Building Stronger Communities Through Connection and Growth:

At Winning Ways, we transform lives through The Winning Circle Series™ — a trauma-informed initiative offering financial literacy, digital skills, employment training, and expressive arts. Our core programs include Spit and Paint™, Money Talk™, Empower Your Employment™, and Basic Needs Support — all designed to foster healing, build confidence, and support long-term success.

Whether you're rebuilding after hardship or looking to grow, we provide the tools to take your next step — with dignity, creativity, and community.

More About Us

Empowering change in Connecticut

Transform lives with Winning Ways Inc, supporting successful reentry and recovery journeys in Connecticut communities.

At Winning Ways Inc., we serve underserved communities across the state of Connecticut through holistic, trauma-informed programs that promote healing, resilience, and opportunity. Our mission is to transform lives by connecting individuals and families to vital resources, peer-led support, and pathways for personal and professional growth. Through a community-driven approach, we foster sustainable progress and long-term success — paving the way to a brighter, more equitable future for all

Data-Driven Change

Impact in Connecticut: See the Stats

Empowering lives in Connecticut: Explore how our programs foster recovery and reduce recidivism through comprehensive support.

Healing & Empowerment Programs

Our Healing & Empowerment Programs support individuals impacted by incarceration, trauma, and recovery through creative and therapeutic approaches. Services include Spit and Paint™, peer-led support groups, and family healing resources that promote emotional wellness, self-expression, and long-term healing.

Financial Empowerment & Stability

The Financial Empowerment & Stability initiative equips participants with tools to take control of their financial futures. Through Money Talk™, one-on-one counseling, and recovery-focused financial education, individuals gain critical knowledge in budgeting, banking access, and long-term wealth-building strategies.

Employment & Educational Access

Our Employment & Educational Access programming prepares individuals for success through Empower Your Employment™, digital literacy, and career development workshops. These services help participants build confidence, learn marketable skills, and access meaningful employment opportunities.

Community Connection & Navigation

The Community Connection & Navigation program provides essential support with basic needs, housing referrals, reentry resources, and family stabilization. Participants receive guidance navigating systems and services to help them reintegrate, restore relationships, and thrive within their communities.

Bridging Recovery

Building Bridges to New Beginnings

Empowering transformation and successful reintegration for former inmates in Connecticut through supportive recovery and growth programs.

Reintegration Support Program

Empowering individuals to successfully reintegrate into society after incarceration with tailored guidance.

Support Group Offering Comfort and Encouragement in Session.

Addiction Recovery Workshops

Providing targeted workshops to support recovery from addiction and promote lifelong sobriety.

Businessman looking at job search website on a laptop computer.

Job Training and Placement

Offering vocational training and job placement assistance to foster economic independence.

Family Reunification Services

Helping rebuild family connections post-incarceration through counseling and mediation services.