The Stride Family Enterprise Retreat

The Family Enterprise Retreat is Stride Family Business Alliance’s annual multi-day gathering of family businesses — three days away from the office where owners, next-generation leaders, and the people who work alongside them have the conversations family enterprises rarely get to have out loud. The first retreat took place in 2025; the second was held September 8–10, 2026, at The Prospect Berkshires in Egremont, Massachusetts.

Stride 2026 Family Enterprise Retreat group photo at The Prospect Berkshires — The 2026 retreat at The Prospect Berkshires, Egremont, Massachusetts.

The 2026 retreat at a glance

When: Tuesday, September 8 – Thursday, September 10, 2026
Where: The Prospect Berkshires, Egremont, Massachusetts, with an offsite dinner at The Red Lion Inn in Stockbridge
Format: Tuesday arrivals, a family-style welcome dinner, trivia night led by Corey Finkle, and a bonfire; Wednesday a full day of sessions and intergenerational conversation; Thursday a sunrise hike, sessions on succession and mentorship, and a closing lunch
Program: a dozen speakers, almost all members and friends of the community sharing what they have actually lived

Sessions and speakers in 2026

Sarah Eustis on the methodical succession she led with Cambridge Family Enterprise Group in the early 2000s.
Adam S. Karofsky and David M. Karofsky, a father-and-son duo from The Family Business Consulting Group, who facilitated a session and joined all three days.
Amy Born and Allison Chisolm on the next phase of your life and your role in the family enterprise.
Christopher Walrath and Jonathan Phillips on mentorship across generations.
Lisa Manning, Kurt Hudson, and CJ Fraser on how EOS helped their families through succession.
James Murphy on how members can think about financially transitioning their business.
Rosie DeFilippo on how Stride has shaped her family’s succession planning.

Founder Jason Packer opened the retreat with a talk on why evolution favors multigenerational families — the grandmother hypothesis, Darwin’s “descent with modification,” and three questions for every family enterprise. Read Why Do Grandmothers Exist?

Attendees gather by the lake at dusk at The Prospect Berkshires

Sponsors and supporters

The 2026 retreat was made possible by fifteen sponsors, most of them members of the community: Farrell Fritz, P.C., Stride’s year-round partner and the retreat’s underwriter; Morgan Stanley, host of the Red Lion Inn dinner; CFAR Consulting and Coaching; Beacon Bank; Belden Hill Partners; Captains Club; The Family Business Consulting Group; BanyanGlobal Family Business Advisors; Lisa Manning of EOS Worldwide; Choice Words; Fraser Engineering; LC Anderson; and three member families — Albany Management, Phillips Hardware, and Walrath Recruiting — who helped organize the retreat with their own hands.

What attendees said

It was thoughtfully orchestrated … well done! It is always a pleasure to meet good, hard-working people, and I am thankful for the experience. The location was perfect to slow down and really listen to everyone.
Karen E. Laberge, President, Albany Management, Inc.

What’s next: 2027

The 2027 retreat will be a new concept, built with the community rather than for it. Stride is forming a 2027 Retreat Planning Committee of members who want a hand in shaping the format, the place, and the conversations. To join it, email Jason Packer at jpacker@stridefba.com.

Attendees listening during a session at the 2026 Stride Family Enterprise Retreat

Attending the retreat

The retreat is open to Stride member families and invited friends of the community, and both memberships include discounted retreat tickets. Read the full 2026 retreat recap, learn about Membership, or get in touch to ask about 2027.