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From our founding in 1900 to our expansion into Williamsburg in the mid-1990s, Chesapeake Bank has grown alongside the communities we serve, building a legacy of trust, service, and connection—one shaped by amazing folks who make this community truly one-of-a-kind. This year, we proudly celebrate 125 years of innovation, growth, and shared success. “The few. The proud. The still-standing community banks. We’re one of them, and we’re proud of that,” said Jeff Szyperski, Chairmen, CEO, President.
Our recent anniversary celebration in Williamsburg was more than just a gathering— it was a sincere nod to the customers, employees, and neighbors who’ve helped shape our journey here.
A Legacy of Commitment with Community at Its Heart
Our Williamsburg story began with a supermarket branch, along with ATMs at the iconic Williamsburg Pottery. In 1996, we opened our freestanding branch at Five Forks, marking a new chapter in our commitment to serving James City County and beyond.
Since then, we have grown to a total of nine retail branches, support buildings, and business offices—standing alongside the Williamsburg community and supporting the local businesses, families, and organizations that make our town thrive. Through innovation, dedication, and a strong foundation of values, we have grown into something much bigger than just a business—we have become a family.
“I have developed a relationship with all these people at this bank. They have been so responsive and been excellent people to work with,” says loyal customer, Steve T. of The Drying Co.
We are proud of our continued growth in the Williamsburg region, thanks to our customers, neighbors, and teammates. Whether it was a shared memory of dodging hail across the parking lot and spotting a rainbow over Richmond Road or simply a moment of connection, the event reminded us that this milestone isn’t just about our organization—it’s about everyone who has contributed to our success.
Thanks to Williamsburg Radio Station AM 740 Williamsburg, Smallcakes Williamsburg, Virginia Finest Chocolate, Old City Barbeque and the Virginia Beer Company for being a part of the party. We had some delicious bites and proudly rolled out The Chesapeake Way Hazy IPA, crafted in collaboration with VBC. Cheers to our amazing journey!
Looking Ahead, Together
Leigh Houghland, EVP Williamsburg Regional Executive and Senior Lender highlighted the importance of being a local, independent community bank, stating, “We can make quick decisions for our clients, and we can support our community.” As we move forward, we remain committed to independent banking and serving this community with the same dedication we’ve shown for a quarter past a century.
The partnerships, friendships, and support we’ve gathered over the years inspire us to keep growing, innovating, and working with the wonderful folks of Williamsburg.
“I feel blessed to be here and work with some great teammates and great customers. Thank you for recognizing this huge milestone. It’s BIG,” said Houghland.
