New Page
New Page
Watersports Lessons on Candlewood Lake
Lakeside Watersports is closed for the 2026 season. This page stays up as a Candlewood Lake watersports resource — what we taught, where to get on the water now, and who to call when the lake makes you want to stay.
Connor Kostyra · Licensed CT Real Estate Salesperson
RE/MAX Rise · Lic. #RES.0836348
Closed for 2026 — book with Connecticut Water Sports
Lakeside Watersports is closed for the 2026 season. For lessons and active charters — wakeboarding, wakesurfing, tubing, pontoon charters, fishing charters, kids clinics, and group lake events — we recommend Connecticut Water Sports on nearby Lake Lillinonah in New Milford, about 10–15 minutes from Candlewood Lake. Expert captains, top-tier boats, and one of the most-reviewed watersports operations in the state.
Candlewood Lake watersports we were known for
For years, Lakeside Watersports ran lessons and charters out of Candlewood Lake. These were the experiences our guests came back for — preserved here as a record of what the lake has to offer.
Wakeboarding, Wakesurfing & Waterskiing
Our signature lessons. We coached first-timers up on a wakeboard, dialed in the wave for wakesurfers, and taught classic waterskiing behind a proper wake boat — all on the flat morning water of Candlewood Lake.
Tubing & Boat Charters
Family tubing runs and private boat charters were a Lakeside staple. We ran easygoing tube sessions for all ages and captained charter days so guests could relax and enjoy the lake without ever touching the wheel.
Slalom Skiing, Wakeskating & Kneeboarding
For guests chasing the next progression, we offered slalom skiing, wakeskating, and kneeboarding. Whether dropping a ski or learning to ride a wakeskate, these sessions were built around the rider's goals.
These watersports lessons and charters are no longer offered by Lakeside Watersports. They are now available through Connecticut Water Sports on Lake Lillinonah.
Thinking about a place on the water?
Connor Kostyra founded Lakeside Watersports and is now a licensed Connecticut real estate salesperson with RE/MAX Rise. If lake life has you thinking about a place of your own, Connor helps buyers and sellers with waterfront, lake-area, and general Connecticut real estate — Candlewood Lake, Lake Lillinonah, and across CT — and he knows the lake from the water up.
More from Connor: Connecticut real estate with Connor Kostyra · Connor's lake-life real estate page on Connecticut Water Sports.