Outdoor Education

The Next Great Adventure: College Drop Off

By Tom Holland September 16, 2025
Sunset behind pine trees.

Each summer, our staff training ends with a final circle. I give our trip leaders a few last words-some inspiring (“Seize the day!”), some practical (“Don’t forget to check the tire pressure!”). Then we hand out flight plans and van keys, and off they go. In that quiet time after they leave, Catherine and I sit together, proud and tired, knowing that over the two weeks of staff training, we gave them what they need to succeed on their summer adventure. They are ready and have all the tools needed to thrive in their summer of adventure. 

This past weekend felt the same. We took Mads (our oldest daughter) to college. The emotions are all mixed together-pride, apprehension, sadness to see our girl leaving home, excitement to have her walk through this great door of life. But at the core is the same truth: she is ready.

Tom Holland walking with his daughter, Mads, to college drop off.

She is ready because of the formula we believed in as parents: creating opportunities for her to step out into the world on her own. Part of that was sending her on Wilderness Adventures trips. Out there she learned to pack and organize her gear, to push through rain and homesickness, to make friends from all over, to trust leaders, and eventually to become a leader herself. She gained confidence with every mile on the trail, and so did we, learning to let go, bit by bit. Learning to allow her to be the driver and the decision maker of her life. It has not always been easy, but, as we shared with Mads the other day, she has all the tools she needs for this next step. 

Not every parent feels ready when the time comes to drop their child off at college. And not every child feels ready, either. But experiences like camp, like WA, prepare both sides of the equation. They give kids the resilience to face challenges, and they give parents the trust to step back. Without those “practice runs,” this moment can feel overwhelming. With them, it feels like a natural (albeit emotional) next step.

A common thing I hear from parents considering WA is, “I don’t think I can let them go.” I understand that feeling. But my encouragement is this: you should. Both for them and for you. Because sooner or later, the moment will come when you have to. And it is so much easier when you know that both you and your child are ready.

So yes, Catherine and I drove away from college drop-off in tears… but we also drove away grateful. Grateful for the path that got us here, grateful for the confidence Mads carries with her, and grateful for the knowledge that she is stepping into her greatest adventure yet.

Here’s to her greatest adventure ahead. 

****

As we let her go on her next big adventure, I feel the same way I did when we sent her to camp for the first time. 7 Years ago, in July of 2018, I wrote this as Mads returned from her first ever WA trip:

You all know I talk a lot about summer camp. Most often in my life, I have talked about its impact on children in general (American children, camp participants, and camp alums). Most times, I am using research to share its impacts, or I am using anecdotes from my years of teaching and camp directing, or I am thinking about my own camp experience as a teenager on Wilderness Adventures. But this is different. Yesterday our kid, Mads, returned from 2 weeks of camp with Wilderness Adventures (shout out second generation camper!), and to hear the thrill in her voice recounting the adventure was truly a gift. 

Obviously, Catherine and I could have peered into her experience in the Adirondacks at any moment to check on her, but we didn’t (and it was tough), seeking to allow her to have this experience without mom and dad’s presence being felt. And from the moment she ran out of gate D1, something was a touch different, changing my perception of camp altogether. 

Maybe it was the way she told me to step aside as she grabbed her bag from baggage claim and did not need any help carrying it to the car. Or maybe it was the way she told me of her new friends from all over and what their favorite meals were, and recounted inside jokes that I will never understand (and that’s fine). Or maybe it was the way she spoke of her trip leaders as people she wanted to be like when she was older both in their character and how they speak with funny accents sometimes. It could be her telling me with laughter of the challenges she overcame like homesickness, rain, not packing enough shorts or losing some of her gear. Or maybe it was the way she turned my iTunes to Michael Jackson’s ‘Man in the Mirror’ and sang it as loud as she could (afterwards she said “Dad, you do know who Michael Jackson is, right?”) 

She spent 2 weeks soaring, and setting aside all my roles I have had in the world of summer camp, I sat there as a proud father smiling and thinking, “Small victory for C & T in the parenting category this summer, and an even bigger win for our sweet Mads.”

I could not be more grateful. 

A special thanks to the institution of camp for the magic you create, and to Mads’ leaders who made that magic come to life.