Milford Pumpkin Festival 2026 Lights Up the Fall Season

When the leaves start turning amber in Milford, the town’s downtown oval transforms into a bustling autumn playground. This year’s Pumpkin Festival, back for its 2026 edition, kicked off on Saturday morning with a crisp, cool breeze that smelled faintly of cinnamon and fresh‑baked pies.

First on the agenda was the much‑loved pumpkin weigh‑off. Locals hauled in everything from modest 30‑pound gourds to a behemoth that tipped the scales at over 400 pounds, prompting a collective gasp and a flurry of photo‑snaps. The winning pumpkin earned a hefty cash prize and, of course, bragging rights that will echo through the community for months to come.

Carving stations dotted the perimeter of the oval, where families huddled around tables, knives flashing as they transformed ordinary pumpkins into eerie lanterns and whimsical works of art. Kids giggled, parents offered tips, and the scent of fresh pumpkin flesh mingled with the distant aroma of roasted nuts from a nearby vendor.

As the sun dipped lower, the town hall’s iconic pumpkin was lit, its golden glow spilling over the crowd. That cue marked the start of the haunted trail – a winding path through decorated arches, fog machines, and costumed actors that sent shivers down even the bravest teenagers’s spines.

If you’d rather keep the scares at bay, there’s plenty else to explore. Artisans displayed hand‑crafted jewelry, knitted scarves, and autumn‑themed décor, while food trucks offered everything from hearty stew to caramel‑drizzled apple fritters. And when the music kicked in, local bands took the stage, filling the air with folk tunes and upbeat rock that kept feet tapping well into the evening.

The festival officially wrapped up at 9 p.m. on Saturday, but the energy lingered. Sunday’s schedule, running from 10 a.m. to 3 p.m., gave a more relaxed vibe – perfect for a leisurely stroll, a final bite of pumpkin‑spiced latte, or one last glance at the illuminated town hall pumpkin before the weekend fades.