September 8–10, 2026 · The Prospect Berkshires, Egremont, MA
The Stride 2026 retreat exceeded all expectations. The families who joined us spent three days together in the Berkshires having the kind of natural, open conversations about ownership, leadership, and family that most family enterprises never get to have out loud — in a comfortable, safe setting, with people who understand exactly what it takes.
This community is developing, growing, and gelling in a way that is allowing families to have natural, open, strategic, ownership, leadership, and family conversations in a comfortable, safe setting. I’m excited to see how this can continue to connect family businesses.
Jason Packer, Founder, Stride
Three days in the Berkshires
Tuesday opened with arrivals, a family-style welcome dinner, and a trivia night led by Corey Finkle that broke the ice fast, followed by a bonfire under the stars. Wednesday was a full day of sessions and intergenerational conversation, capped by an offsite dinner at The Red Lion Inn, where Timothy Eustis’s team led a tour of one of the true treasures of the Berkshires — it felt like walking through a museum, with guests over the years ranging from Franklin Roosevelt to Jay-Z to Oprah. Thursday brought a sunrise hike, our sessions on succession and mentorship, and a closing lunch.
Sessions and speakers
The program was built almost entirely by members and friends of the community sharing what they have actually lived. Our deep thanks to each of them:
- Sarah Eustis shared the methodical, remarkably smooth succession she led with the help of Cambridge Family Enterprise Group (CFEG) in the early 2000s — a process that has given her family tremendous clarity and success in the enterprise ever since.
- Adam S. Karofsky and David M. Karofsky, a father-and-son duo, helped facilitate a great session and joined us for all three days.
- Amy Born and Allison Chisolm facilitated a wonderful session on the next phase of your life and your role in the family enterprise.
- Christopher Walrath and Jonathan Phillips led our session on mentorship.
- Lisa Manning, Kurt Hudson, and CJ Fraser showed how EOS Worldwide helped their families through the succession process.
- James Murphy shared how Stride members can think about financially transitioning their business.
- Rosie DeFilippo shared with the community how Stride has been impactful to her family’s succession planning.
- Corey Finkle led trivia night on the front end of the retreat — and had the whole room laughing within minutes.
Thank you
To the families who made the time together so special: Reneé Walrath, Christopher Walrath, Tyler Phillips, Jonathan Phillips, Rosie DeFilippo, Karen Laberge, CJ Fraser, Nancy Fraser, Kurt Hudson, Ryan B. Ellis, and Anne Putnam.
To The Prospect Berkshires for the most stunning space, outstanding service, delicious family-style food, and comfortable accommodations.
To Farrell Fritz, P.C. for underwriting our event, and to John Malicki and Martha Cordo for sponsoring, joining us, and offering the community their expertise in family wealth planning.
To our sponsors and supporters: Beacon Bank, CFAR: Consulting and Coaching, Belden Hill Partners, BanyanGlobal Family Business Advisors, and Daniel Cheetham.
If we left anyone out, our deep apologies — everyone in the room contributed greatly to the experience.
What’s next: 2027
Next year’s retreat will be a whole new concept, and we’re building it with the community rather than for it. We are forming a 2027 Retreat Planning Committee — members who want a hand in shaping the format, the place, and the conversations. If this year moved something for you, this is the way to pay it forward.
Reach out to join the planning committee →
And as always: what is shared in Stride stays in Stride.
