When autumn sweeps through New England, small towns don’t just celebrate—they glow. Pumpkins spill across town squares, barns, and church lawns, carved into grinning faces, flickering lanterns, and towering displays that turn quiet streets into glowing wonderlands. At night, the effect is nothing short of magical, as thousands of candles transform these historic towns into scenes that feel lifted from a storybook.
These 9 New England pumpkin festivals don’t just light up the night—they ignite a sense of community, wonder, and seasonal joy that lingers long after the candles burn out.
Keene Pumpkin Festival
Keene’s Pumpkin Festival is a dazzling spectacle of light and community spirit. Each year, volunteers and residents craft thousands of pumpkins, transforming the town into a radiant display. Carving creativity knows no bounds, from simple faces to elaborate scenes.
The festival features live music, food stalls, and family contests, drawing crowds from across the region. Keene’s civic pride shines as the event supports local causes. The glow of countless candles creates an unforgettable atmosphere, making this festival a staple of autumn traditions.
Jack-O-Lantern Spectacular (Roger Williams Park Zoo)
The Jack-O-Lantern Spectacular at Roger Williams Park Zoo elevates pumpkin artistry to a new level. Thousands of hand-carved pumpkins form a glowing narrative along an evening trail. Themed displays, larger-than-life sculptures, and intricate scenes captivate visitors.
With soundtracks and dynamic lighting, the experience transcends ordinary jack-o’-lanterns. Timed entries ensure a smooth visit, while vendors offer seasonal treats. The cinematic path combines atmosphere and creativity, attracting visitors from all over southern New England. It’s a communal celebration of fall artistry.
The Great Jack O’Lantern Journey (Southwick’s Zoo)
Southwick’s Zoo offers a magical experience with its Great Jack O’Lantern Journey. Thousands of pumpkins light the path, creating whimsical scenes and themed displays. Skilled carvers transform gourds into artistic interpretations of animals, storybook characters, and seasonal motifs.
The zoo’s atmosphere is enhanced by food vendors, music, and family-friendly programming. The event encourages repeat visits with its ever-changing designs. It’s an evening outing that blends craft, entertainment, and the cozy essence of fall, cherished by many families.
The Incredible Naumkeag Pumpkin Show
Naumkeag’s Incredible Pumpkin Show is a visual delight. The historic estate becomes a candlelit fantasy as thousands of pumpkins adorn its gardens. Curated scenes mix humor and seasonal motifs to contrast the Gilded Age elegance.
Volunteers and staff craft vignettes with careful lighting, highlighting the property’s architecture. Timed entries and shuttles manage the flow of visitors. The artistic juxtaposition against classic gardens is uniquely picturesque, drawing photographers and families alike. It’s an unexpectedly poetic celebration of pumpkin artistry.
Halloween on the Hill (Long Hill)
Halloween on the Hill at Long Hill is a charming after-dark stroll. The garden transforms with hundreds of glowing jack-o’-lanterns, seasonal displays, and themed vignettes. Visitors enjoy the intimate scale, with costumed volunteers, music, and artisan vendors enhancing the experience.
Carefully curated lighting maintains a cozy ambiance. The event feels like a neighborhood celebration, emphasizing small-town spirit and photography opportunities. It’s a gentle, family-friendly outing, allowing guests to enjoy the historic views amidst autumn’s beauty.
Damariscotta Pumpkinfest & Regatta
Damariscotta Pumpkinfest & Regatta is a unique coastal celebration. Oversized pumpkins, artist displays, and quirky pumpkinboat races define this event. Main Street fills with decorated gourds, carved jack-o’-lanterns, parades, and vendor booths.
While daylight races grab attention, evening displays illuminate the harbor, creating picture-perfect scenes. The festival blends agriculture, artistry, and community warmth, making it a beloved autumn gathering. Visitors from all over the region flock to participate, enjoying the creative spirit and hospitality.
Jack-O-Lantern Walk — Mystic Seaport Museum
Mystic Seaport Museum’s Jack-O-Lantern Walk is a maritime Halloween wonder. Shipyard lanes and historic buildings receive a candlelit transformation with hundreds of carved pumpkins. The coastal atmosphere is enhanced by campfires, live music, and family programs. Community involvement includes carving sessions and costume parades.
The combination of wooden vessels, salted air, and flickering gourds creates a distinct mood. It offers families a gentler Halloween experience, tied to New England’s seafaring heritage. It’s a favorite for those seeking intimate, atmospheric outings.
Camp Sunshine Pumpkin Festival
Camp Sunshine’s Pumpkin Festival in Freeport offers a heartwarming spectacle. Thousands of jack-o’-lanterns light up the night, supporting a nonprofit for children with life-threatening illnesses. The family-friendly event includes live music, food vendors, crafts, and a ceremonial lighting.
Volunteers carve and arrange pumpkins, adding emotional depth. The festival radiates warmth, blending community and charity. Visitors enjoy an autumn night out while contributing to an important cause. It’s a return-worthy event for its communal spirit and joyous atmosphere.
Winooski Festival of Pumpkins
Winooski’s Festival of Pumpkins lights up the city with creativity. Rows of jack-o’-lanterns line downtown streets, reflecting the community’s character. Residents, students, and businesses contribute to the glow. Nighttime events include live music, family activities, and food trucks.
The festival fosters a sense of belonging, with friendly contests and storytelling. Visitors appreciate Winooski’s small-city charm and grassroots spirit. It’s a festive start to Halloween, offering photo-worthy moments and neighborly warmth. The event captures the essence of community celebration.