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| Photos with Santa and Mrs. Claus are one of the many highly-anticipated events that happen at the annual Windham-Raymond Athletic Boosters Holiday Fair which occured on Nov. 15 and 16 at WHS. COURTESY PHOTO |
The Windham-Raymond Athletic Boosters celebrated another successful year as their 33rd Annual Holiday Fair filled Windham High School on Nov. 15 and 16 with festive energy, strong community spirit, and record participation. Hundreds of visitors from across Southern Maine and beyond crowded into the high school gymnasium and hallways over the two-day event, browsing the work of more than 140 crafters, local makers, and student-run groups.
This year’s event featured over ten student clubs and athletic teams, including the Classes of 2026, 2027, 2028, and 2029, the National Honor Society, Student Council, the Alpine Ski Team, and the Track Team. While final tallies are still being collected, each group took advantage of the weekend’s steady crowds to raise funds through a variety of handmade goods, treats, and creative items.
Santa and Mrs. Claus made their annual appearance at 10 a.m. both Saturday and Sunday, drawing steady lines of excited children. Approximately 90 photos with Santa were taken this year, and families can find the images posted on sgirardphotography.com.
Inside the gym, aisles were shoulder-to-shoulder for much of Saturday, especially between the peak hours of 10:30 a.m. and 2:30 p.m. Vendors reported strong sales throughout the weekend, while Sunday brought its typical slightly slower but still steady midday rush.
Concessions Alley once again lived up to its reputation as one of the fair’s most popular stops. Families of student athletes donated homemade crockpot meals, desserts, and snacks, nearly all of which sold out before 1 p.m. both days. The fair also featured a vendor raffle with 64 donated items and a busy 50/50 table.
Altogether, the Holiday Fair generates nearly $25,000 annually for the Boosters, making it the organization’s largest fundraiser. Proceeds come from space rentals, raffle ticket sales, concessions, and vendor contributions. The Windham Raymond Athletic Boosters is a nonprofit organization that is independent from the RSU 14 Athletic Department. The proceeds help support the athletic programs helping to cover things like team equipment bags, warm-ups, equipment like nets, goals, mats and more.
The event relies heavily on volunteer support. The Boosters Board, which includes 12 members and two craft fair co-chairs, is involved in year-round planning, but as many as 20 additional volunteers assist on both Saturday and Sunday of the fair. “As early as 2 p.m. Friday, we have people mapping the gym floor while others unload tables and chairs from the delivery truck,” said co-chair Ernesta Kennedy. Volunteers help crafters unload, serve as “table watchers” so vendors can take short breaks, staff concessions, sell 50/50 tickets, and oversee the raffle area. This year’s setup and cleanup numbers were the strongest ever, thanks especially to student participation.
Interest from crafters remains incredibly high. The fair fills quickly every year and maintains a waitlist of nearly 50 vendors. Once a crafter secures a booth, they seldom give it up, making the rotation limited. Kennedy noted that the team is exploring options for expanding in future years to accommodate the growing demand.
Planning for next year begins almost immediately. For those hoping to get involved next year, whether as a volunteer, planner, or vendor, the Boosters encourage reaching out. The best point of contact for the holiday fair is windhamboosters@yahoo.com. For other Booster related inquiries please email athleticboosters@rsu14.org
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