Connersville’s Winterfest Returns December 5–6 for Two Days of Holiday Cheer

Connersville’s 2025 Winterfest: A Downtown Holiday Celebration on December 5–6 Connersville, IN — Historic Downtown Connersville will once again transform into a festive holiday destination as the community gathers for Winterfest 2025, taking place Friday, December 5 from 3:30–8:30 PM and Saturday, December 6 from 12:30–8:30 PM.

Winterfest is an annual Connersville tradition that has been a cherished part of the community for decades. In recent years, organizers began reimagining the event to expand activities, enhance visitor experiences, and increase local participation. Now in its revitalized form, Winterfest continues to grow each season—bringing families, neighbors, and small businesses together to celebrate the spirit of the holidays. A Weekend Full of Holiday Activities Winterfest offers two days of festive programming for all ages, including live entertainment, family-friendly attractions, local shopping, and seasonal food offerings.

Guests can expect: Live music and performances at Market Street Plaza, The Oasis, and throughout downtown The Winter Sky Art Installation in the Court Street Alleyway Reindeer Games children’s activities on the Courthouse Lawn Visits with Santa and Mrs. Claus at Connersville’s Santa House A Craft & Farmers’ Market featuring local artisans along Central Avenue Winter Window Displays created by downtown businesses Carriage rides, holiday open houses, and special programming through partner locations Evening attractions including the Celebration of Lights and a Luminary Display on Central Avenue.

This year also introduces a new highlight: pony rides on Friday, adding another family-friendly attraction to the weekend lineup. Downtown Connersville: The Heart of Winterfest Most activities will take place in historic downtown Connersville, with the primary hub at Market Street Plaza. Additional programming will extend along the Central Avenue corridor, at local churches, the museum and Canal House, shops, and other partner venues—encouraging visitors to explore the entire downtown district. Local Vendors, Food Trucks & Holiday Shopping Winterfest proudly showcases Connersville’s small business community.

More than 25 local craft vendors will be on site, including Tomasino’s Bakery, Wildflowers & Whiskey, Chuck’s Woodshop, and others. Downtown stores will also be open with special holiday hours and offerings. Food options will be plentiful, with five food trucks and additional pop-ups serving seasonal favorites. This year’s lineup features: Pitmasters Privilege BBQ, Outlaw’s Deep Fried Chicken, Ginger Gringo, Sweet Dreams Homestead, Tomasino’s Bakery, Beach Blends, The Lemon Shack, and more. Strengthening Community & Supporting Local Revitalization Winterfest plays an important role in supporting Connersville’s downtown revitalization.

By bringing residents and visitors into the heart of the city, the event boosts local shopping, highlights small businesses, and fosters a sense of shared community pride. “Winterfest represents the best of Connersville—neighbors coming together, supporting local entrepreneurs, and creating memories that warm even the coldest months,” said organizer Brayton Johns. “There’s no time like Christmas in Connersville. Downtown is on the comeback, and events like this help spark that momentum.”

Parking & Visitor Information: Guests can find parking in designated downtown lots and along open side-street areas surrounding Central Avenue. Visitors are encouraged to arrive early for the best spots. Volunteers and signage will be available throughout the event to help guide attendees. Most Winterfest activities involve walking, so guests should dress for the weather and prepare to explore the downtown district.

Community-Powered & Volunteer-Driven Winterfest is made possible thanks to the collaboration of local organizations, downtown businesses, and a dedicated team of approximately 15 volunteers who donate their time and resources.

Donor highlights and sponsor recognition will be featured leading up to the event and onsite. For updates, vendor spotlights, and a full schedule, follow the official Historic Downtown Connersville Winterfest Facebook page and stay tuned for more announcements.