Berkshire Money Management Welcomes Financial Paraplanner

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DALTON, Mass. — Berkshire Money Management (BMM), a financial and retirement planning firm with offices in Dalton and Great Barrington, announced that Michael O'Brien has joined the team as a Financial Paraplanner.
 
Most recently, Mike worked in the insurance industry. He has a strong background in client service and financial planning, with experience helping high-net-worth individuals protect their assets and their futures. 
 
He is a licensed Property and Casualty Insurance agent and is currently studying for the Series 65 exam so he can advance into a junior advising role. 
 
At BMM, he is focused on supporting the Director of Financial Planning and learning how to deliver personalized service to the firm's clients.
 
"Success is a team sport," said Natalie Wheeler, Chief Operating Officer at Berkshire Money Management. "We're excited to see Mike bring his talents to the table and grow with us. Stay tuned for updates as he continues to hit the ground running."
 
A lifelong resident of Pittsfield, Mike is a former Mr. Taconic and 2024 graduate of the Berkshire Leadership Program and holds a Bachelor of Arts in Communications with a minor in Spanish from Massachusetts College of Liberal Arts. Outside of work, he enjoys traveling, attending concerts, and spending time with his fiancée and extended family, and stays active with Jiu Jitsu, golf, and cheering on his favorite sports teams.
If you would like to contribute information on this article, contact us at info@iberkshires.com.

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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