their costumes.)

As usual, the fun kicked off with the Southborough Fire Association’s party and costume contest at the Fire Station. I was too busy at the Friends of/Southborough Library’s table to pop in. But I can share pictures of two confirmed prize winners from their costume contest. This year’s Chief’s choice prize winner was Ava Ocnos. I also snapped a pic of the SFA’s winner for “cutest” costume:

This year's grand Chief's choice costume contest winner was Ava Ocnos (contributed photo) Ava Ocnos (contributed photo) (photo by Beth Melo)

At the event in Woodward’s parking lot, I’m sure many other great costumes were inspired by aspirations of winning prizes in SFA’s contest. Here are some of the trick or treaters’ costumes I enjoyed, including family themes:

 Attendees went all out on costumes for the SFA contest and enjoying trick or treating at trunks (photo by Beth Melo) Family theme costumes, like the Addams Family, are a hoot. (photo by Beth Melo) Fast food family fun (photo by Beth Melo) Marathon themed family (photo by Beth Melo) Willie Wonka inspired siblings picked out their own costume theme perfect for a day all about the candy! (photo by Beth Melo) Jurassic Park family themed costume (photo by Beth Melo) Even dogs got into the costume fun (photo by Beth Melo)

The “Trunk or Treat” event is named after the decorated trunks and vehicles that kids trick or treated at in Woodward parking lot. (Although, not every group used an actual vehicle.)

Participating “trunks”, tables, and exhibits were run by Town departments, local businesses, and volunteers from community groups.

Recreation went with a Sandlot theme (images cropped from Rec Facebook post)The event hosts, Southborough Rec, went with a “Sandlot” youth baseball theme this year:

Southborough Youth & Family Services can always be counted to go all in on their theme. This year, they embraced pirate fun — forcing kids to walk the planks (past shark fins) to get to the treats:

SYFS pirate crew (from SYFS Facebook post) Southborough Youth & Family Services embraced a Pirate theme with interactive fun this year. (photo by Beth Melo) Kids were excited to walk SYFS' planks, avoiding sharks in the water (photo by Beth Melo)

Skyrise Theater created another magical experience for kids. This year, the actors challenged trick or treaters to brave their way past dragons to trick or treat at their prop castle:

Skyrise Theater used their castle and dragon themed props and costumes (photo by Beth Melo) Skyrise asked kids to brave their way past dragons to trick or treat at the castle (photo by Beth Melo) Reaching the tower is no problem for a dragon! (photo from Skyrise Facebook post)

Southborough Youth Basketball Association is always inviting kids to shoot hoops at community events. But this is the only event that puts the hoops inside a trunk!:

SYBA played up on the hoops theme for their trunk (photo by Beth Melo) 

Ted’s of Fayville’s hauled in their extra long haunted flatbed truck again. In another business’ truck, the giant inflatable pumpkin skeleton also made a return (with a grim buddy).

Ted's Towing always makes the most of it's long truck (photo by Beth Melo) Looks like Ted's may need a couple of new hires for their crew! (photo by Beth Melo) large inflatables added to the Halloween decor (photo by Beth Melo)

Middlesex Savings Bank returned with their popular ATM (Automated Treat Machine)

Kids cashed in on Middlesex Savings Bank's popular ATM (Automated Treat Machine) (photo by Beth Melo)

Other highlights included the Police Dept handing out candy in front of a spooky crime lab and a Southborough Fire Department’s trunk trunk that was just “fire”. Other participants included St. Matthew’s Church, Friends of Southborough Recreation, Mathnesium, and Goldfish Swim School.

SPD went with a spooky Crime Lab theme (photo by Beth Melo) (photo by Beth Melo) St. Matthews went tropical with their theme (image cropped fro Southborough Rec post) The St. Matthew's crew chilled at their beach hangout (photo by Beth Melo) Friends of Southborough Rec Ice Cream themed Trunk (photo by Beth Melo) Mathnasium challenged kids with math problems (image cropped from Rec Facebook post) Goldfish Swim School used an ocean theme to engage potential swimmers (photo by Beth Melo)

Also supporting the event (but not pictured) were the DPW, Girl Scouts, and the Library’s table (where trick or treaters were encouraged to check out bookmarks to color with their candy).

(To view photos from past community events, click here.)

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