WHITMAN - Whitman’s cherished civic ritual, the annual WinterFest, which spanned two decades, began as a simple idea on a miserable day and evolved into one of the town’s most successful volunteer-led celebrations before concluding due to volunteer fatigue in 2015. The event, which transitioned from a traditional holiday festival to the innovative “First Night” cookie drop, left a lasting physical and cultural legacy on the South Shore town.
The Cold Origin of a Warm Tradition
The impulse for WinterFest, which ran from approximately 1994 through 2013, emerged from the mind of local resident and committee chairman, Richard Rosen. In the early 90s, Rosen was driving through Whitman Center on a cold, blustery day and decided the town needed brightening up. Inspired by childhood memories of the downtown merchants association decorating the streets, Rosen sought to raise funds for eight strands of lights to hang over the town center.
His vision was to create a non-political, non-religious event focused entirely on community fun, free of cost to families. Early fundraising surpassed expectations, securing enough money not for eight, but for 24 strands of decorative lights.
Organizers, Community Muscle, and the Sweet Pivot
The success of the Whitman WinterFest rested on the shoulders of its dedicated organizers and a unique, privately funded model. The driving force was Richard Rosen, who served as the chairman of the Winterfest Committee for all twenty years, utilizing a hands-on “civic entrepreneurship” approach. He was joined by a core cadre of devoted volunteers, notably David Menard, a local jeweler whose creative contributions proved vital. This private committee organized and funded the entire event, which meant it was entirely shielded from municipal budget constraints.
The traditional WinterFest, typically held on a Sunday in early December, offered free events open to the public. For 15 years, it also featured a lively summer carnival at Memorial Field or Town Park. While the committee maintained financial independence, the logistical success relied heavily on cooperation from town departments, including the Whitman Police Department, the Whitman Fire Department, and the Department of Public Works, whose help Rosen continually acknowledged in interviews.
The Classic Era: Horsepower, Hot Dogs, and Holiday Spirit
For nearly two decades, the annual WinterFest, typically held on a Sunday in early December, served as the town’s primary holiday opener, building momentum through classic, family-friendly attractions.
By the 16th annual celebration on Sunday, December 6, 2009, the event had evolved significantly while retaining its core traditions. Attendees could enjoy free activities that included horse-drawn hayrides, trolley rides, and pony rides. Entertainment spanned the traditional and the competitive, offering rock climbing, face painting, and a popular opportunity for children to take pictures with Santa Claus at Mutual Bank. Musical performances often highlighted local talent, featuring the Whitman-Hanson chorus and band.
In addition to staple attractions like the children’s pie-eating contest, the 2009 event marked the debut of the first annual adult hot dog eating contest, which was limited to ten contestants over the age of 18. Although the Town Hall was unavailable that year due to a Special Election, the event moved forward successfully. Visitors could purchase commemorative Winterfest buttons at most stores located in Whitman Center. The success of these events relied on coordination with the Whitman Police Department, the Fire Department, and the Department of Public Works, operating entirely on private funding.
The 125th Anniversary: A Year of Grand Celebration (2000)
The core organizers of WinterFest often assumed the role of managing other large town celebrations, most notably leading the entire year-long observance of Whitman’s 125th anniversary (quasquicentennial) in 2000.
The WinterFest Committee chairman, Richard Rosen, also chaired the 125th Anniversary Committee, which planned 10 separate events during the year. This ambitious campaign started with a formal dinner dance held at Ritter Country Club on Saturday, April 1st, which swiftly sold out. Other events included a road race and a chicken bake.
The festivities culminated on June 11th with a spectacular parade that retrospectives described as the largest Whitman had ever seen. The committee took initial funding, initially deemed politically sensitive, providing seed money for printing tickets and reserving halls, but eventually managed to give most of the appropriated funds back to the town. As a lasting physical marker of the celebration, the committee oversaw the burial of a time capsule on the Town Hall lawn, sealed with instructions for its opening in the year 2075.
Not to be outdone, much of the WinterFest committee reunited in 2025 to oversee the 150th anniversary. It managed to pull together a bigger parade and a time capsule on the other side of Town Hall, among other events throughout 2025.
The Final Bow: The Revolutionary First Night (2013-2015)
In its concluding years, the committee executed a strategic pivot from the traditional daytime holiday celebration to an innovative “First Night” New Year’s Eve format, held on December 31st. This move coincided with the 75th anniversary of the creation of the Toll House cookie, invented in Whitman.
The inaugural First Night Whitman on December 31, 2013, launched the event’s defining icon: the Midnight Cookie Drop. A massive, lighted replica of a Toll House cookie, measuring six feet in diameter (or 75 inches) and fabricated by students at South Shore Vocational Technical High School, was hoisted by a crane 75 feet above Duval’s Pharmacy in the town center. The spectacle culminated with the cookie dropping at the stroke of midnight, followed by a professional pyrotechnic show launched from the pharmacy’s roof. In honor of the vocational students’ contribution, the Board of Selectmen declared the day “South Shore Vocational Technical Day”.
The evening included professional entertainment, notably three hired bands who performed on a stage constructed from ramp trucks located at the corner of Temple Street and Washington Street, entertaining the crowds from 9:00 p.m. until roughly 12:30 a.m.. For instance, the band 6 Foot Sunday concluded their final set just 12 seconds before the midnight countdown. The committee distributed complimentary items, including 2,014 homemade Toll House cookies, loud horns, and Whitman First Night lip balms. The entire event was free of charge, made possible by securing funding from Nestle. Proceeds generated from the sales of commemorative First Night buttons went directly to benefit the Whitman Food Pantry.
The End of an Era
The traditional WinterFest celebration officially concluded after its 20th anniversary year in 2013. In September 2014, Chairman Richard Rosen informed the Board of Selectmen that the WinterFest Committee had voted unanimously to cease doing the annual event.
Rosen cited the cumulative reasons for the dissolution, explaining that the high-intensity organization required an “extravagant amount of work” and noting that the dedicated core volunteers were facing burnout and had aged over the two decades of service. Despite numerous attempts over the years to recruit new members, the committee found that few people stepped up to commit to the ongoing work.
Upon the announcement, town officials expressed surprise and regret, with Selectman Brian Bezanson stating he was “bummed out,” as he had hoped the festival would expand. The committee did receive approval to host at least one more First Night celebration, as it was less logistically demanding than the full WinterFest calendar.
A Legacy of Lasting Impact
The legacy of the WinterFest Committee extends beyond the temporary joy of its celebrations, leaving behind permanent contributions to Whitman’s civic landscape.
The most tangible achievement is the Whitman Town Park Playground. The committee spearheaded a successful effort to raise $125,000 for its construction, creating a lasting asset for the town’s children. Additionally, Nestle’s partnership for the initial First Night celebration included a $50,000 donation specifically toward the playground effort.
The committee also established a unique cultural identity for the town with the highly popular First Night Cookie Drop, cementing Whitman’s status as the birthplace of the Toll House cookie. The proceeds from the commemorative First Night buttons sold for these New Year’s Eve events were designated to benefit the Whitman Food Pantry, supporting the town’s social safety net.
Ultimately, the Whitman WinterFest demonstrated a distinctive model of sustained, self-funded community engagement that fostered local pride and unity for two decades. The tradition reinforced the belief that community involvement can fundamentally improve a town’s quality of life.
