B

Bennington Financial Planning Group

Updated today

Client assets under management

$262,817,077

Clients

376

32% high-net-worth

Advisors

3

of 3 employees

Firm type

Supported

1-4 advisors or >$200M in AUM

Clients per advisor

125

Very High

Average account size

$698,982

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

Financial planning Portfolio management

Expertise

College savings (529s, UTMA, etc.)

Want help finding the right advisor?

Answer a few questions to see advisors matched to you.

Fee options

Percentage

$0 - $500,000: 1.5% annually $500,001 - $1,000,000: 1.25% annually $1,000,001+: 1.0% annually

Project-based

$225 per hour for financial planning services

Other

Fee-only: $225 per hour for financial planning services

Main office location

Bennington Financial Planning Group

207 West Main Street

Bennington VT 05201, United States

Number of offices

1

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

Quick links

Advisors at this firm

user avatar

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.

College savings (529s, UTMA, etc.)
user avatar

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.

College savings (529s, UTMA, etc.)
user avatar

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.

College savings (529s, UTMA, etc.)
Warmer team member

Not sure where to start?

We'll help you think it through — whether you ultimately need an advisor or not.

Warmer helps you compare advisors clearly — so you can choose with confidence.

Find your advisor
Discover

Compare top advisor firms by metric, firm size, and location.

Warmer provides personalized recommendations and introductions to independent fiduciary advisors. We do not supervise advisors, manage or hold assets, guarantee performance, or provide advice about specific investments.

Each advisor listed on our site is an independent fiduciary responsible for their own advice. Warmer may receive fees from advisors for participation or referrals; these fees are paid by advisors and do not affect the fees clients pay for advisory services.

For advisor listings, we rely on sources including public filings and data provided by advisors, and we cannot guarantee that all information is current or accurate. Please review an advisor's Form ADV and do your own diligence before entering into an advisory relationship.

By using our service, you agree to Warmer's Terms of Service and Advisory Agreement and Privacy Policy. Logos provided by Logo.dev

© 2026 Warmer Holdings Inc. ("Warmer")