View in portrait for best experience

Oliver Cragan

Advisor

CFP®

Oliver has been with The Berry Group since 2013, serving clients in a variety of capacities while bringing strong initiative and commitment to his role as an Advisor. He provides financial advice and investment management to clients, in addition to assisting with daily operational tasks. Oliver became a CERTIFIED FINANCIAL PLANNER® professional in October of 2020. He enjoys challenging himself daily to learn more about the ever-changing world of financial planning.

After graduating from The College of the Holy Cross in 2012, Oliver held a variety of jobs around the country, including serving as a ranch foreman in Wyoming, repairing churches as a steeplejack throughout New England, and exploring the worlds of advertising and software sales in Greater Boston.

Oliver resides in Princeton, MA with his wife and two children. They travel as far and often as possible, but frequent the Adirondack Mountains where they enjoy fishing and hiking.

  • CERTIFIED FINANCIAL PLANNER®

A WEALTH OF INFORMATION

Dive into the latest insights from our expert team with our personal touch.

Independence Without Compromise

Independence Without Compromise

March 18, 2026

By Eric Kittner  Independence Has a Definition Problem, Especially at Scale  I don...

The Vacation Home: More Than A Property

The Vacation Home: More Than A Property

March 9, 2026

By Anna McDonald, Director of Family Learning Family vacation homes have an emotional connection unlik...

Courageous Citizenship and Finding Common Ground

Courageous Citizenship and Finding Common Ground

March 5, 2026

by Deb Dubin, Chief Philanthropy Officer Philanthropy has a role to play in fostering healthy civic di...

Monthly Recap – February 2026

Monthly Recap – February 2026

March 5, 2026

February Observations Volatility Continues on AI Disruption and Geopolitics U.S. equities were mixed i...

VIEW ALL ARTICLES

Let’s make every moment count together…