Bennington Financial Planning Group
Data sourced from SEC public records (and other sources when available). Refreshed weekly • Updated today.
Client AUMClient assets under management
$262,817,077
Clients
376
Advisors
3
of 3 employees
About
Bennington Financial Planning Group provides investment supervisory services and financial planning to individuals, trusts, estates, charitable organizations, businesses, and reported state or municipal government clients. The firm prepares an Investment Policy Statement for each client and manages both discretionary ($267,964,756) and non-discretionary ($13,525,944) assets (figures as of December 31, 2025), while also offering hourly financial planning engagements.
The firm’s investment process is grounded in fundamental analysis, supplemented at times by technical and cyclical analysis, and employs long- and short-term strategies including covered-call writing; it may trade on a discretionary basis when authorized by a client. Accounts are reviewed on a bi-weekly or monthly schedule, and clients are billed through a combination of percentage-of-assets management fees and hourly planning fees, with custodian reporting provided by the recommended broker-dealer’s clearing arrangement.
Distinctive features include that all advisors are dually registered as broker-dealer representatives and the firm recommends an affiliated broker-dealer for custody and trade execution (trades are executed at the brokerage firm’s cost with no commission retained), and advisors split substantial time between the affiliated broker-dealer and the advisory business. The firm also does not permit clients to direct alternative broker-dealers for execution, a practice and client mix that are less common among similarly supported firms and that the brochure discloses as potential sources of conflict.
Client services
Expertise
Fee options
$0 - $500,000: 1.5% annually $500,001 - $1,000,000: 1.25% annually $1,000,001+: 1.0% annually
$225 per hour for financial planning services
Fee-only: $225 per hour for financial planning services
Main office
207 West Main Street
Bennington VT 05201
Advisors at this office
3
Most active in
Florida · Maine · Massachusetts · New Hampshire · New York · North Carolina · Vermont
Disclosures
Exclamation point means they have disclosures of this type. Check mark means no disclosures of this type were found.
Business activities & affiliations
Is active or affiliated with:
Broker-dealer / trader
They provide brokerage services and may earn transaction-based compensation in addition to advisory fees.
Is not active or affiliated with:
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Insurance agent
They sell insurance products and may earn commissions on those sales.
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Bank
They're affiliated with a bank that may offer its own financial products and services.
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Trust company
They provide trust and estate administration services, typically for separate fees.
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Fund sponsor
They manage or sponsor investment funds and may earn management or performance-based fees if clients invest in them.
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Accountant / CPA / tax prep
They offer tax and accounting services, typically for separate fees.
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Lawyer
They provide legal services, typically billed separately.
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Real estate agent
They facilitate real estate transactions and may earn commissions.
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Other specialized services
They may provide services such as pension consulting or municipal advisory work, typically for separate fees.
Advisors at this firm
Michael M
Series 63, Series 66
Bennington, VT
Bennington Financial Planning Group
Michael Mckenna is a financial advisor at Bennington Financial Planning Group with 31 years of industry experience. He holds Series 63 and Series 66 designations and has been with Bennington Financial Planning Group since 1995. In addition to his advisory role, he provides tax preparation services. Bennington Financial Planning Group offers portfolio management and financial planning services to individuals, trusts, estates, charitable organizations, businesses, and government clients. The firm utilizes fundamental analysis complemented by technical and cyclical methods, employing both long- and short-term trading strategies including covered-call writing, and maintains a dual registration structure with an affiliated broker-dealer.
Donald M
CFP®, Series 63
Bennington, VT
Bennington Financial Planning Group
Donald Mckenna is a CFP® with 44 years of industry experience. He has been with Bennington Financial Planning Group since 1995 and is also the president and owner of D.B. Mckenna & Co., Inc., a broker-dealer firm. In addition, he owns a small real estate firm and provides tax preparation services. Bennington Financial Planning Group offers portfolio management and financial planning to individuals, trusts, estates, charitable organizations, businesses, and government clients. The firm uses fundamental analysis supplemented by technical and cyclical analysis, employs both long- and short-term trading strategies including covered-call writing, and maintains a distinctive operational model with an affiliated broker-dealer.
Brian M
CFP®, Series 63, Series 66
Bennington, VT
Bennington Financial Planning Group
Brian McKenna is a CFP® professional with 19 years of industry experience, currently serving as a financial advisor at Bennington Financial Planning Group since 2010. He also maintains a role with D.B. McKenna & Co., Inc., a broker-dealer firm, dedicating half of his time to each business. In addition to his advisory work, McKenna is a member of the Bennington Redevelopment Group LLC, which focuses on revitalizing the downtown Bennington community, and he provides tax preparation services. Bennington Financial Planning Group offers portfolio management and financial planning services to individuals, trusts, estates, charitable organizations, businesses, and government clients. The firm employs a fundamental analysis approach supplemented by technical and cyclical methods, utilizing both long- and short-term trading strategies including covered-call writing, with accounts reviewed regularly and discretionary management available.
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