How Trick-or-Treating Has Evolved in the Monadnock Region

As Halloween approaches, neighborhoods throughout the Monadnock Region are preparing for a familiar sight: children dressed as witches, superheroes, ghosts and other characters making their way from house to house in search of candy. But alongside traditional porch lights and doorbells, another Halloween custom has become increasingly visible. Decorated car trunks, community gathering spaces and downtown businesses are offering families new ways to celebrate, expanding a tradition that has evolved considerably over centuries. Known as "trunk-or-treating," the practice brings families together in parking lots or designated areas, where volunteers decorate their vehicles and distribute candy to children. Rather than traveling from doorstep to doorstep, participants move between cars, often enjoying costume contests, games and other activities along the way. Across southwestern New Hampshire, these organized gatherings have become part of a broader Halloween calendar, complementing traditional neighborhood trick-or-treating while providing additional opportunities for community involvement. From Keene's pumpkin-filled downtown to smaller celebrations in Swanzey, Winchester and surrounding communities, Halloween in the Monadnock Region reflects both the enduring appeal of old traditions and the growing variety of ways families can participate. A tradition centuries in the making Although trick-or-treating has become synonymous with American Halloween celebrations, its origins extend far beyond the familiar practice of handing out candy. Historians trace some of Halloween's earliest influences to Samhain, an ancient Celtic festival marking the end of the harvest season and the beginning of winter. Celebrated around the start of November, Samhain is associated with beliefs about the boundary between the living and the dead becoming less distinct. Over time, these customs blended with Christian observances, including All Saints' Day and All Souls' Day. During the Middle Ages, a practice known as "souling" involved people traveling from home to home asking for food, particularly small pastries called soul cakes, in exchange for prayers in honor of deceased family members. In Ireland and Scotland, a related tradition called "guising" saw children dress in costumes and visit neighboring households — sometimes performing songs, jokes or poems in exchange for food or small gifts. Irish and Scottish immigrants helped bring Halloween customs to the United States during the 19th century, but the modern American version of trick-or-treating did not become widespread until the 20th century. By the 1920s and 1930s, Halloween pranks and mischief had become common in some communities, prompting efforts to promote organized, family-friendly celebrations. Following World War II, trick-or-treating gained popularity as suburban neighborhoods expanded, sugar rationing ended and candy manufacturers began marketing products specifically for Halloween. By the 1950s, children going door to door in costume became a recognizable part of American life. From neighborhood streets to decorated trunks While traditional trick-or-treating remains a familiar Halloween activity, trunk-or-treat events have introduced another way for communities to participate. At these gatherings, organizers designate a parking lot or similar space where participants decorate their vehicles with Halloween displays. Children then walk between the vehicles to collect candy, often accompanied by family members. For families living in rural communities, where homes may be separated by longer driveways, dark roads or considerable distances, concentrated trick-or-treating events can offer a convenient alternative. They can also provide a manageable setting for parents with younger children or families who prefer organized activities. The Monadnock Region's 2026 Halloween calendar provides several examples of this approach. In North Swanzey, Da Brothers Contractors hosted a free trunk-or-treat event on Oct. 17, inviting families to collect candy from decorated vehicles while encouraging participants to decorate their own trunks and distribute treats. A week later, Swanzey's eighth annual Halloween Block Party at Brown Memorial Field, held Oct. 24, combined trunk-or-treating with a costume contest, haunted trail and other family activities. Meanwhile, the ELMM Community Center in Winchester has scheduled its annual trunk-or-treat and Kiwanis Costume Contest for Saturday, Oct. 31, during the town's designated trick-or-treating hours. The event includes prizes for decorated vehicles, with categories recognizing creativity, humor and scariness. A Halloween identity shaped by pumpkins and community Few places in New England have established a Halloween identity quite like Keene, where the annual Pumpkin Festival has become one of the region's most recognizable autumn traditions. The festival began in 1991 as a downtown harvest celebration organized by local merchants hoping to attract visitors and bring renewed activity to the city's commercial center. Over the following decades, the gathering grew into an event known nationally for its elaborate displays of carved pumpkins. In 2013, Keene set a Guinness World Record with 30,581 illuminated jack-o'-lanterns displayed in one location, cementing its reputation as a destination for Halloween enthusiasts. This year's Pumpkin Festival, held Oct. 17, featured carved pumpkin displays, live entertainment, children's activities and a costume parade. Participating downtown businesses also welcomed costumed children for trick-or-treating between 3 and 5 p.m. Beyond Keene, smaller towns throughout the Monadnock Region have developed their own approaches to the holiday. In Sullivan, a Halloween in the Park celebration scheduled for Friday, Oct. 30, at Jewett Park will feature illuminated pathways, treat stations, games, prizes and a costume parade. Organizers are also planning to serve hot cocoa and apple cider, incorporating familiar autumn traditions into the festivities. Meanwhile, Keene's Family Resource Center at HCS has scheduled a Candy Crawl for Thursday, Oct. 29, allowing children to collect treats from community partners and employees. The event also includes crafts and a sensory-friendly room, providing an option for families seeking a quieter Halloween experience. These celebrations highlight how Halloween extends beyond collecting candy, incorporating opportunities for creativity, social interaction and community participation. Keeping old traditions alive Despite the emergence of new celebrations, traditional door-to-door trick-or-treating remains an important part of Halloween in the Monadnock Region. In Keene, city officials have designated Saturday, Oct. 31, from 5:30 to 7:30 p.m. as this year's official trick-or-treating hours. The city encourages adults to accompany children, use flashlights and reflective clothing, and remain attentive to traffic. Residents who wish to welcome trick-or-treaters are encouraged to leave their exterior lights on. For many families, traditional trick-or-treating offers children an opportunity to explore their neighborhoods, interact with neighbors and participate in a shared experience that often becomes a lasting childhood memory. Trunk-or-treat events provide a different experience, concentrating activities within designated spaces and often involving organizations and volunteers who might not otherwise participate in residential trick-or-treating. Each format has its advantages, and the two traditions can coexist, allowing families to attend community events throughout October before heading into their neighborhoods on Halloween night. The continued evolution of Halloween reflects the holiday's adaptability, particularly in a region characterized by small towns, rural landscapes and longstanding autumn traditions. Whether children are climbing a neighbor's front steps, visiting a downtown business or stopping at a decorated tailgate, the tradition continues to serve much the same purpose it has for generations. Halloween may look different from one community to another, but in the Monadnock Region, its enduring appeal lies in the opportunity to celebrate together.