The charter that showed thousands of people Candlewood Lake.
For years, a private Lakeside charter meant your own MasterCraft wake boat, your own captain, and your own day on the water. The program is retired for 2026, but everything we learned out there still lives here, and it's why we know this lake's homes better than anyone.
Want days like this, always?
The people who loved these charters most are the ones who ended up living here. That's what we help with now.
Talk Candlewood Real Estate →Or start smaller: rent a summer on the lake →
Everything for your day, already handled.
Show up with your crew and sunscreen, we bring the rest.
A premium wake boat
A clean, well-maintained MasterCraft built for a serious wake and a smooth ride. No junk, no surprises.
Your captain & spotter
An experienced local captain runs the boat and a spotter keeps eyes on every rider, so you can relax.
All the gear
Boards, skis, tubes, ropes, and life jackets in a range of sizes, dialed in for your group before you launch.
The local edge
We know the glassy coves for lessons and the best spots to drop anchor, swim, and catch the sunset on Candlewood Lake.
Built for your kind of day.
Families & friends
A private boat for the people you actually want on it. Tube with the kids, ride with the crew, swim between runs.
First-timers & learners
Want to learn to wakeboard or surf? Your captain and crew coach beginners every week, no experience needed.
Celebrations
Birthdays, bachelor and bachelorette days, reunions, or a golden-hour cruise to end the summer right.
Serious riders
A real wake boat and a captain who knows how to shape it. Dial in your session and log your best sets.
Visitors to the lake
In from New Milford, Brookfield, Sherman, New Fairfield, or Danbury? We'll show you Candlewood the local way.
Just here to relax
No pressure to ride. Cruise the shoreline, anchor in a quiet cove, and soak up the day.
Make the day your own.
Mix and match on the water, your captain sets it all up.
What a Lakeside charter looked like.
The formula never changed: no hassle, no experience required.
Charter questions, answered.
What was included in a private boat charter?
Every charter came with a clean MasterCraft wake boat, a captain and spotter, all the gear for wakeboarding, wakesurfing, waterskiing, and tubing, and a quick rundown before heading out. Guests just brought sunscreen, a towel, and their crew.
How many people could come on a charter?
Charters were always private to one group: families, friends, birthdays, and small celebrations on Candlewood Lake.
Did guests need experience?
None at all. The captain handled the boat and the crew set up first-timers every week, from learning to ride to just cruising and swimming.
Can I still book a charter on Candlewood Lake?
Not with Lakeside for 2026, the charter program is retired. But if the lake has you thinking about staying for good, talk to Connor about Candlewood Lake rentals and real estate.
Lakeside Watersports on Candlewood Lake.
The best way to have this day forever? Live here.
Talk to the local who knows every cove, or dive into the Candlewood Lake Watersports guide.