Lakeside Watersports offers luxury wakeboarding, water skiing, wakesurfing, and tubing on Candlewood Lake, CT.
Near Westchester, NY, we provide expert lessons, premium equipment, and a safe, unforgettable experience for all ages. Lakeside Watersports offers a luxury experience in wakeboarding, water skiing, wakesurfing, and tubing on beautiful Candlewood Lake in Western Connecticut, just a short drive from New York. We provide personalized or group lessons for all skill levels, and all ages are welcome. Book now for an unforgettable summer adventure on the water!
01/21/2026
2016… I looked and said over his shoulder “a time where we literally were able to die, and just keep doing it again.”
That was the year of owning the G23 which in my head was you don’t have any excuses to not be the best.
05/27/2025
Our Wave 🌊 is immaculate and so is the instruction & vibes 💎 on
We have wetsuits still if needed!
Lakeside Watersports creates lasting summer memories by providing private watersports lessons & boat charters on picturesque Candlewood Lake.
03/01/2025
Book Now, Decide Later – Summer Made Easy! 😎 -
✅ Decide later – Our 5-day reschedule/refund policy means you have the flexibility to adjust your plans as the date gets closer.
02/26/2025
🚤 Now’s the Time to Plan Your Summer Adventures! ☀️
Looking for fun, easy summer activities in the NY/CT area? Lakeside Watersports on Candlewood Lake is the perfect stress-free day trip—just show up, and we take care of everything!
✔️ No planning, no hassle—just bring a swimsuit & towel
✔️ Wakeboarding, wakesurfing, tubing & more
✔️ Conveniently located for NYC, Greenwich & Westchester
Make a full day out of it with lunch at Down The Hatch and ice cream at Ferris Acres Creamery! 🍦
📅 Summer 2025 bookings are already filling up—don’t wait!
We know that in 2025, tip fatigue is real—so we’re making things easier for you. At Lakeside Watersports, what you pay for your session is all you need to pay.
02/08/2025
Secure ✅ Your Spot on Our Boats for Summer 2025 -
Looking for the perfect way to celebrate a corporate event, birthday party, or special gathering on the water? Now is the time to book with Lakeside Watersports—Connecticut’s #1 Watersports Company!
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Started by two local guys who decided to share their passion for watersports with New England, Lakeside is based on two very important principles: Safety and Affordability.
It is our mission to provide every customer with fun-filled summer memories. Come take a ride behind our boat and experience what it feels like to glide across the water with nothing but a smile on your face!
Lakeside Priorities
SAFETY
Safety is our number one priority. Boating and watersports require quite a bit of preparation and responsibility. It is our goal to not only provide you with the best possible experience on the water, but also ensure the safety of everyone on board. All customers will receive proper instructions and top notch, Coast-Guard approved safety equipment. Rest easy know that your instructors have 1,000s of hours of boating and teaching experience combined with lifeguard and EMT training.
AFFORDABILITY
Our other main focus is promoting affordable watersports. We understand that enjoying the water can become expensive very quickly. The boat alone can be a huge expense, which does not even include the cost of gas and equipment. These prices will scare just about anyone away from the watersports lifestyle. Here at Lakeside Watersports, we intend to provide all kinds of summer fun, without having to break the bank.