Talking Legacy: How to Start the Conversation About Your Woods

Summer brings families together on the land. Maybe it’s a shared cabin by the lake, a hike through the family woods, or picking berries with your grandchildren in a sunny clearing. It’s a time for connection and stories—and, if you’re a woodland owner, it might also be the right moment to begin one of the most important conversations your family will ever have:

What will happen to the land after you?

Legacy planning can feel overwhelming, emotional—even a little daunting. But it’s not just about paperwork. It’s about sharing your connection to the land and helping your family build their own. It’s about relationships: with the woods, and with one another.

Summer, with its gatherings and slower pace, offers a natural opportunity to begin that conversation.

Here are a few ways to open the door:

1. Start with the stories.

Legacy planning doesn’t have to begin with lawyers or paperwork. It can begin with a simple walk through the woods. Invite a family member to join you. Share what you’ve done on the land—planting trees, harvesting timber, building trails. Talk about what it means to you.

Stories are powerful. They invite your family into your connection with the land—and help them see its value in a whole new way.

 2. Name your hopes.

Many landowners are clear about what they don’t want—like subdivision, conflict, or development—but haven’t said out loud what they do want.

Take a moment this summer to share your vision. “I hope this land stays intact and healthy—and that you all feel a part of it.” When your family hears this directly from you, it creates clarity and can guide future decisions.

 3. Make space for questions and emotions.

Legacy conversations can stir up a lot—grief, uncertainty, even tension. Your kids or relatives may have questions you’ve never thought to answer:

• “Can we afford to keep the land?”

• “Would we have to manage it ourselves?”

• “What happens if we don’t agree?”

You don’t need to have every answer. But making space for honest conversations now can prevent heartache later.

4. Talk about next steps—and write them down.

If you haven’t already, now’s a great time to:

• Identify your goals for the land

• Review or create a forest management plan

• Talk with your consulting forester

• Learn about legal tools like wills, trusts, or conservation easements

• Write a legacy letter to the next generation

Even a simple letter can be a powerful gift—to you and to those who will carry your care forward.

5. You’re not alone.

You don’t have to figure this out on your own. Vermont Woodlands Association is here to help. We can connect you with professionals—foresters, estate planners, conservation experts—and provide tools to guide your next steps.

This summer, as your family gathers on the land, take some time to begin the conversation. It doesn’t have to be formal or final. Just start.

Because the best legacy isn’t just land. It’s connection, care, and a shared commitment to the future of your woods.

Have you started your legacy conversation?

We’d love to hear your story. Email Kate Forrer at director@vermontwoodlands.org to share your woodland legacy journey or get assistance.