When South Boston’s inaugural StoopFest hits the streets, one of the driving forces behind the scenes will be local comedian and music enthusiast Jay Gillespie. Known for his sharp wit and generous spirit, Jay has stepped up in a big way to help South Boston NDC Event Planner Jenni McNeill bring this grassroots musical celebration to life — and he couldn’t be more excited.

A conceptual proposal initiated by South Boston NDC to transform the historic South Boston High School into affordable senior housing has won first place in the 25th Annual Affordable Housing Development Competition, hosted by the Federal Home Loan Bank of Boston (FHLBank Boston).

While the building is not currently available for redevelopment, the project — titled The Mosaic — was developed as a design and feasibility exercise in collaboration with graduate students from Harvard University, MIT, and Wentworth Institute of Technology. South Boston NDC served as the development sponsor, working alongside Davis Square Architects and finance mentor David Aiken.

South Boston NDC Executive Director Donna Brown testified about the importance of trees in the neighborhood during Boston City Councilor Ed Flynn’s public hearing last week to address the urgent need to expand the urban tree canopy in District 2. (And just days after the hearing, street trees were planted in front of Patriot Homes!)

CREW Boston recently honored Donna Brown, Executive Director of South Boston Neighborhood Development Corporation (South Boston NDC), with the 2025 Suzanne King Public Service Award, celebrating her decades of impact in the community development field and her unwavering commitment to affordable housing in South Boston.

When Brooke Patterson and Christina Valle of Wave Collective heard about South Boston StoopFest, they knew they had to help.

As South Boston NDC event planner Jenni McNeill was mentioning the new event during a South Boston Chamber of Commerce networking session, “I feel like Christina and I, our eyes lit up, and we were like, ‘Oh my gosh, so much fun. How can we help?’ We're all so passionate about Boston and local ties and really just wanting to grow anywhere that we can,” said Brooke.

The StoopFest logo isn’t just a design — it’s a symbol of South Boston’s character, history, and sense of community.

Created by local artist Maureen Garrity, the logo draws inspiration from the neighborhood’s iconic triple-deckers, capturing the welcoming spirit that defines Southie.