Sponsorship Opportunities

Why This Event Matters

The Holy Cross Wine & Cheese Festival is the neighborhood’s signature annual fundraiser, bringing about 1,500 people to the near eastside each summer. It’s a lively evening with food trucks, chefs, beverage partners, live music, and special experiences that keep people engaged and exploring the neighborhood.

Sponsorship dollars directly fund projects that make our neighborhood safer, more welcoming, and more beautiful for everyone. In the past, funds have gone toward significant projects like the Highland Park Memorial Sculpture, a testament to the power of community support. This year, we are focusing on various initiatives aimed at enhancing safety, accessibility, and community pride. Your sponsorship will support:

• Community Powered Infrastructure Projects: These projects focus on safety improvements, such as installing bike racks, painting curbs, creating bump outs, and improving paths to ensure our neighborhood is safe and accessible for everyone.

• Neighborhood Beautification and Community Building

  • Replacement of Holy Cross welcome signs and damaged utility-pole signage to create a cohesive, inviting neighborhood identity 

  • Restoration of traffic signal boxes along New York and Michigan Streets, where public art was removed during the 2-way conversion, helping deter graffiti and maintain visual appeal

  • Funding supplies for the Holy Cross Clean Team volunteers to keep Holy Cross Neighborhood clean and inviting year-round

By sponsoring the Holy Cross Wine & Cheese Festival, businesses invest in people, place, and pride - and become visible partners in a community that shows up and supports those who support it.

From a sponsor perspective, the festival has grown steadily each year.  Now featuring 35 vendors, multiple musical acts, beverage partners, and ticketed experiences, which means attendees stay, explore, and notice the businesses that make the event possible.

So this is really about both impact and exposure: your sponsorship helps build a stronger Holy Cross Neighborhood while putting your brand in front of a large, engaged local audience in a positive, memorable setting.