Captained wakeboarding, waterskiing, wakesurfing, and tubing charters — the closest professional operation to Candlewood, just 10 minutes north on Lake Lillinonah.
If you're searching for watersports on Candlewood Lake, here's the straight answer: there isn't a captained watersports charter operating on Candlewood itself. The good news is we're right up the road. Connecticut Water Sports runs captained watersports charters on Lake Lillinonah in New Milford — about a 10-minute drive north of Candlewood Lake.
For guests in New Fairfield, Brookfield, Sherman, Danbury, and the surrounding Candlewood area, we're the closest professional watersports charter you'll find — a quick drive north for a proper lakeside watersports day on Lake Lillinonah. Show up, step on the boat, and the captain handles the rest.
Our launch is at 143 West St, New Milford, CT — a straightforward drive up Route 7 from the Candlewood Lake area. View on Google Maps.
Lake Lillinonah stretches roughly 14 miles up the Housatonic River with quiet coves and open water for wakeboarding, skiing, and tubing.
Plenty of room for a family day, a friends' afternoon, or a small group celebration on our dedicated watersports boat.
Morning glass for early skiers, midday tubing, or an evening wakesurf session — we run all day, every day in season.
Our watersports charters cover the full spread. You can mix and match across the boat — or just pick one thing and spend the whole session on it.
Beginner-friendly coaching or just driving for experienced riders. Our captains dial in the wake, the speed, and the rope so you get the runs you want.
Single ski, double skis, slalom — whatever you ride, we've got the gear and a pro driver who knows how to pull a clean set.
The crowd-pleaser. Big tubes, gentle spins for the kids, or faster runs for the brave. Always a hit with families and groups.
Not everyone has to ski. Up to 10 guests can pile on, swim, watch, or just enjoy the lake. The boat is yours for the hour.
Plenty of sites talk about Candlewood Lake. We’re the ones actually running captained watersports charters for the families and groups who live on and around it. Connecticut’s only watersports school, professional captains on every trip, all gear and fuel included — no rental boats, no bareboat waivers, no contact-form runaround. You book online, show up at our New Milford launch, and step on the boat.
Real families from New Fairfield, Brookfield, Sherman, and Danbury who’ve been out with us — not a social-media follower count.
A pro driver on every trip. No boating license or experience needed — we teach complete beginners every day.
A quick drive up Route 7 to 143 West St, New Milford. Free parking, on the water in minutes.
Coming up from Candlewood for something specific? We run dedicated charters and lessons for each:
Booked by the hour. Gratuity not included.
Check AvailabilityIf watersports aren't your speed, we also run captained pontoon charters on the same lake at $275/hour — lake tours, sunset cruises, and swim stops for up to 12 guests. See our pontoon charters page for details, or call us if you want to talk through what makes sense for your group.
Real reviews — 5.0★ across 300+ on Google and 5.0★ across 79 on TripAdvisor.
“This is our 4th annual outing with CT Water Sports and it was amazing!” — Captains Phil and Henry helped kids ages 7 and 9 feel safe while wakeboarding.
Melissa C.
“It was our fourth time with Connecticut Watersports this summer. Captain Phil did an incredible job” — waterskiing, wakeboarding, and tubing for both experienced and first-time riders.
Vince D.
“This is my third time having Ian and his wonderful team treat my 4 grandkids… the one thing they request to do every year.”
Kris T.
If you're around Candlewood and want your family on the water this season, here's how the options actually shake out in 2026:
Owning a boat on Candlewood means a slip or a lift, winterization, insurance, maintenance, and the busiest weekend boat traffic in Connecticut. Great if you're on the lake full-time; a lot of overhead for a handful of weekends.
Bareboat rentals put you behind the wheel — which means a licensed operator in your group, liability on you, and nobody to teach the kids to get up on skis. And on summer Saturdays, Candlewood's open water gets choppy by 10am from sheer traffic.
A captained charter flips all of that: a pro driver who grew up pulling skiers, all the gear on board, insurance and safety handled, and coaching included. You book a time slot online, drive 10 minutes up Route 7, and you're riding. That's what we do — and we're the only watersports school in Connecticut doing it.
When to come: our season runs Memorial Day through October. Early mornings are the secret — Lillinonah at 8am is glass, which is when the serious skiers and wakesurfers book. Midday is tubing-and-swimming time; evenings are wakesurf sessions and golden-hour cruises. October is foliage season on the Housatonic and the lake is nearly empty.
Your first charter: park free at West Cove Marina, meet your captain at the dock, life vests and gear are already on the boat. Total beginners usually get up on a wakeboard or skis within the first hour — our captains teach this every single day.
Straight up Route 39 to Route 7 — about 15 minutes to our dock. Our biggest source of Candlewood-area families and summer birthday charters.
Route 7 north, roughly 10 minutes. Brookfield groups love the after-work evening wakesurf slots — on the water by 5, home by dark.
Down Route 39 along the lake, about 15 minutes. Sherman kids are regulars at our weekly waterski and wakeboard clinics.
Route 7 north, about 20 minutes. Corporate groups and big-family days — pair the watersports boat and pontoon for parties over 10.
Since we're about 10 minutes away on Lake Lillinonah, we aren't able to offer lakeside pickups on Candlewood. Guests meet us at our New Milford launch on Lake Lillinonah — an easy drive up Route 7 — and we handle everything from there.
Yes. Every charter is captained by a pro driver who teaches complete beginners every day — first-time wakeboarders, kids on skis, adults who've never been behind a boat. If you can swim, we can teach you. No boating license or experience needed.
Captain, fuel, and all equipment are included — wakeboards, waterskis, wakesurf boards, and tubes, plus life vests. Up to 10 guests. Bring suits, towels, sunscreen, and any food or drinks you want (BYOB is welcome). Gratuity is not included.
Charters are booked by the hour — most groups do 2–3 hours. Book online through our FareHarbor reservation page, or call or text (860) 295-4640 and we’ll help you pick the right trip. We’re open daily 8am–7pm in season.
Questions about coming up from Candlewood? Call or text (860) 295-4640, or check our main site for the full lineup.