Berkshire Money Management Promotes President, Chief Operating Officer

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DALTON, Mass. — Berkshire Money Management (BMM), a financial and retirement planning firm with offices in Dalton and Great Barrington, announced the promotion of Natalie Wheeler to President and Chief Operating Officer. 
 
"I'm honored and excited to step into this expanded role," said Natalie Wheeler. "Working alongside Allen and Stacey, leaders who truly embody dedication to our clients and community inspires me every day. I look forward to supporting our team and clients as we continue to grow while staying grounded in the values that make BMM special."
 
Natalie has served as BMM's Chief Operating Officer since 2021.
 
In her expanded role, Natalie will continue to lead the firm's day-to-day operations while taking on additional strategic responsibilities. She will work closely with CEO Allen Harris and Co-owner and Chief Engagement Officer Stacey Carver.
 
"Natalie has been the quiet force behind so much of our success," said Allen Harris, CEO and Chief Investment Officer of Berkshire Money Management. "Her promotion to President is both a recognition of the leadership she's already shown and a strategic move for the future of our firm. With Natalie in this role, I'm more confident than ever in where we're headed—and in how we'll get there."
 
Before joining BMM, Natalie spent nearly a decade as Director of Office Operations at another financial firm, where she earned a reputation as a savvy and effective leader. She holds a bachelor's degree in criminal justice and law enforcement from Southern Vermont College.
 
Natalie lives in Southern Vermont with her children, Tre and Gianna, and her two dogs, Sofia and Clover. Outside of work, she enjoys coaching youth sports, golfing, bow hunting, and is a proud member of the American Legion Auxiliary Post 29.

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Bell, Ogle Win at May Day Race in Dalton

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DALTON, Mass. -- Stefan Ogle was the top male 5-kilometer finisher and Lindley Bell the top female 5K finisher at the 2026 Community Recreation Association May Day Races on Sunday at Nessacus Middle School.
 
Ogle’s winning 5K time was 19 minutes, 7 seconds, Brady Payson was second in 19:41, and Lake Kittler third in 19:43. Bell’s winning women’s time was 23:56, followed by Kristy MacWilliams in 24:22 and Chelsea Smith in 29:20.
 
Girls led the Splatter Sprint mile race, with Payton Anastasio, age 11, the top overall finisher in in 8:07, 12-year-old Breelin Touponce second in 8:44 and 11-year-old Brooklyn Renderer third in 8:45. The top three boys were Jace Esposito in 8:54, Michael Londergan in 10:15 and Samuel King in 10:38.
 
In the kids’ Obstacles & Popsicles half-mile race for ages 6-8, 7-year-old Henry King was first in 4:00, 8-year-old Jake Vosburgh finished second in 4:01, while 7-year-old Maisey Reed was third in 4:31. Evan Vreeland was third among the boys in 4:41, while Cecelia Polson was the second-place girl in 4:37 and Harper Phelps was third in 4:40.
 
In the 5-and-under race, Jack Barbour was first among the boys in 4:38, Jackson Lavierdiere was second in 5:05, and Mae Cimini third in 5:10. Kennedy Phelps was the top girl in 5:14, while Laura Vosburgh was second in 5:57 and Olivia Shea third 5:58. 
 
5K Race
1. Stefan Ogle, 19:07. 2. Brady Payson, 19:41. 3. Lake Kittler, 19:43. 4. Brian Ducey, 19:46. 5. Chaz Mahar, 21:35. 6. Philip Malm, 21:50. 7. Benjamin Ward, 22:48. 8. Bret Matthews, 23:11. 9. Robert King, 23:28. 10. Noah Aldrich, 23:50.
 
Kids' Splatter Sprint 1 Mile Race
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