First-Time Sleepaway Camp for Boys: The Winaukee Mainland Experience

Ready for the Jump? A Parent’s Guide to Your Son’s First Summer at Winaukee

February 10, 2026

The decision to send your son to sleepaway camp for the first time is a milestone moment, for him and for you. We know the questions that run through a parent’s mind: Will he make friends? Who will help him if he loses a sock? Is he ready for this?

At Camp Winaukee, we’ve spent decades perfecting the “First Summer” experience.

We don’t just welcome your son to camp; we welcome him into a brotherhood specifically designed to help him find his footing, grow his confidence, and discover who he is.

The Mainland: A Specialized World for Younger Boys

One of the most unique aspects of Winaukee is our Mainland campus, dedicated entirely to our younger campers (ages 7–12). This isn’t just a separate location; it’s a tailored environment where the pace, the coaching, and the supervision are all dialed in to meet the needs of boys at this specific stage of development.

On the Mainland, “trying something new” is the gold standard. Whether it’s their first time on a waterski or their first time sleeping away from home, the environment is intentionally supportive.

The Support System: Mentorship Over Management

We believe the quality of a camper’s summer is directly tied to the quality of his counselors. Our staff aren’t just supervisors; they are “big brothers.”

The Cabin Dynamic: Our counselors live in the bunks with the boys, facilitating everything from morning cleanup to bedtime “highs and lows” of the day.

Hands-On Guidance: From reminding them to put on sunscreen to helping navigate a social disagreement, our staff is trained to provide the “scaffolding” that helps boys become more independent.

Building Confidence Through Connection

The first summer is about “small wins.” It’s about the first time he hits a bullseye in archery or the first time he performs a skit in front of the camp. These moments are amplified by the culture of the Winaukee brotherhood. On the Mainland, we celebrate the effort as much as the outcome.

When your son realizes he can thrive in a new environment, navigate a schedule, and forge his own friendships, he returns home standing just a little bit taller.

Partnerships with Parents

We know that “sending him off” is a partnership. From our communication throughout the summer to our careful placement of boys in bunks, we are committed to making sure you feel as connected to the experience as he is.

Your son’s first summer at Winaukee isn’t just a trip to New Hampshire, it’s the beginning of a journey he’ll carry with him for the rest of his life.

Ashleigh Jackowitz

Ashleigh grew up in Boise, Idaho and got her first taste of sleepaway camp in 2006 when she was hired to work on the waterfront at Camp Walt Whitman. She spent 5 summers there before joining the full-time team. Ashleigh attended Williamette University in Salem, Oregon as a college athlete in Volleyball. Prior to starting full time in camping, she took the chance to travel around the world, to every continent, over the course of 3 years. Teaching English in South Korea for a year was definitely a highlight! She has been involved with the American Camp Association as a Tri-State Conference Program Track Chair and is a speaker at multiple camp conferences. She also is a passionate advocate of Project Morry, an organization that helps youth from under-served communities attend summer camp, having served for many years on their Dare to Dream Committee. Her favorite role is as mom to their sons Cooper & Henry. Ashleigh, Matt, Cooper & Henry currently live in Ridgefield, CT.