Families looking for a fun and family-friendly way to celebrate Halloween will have the chance to gather for Windham Parks and Recreation’s annual Trunk or Treat on Saturday, Oct. 24.
Kelsey Crowe, the deputy director for Windham Parks and Recreation, helps to lead the larger community events of the department, including the annual Trunk or Treat. Her responsibilities include coordinating volunteers, managing registration, promoting the event, and making sure the department has enough candy and supplies for the evening.
“It is a big community effort,” Crowe said.
Volunteer organizations, families and local businesses participate by decorating and hosting their own trunks. The Windham Mall provides a parking area, while Windham Fire Rescue and Windham Police help with the event by assisting with the area and keeping things organized. This year, Windham Parks and Recreation hopes to have more than 20 different trunks for children to visit. Each trunk will have its own decorations, and some will offer allergy-friendly treats, toys or other items.
In addition to trick-or-treating, a DJ will provide music throughout the evening, and families can visit the event trailer for snacks, hot chocolate and cider. There will be space for children and families who want to dance and enjoy the music together. For Crowe, one of the best parts of the event is seeing families enjoy the evening together.
“I always like to walk around these events and see families having fun and smiling and kids laughing,” Crowe said.
The event also offers an alternative to traditional trick-or-treating. Rather than traveling from house to house, families can stay in one central location, making it easier for parents and caregivers to keep track of children. Crowe said the setting also gives families a chance to enjoy Halloween without having to visit unfamiliar homes or neighborhoods.
The event has grown considerably since it began. In its earlier years, Trunk or Treat was held in the back parking lot at Windham Middle School. The event was later moved to its current location. During the COVID-19 pandemic, Parks and Recreation adapted the celebration into a drive-through Trunk or Treat, allowing hundreds of families to participate while remaining in their vehicles. Since then, the event has returned to a walking format.
Pre-registration and time slots have remained part of the process, helping organizers estimate attendance and ensure that trunk hosts have enough candy for participants and this year, Parks and Recreation expects about 400 to 500 children and families to participate.
One new addition this year is a sensory friendly time slot. Crowe said the regular event can sometimes become overwhelming for children who are sensitive to darkness, loud music or flashing lights. The new time slot will take place earlier, while it is still light outside, and will provide a quieter opportunity for children to participate.
The sensory friendly time slot has limited availability and is not listed on the website. Families interested in participating can call Windham Parks and Recreation to ask about the option.
Families are encouraged to wear costumes, and the department will also host a costume contest following the event. Goodie bags will include information about how families can submit photographs of their costumes for a chance to win prizes. Registration is required ahead of time so Parks and Recreation can plan for the expected number of participants.
Trunk hosts can register through Oct. 19, while families can register through Wednesday, Oct. 21.
For Crowe, the goal of the evening is simple: to give families a chance to have fun together and create positive Halloween memories.
“I just want families to have a fun night and get some free stuff and be excited for the following year and come back,” she said.
With decorated trunks, music, treats, activities and a growing community turnout, Windham Trunk or Treat is once again preparing to bring families together for an evening of Halloween fun. <

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