Northwest Connecticut has one of the highest concentrations of private and boarding schools in the country. Every school year, parents drive in from New York, Boston, and around the world for move-in day, family weekend, games, and graduation. A lot of those visits leave a free afternoon and a student who doesn't want to sit in a restaurant. More and more of those families spend it on the water with us. Here's why, and how to plan a lake day around a school visit.
Our dock on Lake Lillinonah in New Milford is a short drive from many of the region's private schools. A two- or three-hour captained charter makes a school visit feel like a real family day: a fall foliage cruise on parents' weekend, tubing with your student's friends, or a graduation celebration on the lake. No boat or license needed.
The private schools around us
The Litchfield Hills and the towns around Candlewood Lake have been home to independent schools for well over a century. Within roughly 45 minutes of our dock, families visit schools like:
- Canterbury School in New Milford, minutes from the lake
- The Frederick Gunn School and Rumsey Hall School in Washington
- Kent School, South Kent School, and The Marvelwood School in Kent
- Forman School in Litchfield
- The Taft School in Watertown
- The Hotchkiss School and Salisbury School farther up in the northwest corner
That's a lot of families coming through a small corner of the state, many from far away. They usually want more out of the trip than the campus and a hotel.
The visits that bring parents here
Move-in and the start of the year
Late summer move-in is usually the warmest school visit of the year, and the lake is still in full summer mode. After the dorm room is set up, an afternoon of swimming and tubing is a good last family outing before the school year starts. It works especially well for new students who are nervous about the first night.
Family weekend in the fall
Most boarding schools hold a fall family or parents' weekend. Early fall is one of the best times on the lake: the water is quiet, the summer crowds are gone, and the hillsides around Lillinonah start turning. A fall foliage cruise is a calm, scenic way to spend a couple of hours with your student between games and conferences. If you're deciding how to see the leaves, read fall foliage boat cruise vs. hiking.
Fall family weekends line up with some of the best scenery on the lake.
Spring visits and graduation
By late spring the lake is open again. Graduation weekends bring grandparents, siblings, and sometimes a few classmates' families. A private pontoon charter or group event is an easy way to celebrate together without booking a banquet room. Seniors who have spent four years near the lake often want one last day on it.
Admissions tours and revisit days
Families touring schools often see two or three campuses in a weekend. A few hours on the water between tours is a good break, and it shows a prospective student what weekends here can look like.
Some of the best charters we run are parents' weekend trips where a student brings their roommate along. The parents get to meet the friends they've been hearing about, and the kids get an afternoon off campus. Everybody wins.
Bring your student's friends
Boarding students don't get off campus often, and a parent visit is their chance. Our pontoons carry a group, so you can bring your student's roommate or teammates for tubing, a swim stop, or a watersports charter with wakeboarding and waterskiing. Students without much water experience can start with tubing. The ones who already ski can push it further with our coaches. Always check your school's sign-out policy before taking other students off campus.
Spending more time here? Think long term
Some school families find themselves in the Litchfield Hills so often that they start to put down roots. They rent a lake house for the summer, keep a weekend place near campus, or buy a home on the water. If that's where you're headed, a weekly charter gets expensive. A long-term rental gives you your own boat for the month or the season.
Our long-term rental site, Conn Boat Rentals, offers weekly and full-season rentals on pontoons, ski/wake boats, and bowriders, delivered to your dock on Candlewood Lake, Lake Waramaug, Highland Lake, Woodridge Lake, and other lakes on request. If you're weighing a lake house, see our guide to buying a lake house in Connecticut and our lake life real estate page. For the boat side, read renting vs. owning a boat in Connecticut.
Spending the summer in the Litchfield Hills? See weekly and seasonal boat rentals at Conn Boat Rentals and have a boat delivered to your lake.
Planning a lake day around a school visit
| Visit | What we'd book | Timing tip |
|---|---|---|
| Move-in day | 2-hr pontoon with swim stop + tubing | After the room is set up, before dinner |
| Fall family weekend | Fall foliage cruise | Book as soon as the school posts the date |
| Admissions tour weekend | 2-hr pontoon between campuses | Midday, between tours |
| Graduation | Private pontoon or group event | The morning after, before the drive home |
| Summer near campus | Seasonal rental | Reserve in spring; the fleet is limited |
- Check the school calendar first. Family weekends are packed with games and events. Find the open window, then book around it.
- Book early. Many schools in the region hold family weekend and graduation on similar dates, and our boats fill quickly.
- Dress for the season. Fall mornings on the water are cool even when afternoons are warm. Bring layers. Our lake-day packing list covers the rest.
- Know the sign-out rules. If you're bringing other students, make sure they're signed out with the school.
Quick FAQ
Make your next school visit a lake day
Move-in, family weekend, or graduation, a few hours on Lake Lillinonah with a captain turns a campus visit into a family day your student will remember. Spending the summer nearby? Ask about seasonal rentals.
Book a Charter Seasonal Rentals