The story of TRA Group, Inc. begins with a personal experience that revealed a community-wide gap. In 2005, Catherine Wynkoop had hip replacement surgery and found herself unable to drive to her own physical therapy appointments — and equally unable to find suitable transportation options in her largely rural community. That frustration became a conviction: something as simple as a ride to the doctor could be the difference between living independently and losing that independence entirely. In 2011, she co-founded WestFair Rides — the organization known today as TRA Group, Inc. — to ensure that older adults, adults with disabilities, their families, and caregivers have reliable access to transportation and the information they need to live with independence and dignity.
Since then, TRA Group has grown into a multi-program organization with measurable impact. Between 2013 and March 2026, the organization provided 48,749 trips covering 763,441 miles — medical appointments kept, isolation reduced, lives supported. Its Call Center has completed 118,527 calls since 2019, connecting riders to ride coordination, community resources, and its online Resource Hub. And at the core of it all is the Volunteer Program, recruiting and celebrating the drivers whose selfless service makes every journey possible.
Together, these programs reflect TRA Group’s enduring commitment to helping people age in place and lead active, productive lives — no matter their access to transportation.
2010
A Transportation Planning Workgroup formed by Westchester-Fairfield Aging in Place Coalition.
2011
With support from the Helen Andrus Benedict Foundation grant, a steering committee of government and nonprofit partners formed a Board of Directors under the name, Friends of ITNAmerica (Independent Transportation Network America) in Westchester. The first volunteer drivers transport riders to medical appointments.
2012
Friends of ITN in Westchester is renamed WestFair Rides.
2013
WestFair Rides launches a 6-month pilot program with WESTMED in Rye, later expanding to all WESTMED locations. With funding from a Federal Transit Administration Mobility Management grant, service is expanded from Sound Shore to other Westchester locations. WestFair Rides’ volunteer information management platform is shared with At Home on the Sound, promoting the sustainability of ride services in communities.
2014
WestFair Rides hosts its first annual volunteer recognition luncheon, sponsored and hosted by The Ambassador of Scarsdale that year until Covid19.
2015
WestFair Rides expands medical transportation service to cover all of Westchester County. New Rochelle Cares is added to WestFair Rides’ volunteer information management platform.
2016
Successful FTA Triennial Audit
2017
Fundraising program expands with events held at popular Westchester destinations including Crabtree’s Kittle House in Chappaqua, Caramoor in Katonah, and Xaviar’s 20 on Hudson in Yonkers.
2018
WestFair Rides President, Catherine Wynkoop, is invited to serve as member of the national VIS (Volunteers Insurance for Nonprofits) Insurance (formerly CIMA) Advisory Council. Additional agreement to share the volunteer management system with SPRYE which serves Rye and environs.
2019
WestFair Rides is invited by ITNAmerica to become a Trusted Transportation Provider for people with vision disabilities under a grant from Regeneron Pharmaceuticals. Unidos en Transporte is launched in partnership with the United Community Center of Westchester to serve low English-speaking clients. Wynkoop is appointed to the Westchester County Transportation Board and begins meeting with Rockland County Transportation planning group.
Successful FTA Triennial Audit.
All Call Center team AIRS certified as Community Resource Specialists in Aging & Disabilities (CRS-A/D) Three database curators certified CRS-DC.
2020
During the COVID-19 global health crisis, WestFair Rides establishes agreements with 5 backup livery services to ensure fulfillment of all requested medical transportation for WFR clients throughout the pandemic. Technology upgrades link volunteer management and a new information and referral system, enhancing service access for older adult and adults with disabilities in Westchester and Putnam Counties.
2021
WestFair Rides begins a year-long celebration of the organization’s 10th Anniversary. A new development officer shores up fundraising. Two automobiles are purchased to supplement volunteer rides. The Call Center staff doubles and the new information and referral system is implemented. WestFair Rides is renamed TRA, which stands for Transportation, Resources, and Access.
2022
We begin to expand medical transportation service to Greenwich and Stamford Hospitals for Westchester residents and to Westchester appointments for residents of southwest Connecticut.
2025
Began 18 month accreditation process under Inform USA (formerly AIRS).
July 2025, all paid TRA drivers completed PASS (passenger assistance, safety, and sensitivity) certification training by Community Transportation Association of America (ctaa.org).
2026
In early 2026, the closure of the RideConnect and New Rochelle Cares ride programs opened a new chapter for TRA. Moving swiftly and with purpose, TRA welcomed 80 volunteer drivers and 400 registered riders into the fold — offering a seamless transition and a continued promise of reliable, compassionate transportation. This was not a merger, but a commitment: to show up for more neighbors, in more communities, without missing a beat. TRA’s mission remained unchanged, and its reach only grew stronger.
