Every summer, thousands of families drive into Litchfield County and the Candlewood Lake area with a car full of duffel bags, sleeping bags, and a kid who is equal parts excited and nervous. Northwest Connecticut is one of the densest summer-camp regions in the Northeast. That means every June, July, and August the same question comes up: we drove all this way, so what do we do with the rest of the day? A lot of those families end up on the water with us. Here's why, and how to plan it.

The short answer

Camp drop-off and pick-up days usually leave a family with half a day to fill near the lake. A captained pontoon or watersports charter on Lake Lillinonah or Candlewood fills it well. Before camp, it's a send-off kids remember. After camp, it's a reunion that isn't spent in a car. You don't need a boat or a license, and you don't need to plan much.

Why northwest Connecticut is camp country

The Litchfield Hills have lakes, woods, and small towns, all within about two hours of New York City and Boston. That's the same mix that brought summer camps here more than a century ago, and it's why so many are still here. Overnight camps, day camps, sports camps, and arts programs are spread across New Milford, Washington, Kent, Litchfield, Morris, Sharon, Salisbury, and the towns around Candlewood Lake.

For families, that means a lot of driving. Many camp families come from Manhattan, Westchester, Long Island, New Jersey, or farther. Opening day and closing day often fall on a weekend, and the drive home is long. Most families we talk to want one good day here, not just a parking lot and a goodbye.

Before camp: the send-off day

Drop-off is usually a tight window. You check in, carry the trunk, meet the counselor, and then you're back in the car. But a lot of families arrive the day before, or have the morning free before an afternoon check-in. That's the window we fill.

  • It burns off the nerves. First-time campers are often anxious the night before. A morning of tubing gets the energy out and gives them a win before they walk into a cabin full of strangers.
  • It's a family moment. Siblings who aren't going to camp get a day too, and parents get time with their camper before they're gone for weeks.
  • It's a head start on the lake. Plenty of camps here have waterfront programs. A kid who has already been behind a boat, or tried a first waterski pull, shows up confident instead of hanging back on the dock.
Kids laughing on a tube behind a boat on a Connecticut lake

A morning of tubing before check-in is the best cure for first-night jitters.

After camp: the reunion day

Pick-up day is different. Your camper has been away for two, four, or seven weeks. They're tanned, a little taller, and they have stories they want to tell now, not in three hours of traffic. A few hours on the boat before the drive home is a much better reunion than the car.

  • Let them show off. Kids who learned to ski or wakeboard at camp want you to see it. A watersports charter gives them the chance, with a captain who sets the pull to their level.
  • Bring their camp friends. Pick-up days are full of families who've become friends over the summer. Our pontoons hold a group, so two or three families can share a charter and one last swim.
  • Slow down before the drive. A swim stop and a sandwich on the lake, then hit the road after traffic has thinned.
From a captain

Our favorite pick-up-day charters are the ones where the kid takes over. They've spent a month learning to get up on skis, and now they want their parents in the boat watching. Most of the time all we have to do is drive.

Visiting weekend and mid-session visits

Many overnight camps hold a visiting day or let families take campers out for an afternoon mid-session. Those hours go fast, and nobody wants to spend them sitting in a restaurant. A two- or three-hour pontoon charter is a good fit: the time is already planned, the kids are outdoors, and you get them back to camp on schedule. Book early. Visiting weekends at several camps tend to land on the same dates, and our boats fill up.

In between: the gap weeks

Camp sessions don't always line up with the rest of summer. Many families have a week or two between sessions, between camp and a family trip, or between camp and the start of school. If you have a lake house, a rental, or relatives nearby, those gap weeks are when the lake gets the most use. Our kids waterski and wakeboard clinics are a good way to keep a camper on the water and building skills between sessions.

Staying for the whole summer? Get your own boat

Some families don't go home between drop-off and pick-up. They rent a lake house for the season so they're close to camp, or they spend the summer in the Litchfield Hills anyway. If that's you, booking a charter every week adds up fast. A long-term rental lets you keep a boat for the month or the season.

Our long-term rental site, Conn Boat Rentals, handles exactly this. They offer 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. Insurance, registration, maintenance, and watersports gear are included. It's the easiest way to have your own boat on the lake without owning one. If you're still deciding, read our breakdown of renting vs. owning a boat in Connecticut.

Summer-long families

Renting a lake house for camp season? See weekly and seasonal boat rentals at Conn Boat Rentals. Get the boat delivered to your dock and use it all summer.

How to plan a camp-day charter

SituationWhat we'd bookTiming tip
Morning before afternoon drop-off2-hr pontoon + tubingStart by 9 a.m.; leave time to change and drive
Day before drop-offWatersports charter or kids clinicAfternoon works; kids sleep better after
Visiting day2–3 hr pontoon with swim stopBook as soon as camp posts the date
Pick-up dayWatersports charter so they can show offLate morning, then drive after traffic eases
Whole summer nearbySeasonal rentalReserve in spring; the fleet is limited

A few practical notes:

  1. Check your camp's schedule first. Confirm check-in and pick-up windows before you book. Camps are strict about timing.
  2. Pack a change of clothes. Nobody wants to show up to check-in in wet swimsuits. Bring towels and dry clothes for everyone. Our lake-day packing list has the rest.
  3. Bring the whole group. Grandparents and siblings can all come. Our pontoons seat a family comfortably, and a captain handles the boat.
  4. Book early for peak weekends. Opening and closing weekends at camps across the region tend to fall on the same dates in late June, mid-July, and mid-August.

Quick FAQ

We're at 143 West St in New Milford, on Lake Lillinonah. Most camps in the Litchfield Hills and around Candlewood Lake are within about 15 to 45 minutes. Check the drive time from your camp before booking around a check-in window.
No. Every charter comes with a licensed captain, life jackets, and gear. You just show up. See do you need a boating license in Connecticut if you're thinking about driving your own rental later.
Yes. This is common on pick-up and visiting days. Call us at (860) 295-4640 with your group size and we'll match you to the right boat.
For one or two outings, a captained charter is simpler. If you'll be on the water every week, a weekly or seasonal rental from Conn Boat Rentals usually works out better, and you get the boat whenever you want it.
We watch the weather closely and will work with you to reschedule if conditions aren't safe. See our cancellation policy for details.

Make camp day a day on the lake

Whether it's the send-off, visiting day, or the reunion, a few hours on Lake Lillinonah or Candlewood with a captain is a camp-day memory for the whole family. Spending the whole summer nearby? Ask about seasonal rentals.

Book a Charter Seasonal Rentals