Friday, October 9, 2026

Windham Trunk or Treat brings families together for a night of Halloween fun

By Masha Yurkevich

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.

Windham Parks and Recreation's popular annual Trunk or 
Treat event for children returns from 5:30 to 7:30 on
Saturday, Oct. 24 in the parking lot behind the Windham
Mall. Trunk hosts can register through Oct. 19 while
families can register through Wednesday, Oct. 21. 
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The event will take place from 5:30 to 7:30 p.m. in the parking lot directly behind the Windham Mall near Hannaford and Renys. Local families can expect an evening filled with decorated vehicles, candy, music, dancing, snacks and Halloween costumes.

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. <

Friday, October 2, 2026

Time remains to attend 154th Cumberland County Fair

By Ed Pierce

If you may have missed a chance to attend the 154th Cumberland County Fair because of last weekend’s nor’easter, there’s still time to experience all the fair has to offer by the time the annual event wraps up Saturday evening at the fairgrounds in Cumberland.

Despite the rain last weekend, the 154th Cumberland County 
Fair continues from 8 a.m. to 8 p.m. through Saturday,
Oct. 3 and offers plenty of live entertainment, livestock
exhibits, food, rides, fireworks and fun for families at the
fairgrounds, 196 Blanchard Road in Cumberland.
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The schedule of events for both Friday and Saturday are filled with events sure to please just about everyone. There will be plenty to see and do including live music and entertainment, an array of livestock, food, and flower exhibits, carnival rides, a draft horse and pony show, candy making demonstrations, pig races, a truck pull, harness racing and fireworks to close out the fair on Saturday night.

Attending the Cumberland County Fair is a tradition that stretches all the way back to Oct. 7, 1869, when a two-day event was held on the grounds of what is now Greely High School. In 1874, the Cumberland Farmer’s Club moved the fair to newly purchased grounds in West Cumberland that included a fenced-in trotting park. By 1952, the fair was officially renamed the “Cumberland County Fair” and became a popular annual event attended by thousands of Cumberland County residents each fall.

During the final two days of this year’s fair on Friday, Oct. 2 and Saturday, Oct. 3, the fair will be open from 8 a.m. to 9 p.m.

Scheduled events for Friday include the MSTTP Tractor Pull featuring Modified Big Rigs and Semi pulls; musical performances by singer-songwriters Ryan Halliburton and Henry Lowery, The World Famous Grassholes, and The Jack Fossett Band; magic and comedy from Joe Howard; the Nettie Loops Hula Hoop Experience; Sweepstakes Horse Memorial Pulls; and a Draft Horse and Pony Show.

Also on Friday, the fair’s Gillette Midway will be open for carnival rides weather permitting. There will be antique sawmill demonstrations, Maine maple sugar and syrup tasting, harness racing, antique hay press demonstrations, 4-H working steers, a 4-H dairy clipping contest, pig racing, cooking and crafting demonstrations, booths, vendors, and three-horse hitch distance pulls.

Saturday’s scheduled events include a pig scramble; farmer’s horse and ox pulls; MSTTP Truck Pulls; magic from Wes Wonder; a Kids Ox Pull; musical performances by 43 Degrees North, Dark Horse, Chase Jobe, Timothy James & Band, and Julia Gagnon & Friends; comedy juggling and dangerous stunts by Showtime Steve; and the fair concludes with a spectacular fireworks show around 8:30 p.m. by Central Maine Pyrotechnics.

Also on Saturday, fair visitors can watch a Rabbit show, view cooking and crafts demonstrations; farmer’s draft horse, mule and pony events, draft horse log twitches, a calf scramble, 4-H dairy and working steer shows, a youth poultry show, Quilts of Valor presentations, Sheep, Dairy, Swine, Goat and Beef livestock showings, antique sawmill demonstrations, midway carnival rides, booths, vendors, tours of the maple sugar house, and lots of tasty food to experience.

Visitors can stroll through exhibition barns filled with blue-ribbon vegetables, flowers, crafts and pies, cakes and other baked goods, and award-winning locally grown huge pumpkins. Or they can see up close the John Deere display of the latest models of tractors. 

Theodore Googins of Gray is this year’s fair president with Lincoln Merrill of North Yarmouth as vice president and Jeff Steinman of Cumberland serving as vice president and treasurer. Elizabeth Tarantino of Cumberland is fair secretary, Mark Cooper, Sonja Nielsen and Richard Morrill, all of Windham, are serving on the fair’s Board of Directors with Cooper also overseeing the fair’s livestock area.

Admission to the 154th Cumberland County Fair is $15 cash for adults with kids ages 12 and under admitted for free.

The fairgrounds are located at 196 Blanchard Road in Cumberland. Plenty of convenient free parking is available.

To learn more about the 154th Cumberland County Fair and view a complete schedule of events visit https://cumberlandfair.com/ or find them on Facebook under Cumberland Fair. <