Transformational Thursdays

2023 Community Engagement Plan - DRI Projects - Webinar series

The Village of Ossining proudly presented a new webinar series: Transformational Thursdays. This series is an opportunity for those that live, work, and play here to participate in community engagement surrounding projects funded under the 2021 New York State Revitalization Initiative (DRI) award of $10 Million (Click here for the Press Release: Ossining Mid-Hudson Winner of 5th-Round DRI).

The series was designed for the community to learn about what is ahead for the Village, separated into subjects that build upon each other. There are eight topics of discussion that will include specific information regarding the innovative plans for the community’s future, with opportunities for the public to share their thoughts as a way to add dimension to the project concepts. The Village Board of Trustees and Village staff will lead these discussions.

We look forward to the community using these as a resource and guide to what residents and visitors can expect as these projects take shape. Recordings are available on the Village’s YouTube channel for those unable to attend these virtual sessions in real time. The Village is developing a “Frequently Asked Questions” page that can be translated into 100+ languages on our website.

It is important to the Village Board of Trustees to maintain and evolve its relationship with the Ossining community. While presenting our webinar series, we can connect the dots between our volunteers, staff, non-profit organizations, local businesses, and those that live here while ensuring that folks can ask questions and get answers.

Transformational Thursdays Q&A

Feel free to submit questions in advance to

Transformational Thursdays-What’s Happening Downtown?

What’s Happening Downtown?
May 4, 2023 @ 6:00 PM

Learn how the Downtown Revitalization Initiative (DRI) projects, along with the NYS Route 9 Road Diet, the redevelopment of Main and Spring Street lots, and the 5 Corners Intersection project work collectively to enhance Ossining’s vibrant and sustainable future. The Village will also be debuting our new interactive story map, which will allow residents and visitors to virtually learn more about ongoing projects Village-wide.

Filename Community Center(ed)

Community Center(ed)
May 11, 2023 @ 6:00 PM

With renovations for a refurbished pool area and new locker rooms underway, the Joseph G. Caputo Community Center will start planning for renovations and upgrades that will vastly improve the use of existing space for a wide range of programming opportunities designed for community members of all ages. Learn what plans are in store and provide your input.

Placemaking & Parking

Placemaking & Parking
June 1, 2023 @ 6:00 PM

We have been listening to the public and businesses and believe that creating more parking spaces that are convenient and accessible to our Downtown will be more supportive of economic development for Ossining. In this public engagement, we want to share some learnings and get public input about the proposed Multi-Modal Transportation Hub and how it will improve parking conditions for current and new uses downtown while encouraging and simplifying getting around Ossining. We will discuss electric mobility alternatives and ways this hub will serve as a prime location for visitors to access Ossining's Downtown attractions, from the Double Arches to the Sing Sing Kill Greenway, the community center, and our lovely shops and restaurants.

Market Square The <3 of Downtown

Market Square- The <3 of Downtown
June 8, 2023 @ 6:00 PM

Market Square is one of the most beloved spaces within the entire Village, and with $2M of DRI funding, it’s about to get even better. Come discuss how you use Market Square today, and how it can be used in the future as an enhanced public gathering space that will support a wide range of activities, including the Farmer’s Market, performances, events, festivals and more. It’s integration with the adjacent mixed-use development at the Post Office Lots and with the Downtown District as a whole will be discussed as well.

Spring on Main Pt. 1- The Possibilities

Spring on Main Pt. 1- The Possibilities
June 22, 2023 @ 6:00 PM

After releasing a Request for Qualifications in mid-2022, Wilder Balter Partners and St. Katherine Group was selected as preferred developer for the Main and Spring Street parking lots, adjacent to the Post Office. After considerable public feedback over the years, the directive was clear: first floor retail and a building reminiscent of the architecture across Main Street. Come hear about the concept taking shape and give your feedback on what you would like to see in this mixed-use housing and commercial development.

Spring on Main Pt. 2- Integrating History with the Future

Spring on Main Pt. 2- Integrating History with the Future
July 13, 2023 @ 6:00 PM

Further discussion regarding the Wilder Balter and St. Katherine Group Development with a focus on architectural design, traffic flow, integration of retail/ commercial space with the existing downtown historic and commercial district and sustainability features.


Return on Investment
July 20, 2023 @ 6:00 PM

What will this cost and how will it impact the taxpayer? Learn how the Village will be maximizing community benefits by leveraging over $21M in grant funding in conjunction with the Village’s Capital Improvement Budget and incentives for private development.

  • Impact on Village Budget (tax implications)
  • Payment in Lieu of Taxes (PILOT) Agreements (creating a win-win)
  • Economic and Community Benefits
  • Project Construction Timetable

let's connect

Let’s Connect!
July 27 @ 6:00 PM

None of this takes place in a vacuum: taking a “zoomed out” approach, let’s discuss how the changes happening downtown will enable residents and visitors to better access the Croton Aqueduct Trail, 200 Main Street, the Community Center, the Croton Avenue business district, and beyond!