Holy Cross Wine & Cheese Festival

About the Event

The Holy Cross Wine & Cheese Festival is a lively summer street festival in Indianapolis that brings together neighbors, food lovers, wine fans, and families for an evening built around flavor and community. Held on the Sturm Avenue Esplanade in the historic Holy Cross neighborhood, it has the feel of a neighborhood block party with a polished culinary twist—part tasting event, part fundraiser, and part celebration of the near-eastside’s creative spirit.

What makes it special is the combination of approachable fun and curated experiences. Guests can sample wine and cheese, browse local vendor booths, enjoy live music, and take part in interactive food-focused activities. The atmosphere is welcoming and social, with plenty of reasons to linger, talk with neighbors, and discover new local favorites.

The Surrounding Area

Holy Cross sits on Indianapolis’s near-east side, in one of the city’s most historic residential neighborhoods. The festival takes place along the Sturm Avenue Esplanade, a distinctive street setting near the Arsenal Tech area and not far from downtown, which gives visitors an easy way to pair the event with other Indianapolis outings.

The surrounding area reflects the character of older Indianapolis neighborhoods: walkable streets, historic homes, and a strong sense of local identity. Visitors will also find themselves close to downtown dining, cultural attractions, and neighborhood businesses that make the east side feel connected to the city’s larger food and arts scene. It is an especially appealing part of Indianapolis for travelers who enjoy events with a true community feel rather than a large fairground setting.

Activities & Attractions

The festival is built around tasting and discovery. Core attractions include wine samples, cheese offerings, local vendors, and food-focused experiences. In past and current festival descriptions, guests have also been able to enjoy:

• Live music
• Cheese Wars / grilled cheese competitions
• A Somm Experience led by a sommelier
• A Kid’s Zone
• Beer garden offerings
• Local artisan and food vendors
• Silent auction items and special event extras

One of the most talked-about features is the culinary competition element, where local chefs prepare creative cheesy dishes for attendees to sample and vote on. The event also includes family-friendly activities, which makes it broad enough to appeal to adults looking for a tasting event and families wanting an evening out together. The mix of beverage tasting, entertainment, shopping, and interactive programming gives the festival a strong “something for everyone” feel.

Schedule & Logistics

For 2026, the Holy Cross Wine & Cheese Festival is scheduled for Saturday, July 25, 2026, from 4:00 PM to 9:00 PM. The event is hosted at 435 Sturm Ave, on the Sturm Avenue Esplanade between N Arsenal Ave and N State Ave in Indianapolis.

The festival is ticketed, with tickets sold through OnTap. Based on previous festival formats, tickets may be used for items such as wine samples, drinks, cheese trays, and other special tasting experiences. Some premium experiences, including guided tasting sessions, may require separate pre-purchased passes.

The event is designed to be family friendly and has previously been described as a rain or shine gathering. Parking is typically handled through nearby street and neighborhood options, so visitors should plan to arrive early and allow time to walk from surrounding blocks. Because the festival runs in the evening, it works well as both a dinner-adjacent outing and a longer social event.

History & Heritage

The Holy Cross Wine & Cheese Festival is a relatively new but fast-growing neighborhood tradition. It was created as an outgrowth of the Holy Cross community’s desire to strengthen quality of life, accessibility, and neighborhood connection on Indianapolis’s near east side. Organizers have described it as a major annual fundraiser for the Holy Cross Neighborhood Association and a signature event that supports safety, accessibility, and community pride.

The festival also carries a meaningful personal origin story. It was inspired in memory of Kelly Wensing, a community supporter and wine-and-cheese enthusiast whose love of local food and neighborhood life helped shape the event’s spirit. Over time, the festival has expanded from a small neighborhood gathering into a larger celebration that draws around 1,500 people, featuring dozens of vendors, multiple musical acts, and special tasting experiences.

Today, it stands as both a fundraiser and a celebration of Holy Cross identity: a way to honor the neighborhood’s history while creating a lively, welcoming event that brings residents and visitors together.