Most of my readers know how much our family appreciates and values attending our annual family retreat hosted by my father-in-law, Walter Weinstein. For five days, sons, daughters, spouses, children, grandchildren, and now great grandchildren gather at the Woodloch Pines Resort in Eastern PA for shared meals, birthday celebrations, and enough activities to delight and entertain the diverse crowd.

I have written about the positive impact of this reunion multiple times over the years. But I remember that my second most popular newsletter (the first being my remembrances of my mother after she died) was the one where I first wrote about this annual gathering: The Best Way to Spend Your Money ― PayTaxesLater.com/The-Best-Way-to-Spend-Your-Money.

Maintaining and strengthening these extended family relationships is particularly meaningful for me. Many of our daughter Erica’s friends deserted her after learning of her disability. But these annual gatherings cement her place in the Weinstein clan. Cindy and I love seeing her at these gatherings—it can be difficult to arrange time to see your grown children—but we also love seeing the cousins establish bonds of friendship and support. I know family will always love and help take care of Erica even after Cindy and I pass.

But what was most extraordinary about this year’s gathering were the plans we hatched to continue this annual tradition after Walter passes. That is the strongest testament to the value of his generosity and insight and will cement his family legacy.

None of us can afford to sponsor 29 individuals for five days at a fancy resort. The newly hatched plan that received unanimous approval is to continue the family gatherings in more modest venues. We are already looking at renting one or more Airbnbs or VRBOs not far from Cindy’s brother’s house.

I will happily report that many more clients are telling me of their plans for family gatherings funded by Grandpa or Grandma (or both). I do hope some of those decisions have been inspired by Walter’s example. That said, the biggest challenge is gathering the entire family together in the face of other family and work commitments. What has worked for us is scheduling the gathering in the same week every year so everyone has notice and can plan. It really helps that we all love this event and give it priority.

One way you might improve attendance is to mention to your family that you are updating your wills and trusts and that it is important to you that the entire family makes it to the family gathering.