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125 Years of Community – Northern Neck Celebration

Group of employees with mascot at company event

May 2025 After our 124th Shareholders meeting in April, we kicked off our 125th Anniversary celebration right where it all began—Irvington, Virginia. For a quarter past a century, we’ve been helping customers float their dreams, secure their first homes, and experience banking that goes beyond transactions. This Northern Neck Community event was a true celebration […]

Quarterly Commentary Q2 2024

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Market Overview The topic of interest rate cuts continues to dominate the financial markets. Investors are focused on when the Federal Reserve will lower rates, while also keeping a close eye on corporate earnings. Economists are analyzing inflation and labor market data to determine their impact on the probability and timing of rate cuts. Comments […]

Making a Difference Through Partnership and a Financial Bootcamp with Southside Community Development and Housing Corporation

Chesapeake Bank and Southside Community Development and Housing Corporation (SCDHC) partner to bring a financial bootcamp and incentive to eight individuals in Richmond. SCDHC provides residential and commercial development, as well as homeownership, financial education and counseling, employment services, and other support programs to low-income families throughout central Virginia. Most recently they have partnered with […]

Quarterly Commentary Q1 2024

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Market Overview Global equity markets got off to a promising start during the first quarter. While the S&P 500 led all broad market measures, the gains were generally across the board including all styles (growth/value), market capitalizations, and geographical regions. Building on strong performance from the fourth quarter of 2023, the three U.S. large-cap indices […]

Quarterly Commentary

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Market Overview As the second quarter came to a close and we entered into the third quarter, markets continued their upward trajectory as the S&P 500 rose to its highest level since March 2022. Unfortunately, this trajectory proved unsustainable as rising global bond yields, mixed inflation data, and concerns over a future economic slowdown weighed […]

Chesapeake Wealth Management Celebrates 50 Years of Service

Chesapeake Wealth Management logo

Chesapeake Wealth Management (CWM), a sister company to Chesapeake Bank, marks a milestone anniversary this year. Founded in 1973 as the Northern Neck’s first-ever trust company at Chesapeake National Bank, CWM has evolved over 50 years into a thriving, holistic wealth management company with a dedicated, community-minded team of experienced wealth advisors, portfolio managers and […]

A Message from our Chairman, CEO and President, Jeff Szyperski

A message from the chairman

Jeff Szyperski, the Chairman, CEO and President of Chesapeake Financial Shares, Inc., shares some thoughts on the strength and soundness of Chesapeake Bank, and why this will continue. Hello, I’m Jeff Szyperski, President and CEO of Chesapeake Bank. I know there’s no dearth out there now of analysis of the Silicon [Valley] Bank failure and […]

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