Jenny Crittenden, Executive Director of Gloucester’s Main Street Preservation Trust, will become the Senior Vice President of Retail Alliance in Norfolk, effective Jan. 3, 2022.

Crittenden spent nearly 16 years at the Gloucester nonprofit, growing what was once a fledging startup organization into a national model for downtown revitalization. She also served as part-time Director for the Cook Foundation, a nonprofit with a mission to nurture the arts in the community.

The Main Street Preservation Trust and Cook Foundation will hire separate executive directors to fill Crittenden’s roles.

“I will still work with Gloucester, but it will be from a regional level,” Crittenden said. “I’ve had the pleasure of supporting our Main Street businesses through my work at the Trust and excited to be able to extend support now to all Gloucester retailers through my next role.”

Gloucester’s Main Street Preservation Trust has long been a member of Retail Alliance, which serves the interests of local retailers in Hampton Roads by promoting and supporting the growth of retail businesses and trade through signature programs, including educational workshops, member programs and lobbying efforts.

Crittenden joined the Main Street Preservation Trust in March 2006, roughly 13 months after its inception.

“When I first came on board, I was handed four file boxes and brought my own chair to my office,” Crittenden said. “I knew a few business owners downtown but not many. Today, we’re a nationally accredited Main Street. We’ve been bestowed awards at the state and national levels for programs and projects I’ve had the pleasure to lead.  I am grateful for the experiences had and the people I’ve met. I am also grateful for the board members under which I served.  I have learned a lot from those around me.”

Under Crittenden’s direction, the Main Street Preservation Trust attracted additional business to the Gloucester Village and enhanced the economic and business environment by supporting the Gloucester Main Street Association, all while preserving the historical landmarks in the Gloucester Courthouse area.

The Main Street Preservation Trust launched several grant programs over the years to support entrepreneurs but a stand out grant award given to the organization was $100,000 by the Virginia Department of Housing & Community Development to be a pilot community (only 3 in the state) under the Governor’s Community Business Launch Program that she titled “Launch Gloucester,” a competition that resulted in six new businesses opening in 2015.

Today Main Street attracts locals and tourists to its picturesque village full of unique shops that include bakeries, boutiques, a massage and wellness clinic, retail outlets and distinctive restaurants. Gloucester Main Street achieved national accreditation by the National Main Street Center in 2017.

Nearly every business owner along the Main Street corridor is on a first-name basis with Crittenden.

Gary Ward, owner of the restaurant Olivia’s in the Village as well as Scoot’s BBQ in Gloucester Point, is appreciative of all the work she has done on behalf of the community.

“I got to see firsthand the difference she made,” said Ward, who opened Olivia’s in the Village in 2005. “For me to watch Main Street evolve and grow has been pretty incredible. The vision with the Main Street Preservation Trust was to preserve Main Street, and clearly she was the person to execute that vision. Jenny’s so proactive and such a go-getter. We were lucky to have her for so long.”

During the COVID-19 pandemic, Gov. Ralph Northam appointed Crittenden to represent small brick and mortar retail on the Governor’s Small Business Task Force. Crittenden earned a Main Street Forward Award at the national level for her recovery and resiliency efforts, including the development of an e-commerce platform – Downtown Dollars – to help Main Street business owners stay afloat.

Crittenden also served as the marketing and sponsorship chairs for the Gloucester Arts Festival, an event that dates back to 2017 that quickly grew from a week-long festival into a month-long celebration held every June.

As part-time director of the Cook Foundation, Crittenden spearheaded the efforts to paint the “Life & Legend of Pocahontas” mural at the Gloucester Library. The tribute to the favored daughter of Chief Powhatan is one of four mural projects she led in the Gloucester Village commissioned by the Cook Foundation, the latest of which celebrates the life and legacy of T.C. Walker.

The nonprofit is behind the annual outdoor Virginia Symphony performance, Main Street Flower Baskets and several theater productions and scholarships to benefit and diversify the arts in Gloucester.

Crittenden will move to the Ghent section of Norfolk later this month. The Main Street Preservation Trust and the Cook Foundation anticipates hiring for the vacant positions in November so Crittenden can help with the transition.

“I will miss the business owners, many whom I now call friends,” Crittenden said. “There has already been tears shed with some because I’ve grown so close with them on their journeys in business and in life.  Main Street isn’t just about the businesses but it’s the people and I will miss them the most.”

While Crittenden’s address will change, her heart will always be a part of Gloucester.

“When I look back on my almost 16 years here in Gloucester, I can’t help but smile. I smile for the experience I’ve had and the people I’ve met and am proud of the work we’ve accomplished together.”

“I’m excited to take the skillset I’ve developed and the amazing lessons I have learned working in downtown revitalization with entrepreneurs and applying that in my new role as Senior Vice President of Retail Alliance but I know I’m leaving a piece of me behind here in Gloucester.”

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