Now Hiring — 2027 Season

Hiring 2–3 Great Boat Drivers for Summer 2027

We're looking for experienced boat drivers with proven watersports towing experience — skiing, wakeboarding, wakesurfing, tubing — plus fishing guides who know these waters. $20/hr starting pay plus tips, right here on Lake Lillinonah.

See Open Roles

2027 Season · June through Labor Day

Open Roles for Summer 2027

We're building the 2027 crew now — starting with 2–3 experienced boat drivers. College students home for the summer are welcomed and encouraged to apply.

Guests laughing aboard a CT Water Sports charter boat

Instructor working with kids at a CT Water Sports clinic

Wakesurfer riding behind a CT Water Sports boat

Watersports Guide

2–3 Openings · Towing Experience Required

You run the boat and the show — smooth, safe pulls for skiers, wakeboarders, wakesurfers, and tubers, plus a great guest experience. You'll also drive for our kids watersports clinics: coaching first-timers, safety talks, and cheering kids into their first ski ride. This is a role for drivers who've done it before, not a first-time job.

Proven towing experience · Weekends essential

Fishing Guide

Freshwater Experience

Guide guests to bass, walleye, and trout on the local lakes you already know. Boat and gear provided — you bring the knowledge, the patience, and the catches.

Local lake knowledge · Consistent catcher

Why You'll Love It

Perks That Beat Any Summer Office

Come for the paycheck, stay for the sunsets over Lake Lillinonah.

$20/hr + Tips

Starting pay is $20/hr, and our guests tip well for great days on the water.

Free Boat Time & Gear

Use boats and equipment on off-hours — your own riding and fishing gets better all summer.

Flexible Summer Schedule

Built for college students and teachers — full-time dock-to-dusk or weekend-only shifts both work.

Professional Fleet

Well-maintained boats, quality gear, and an owner who keeps everything ready to run.

Best 'Office' in CT

Your desk is a boat. Your commute is a lake. Your meetings happen at 30 mph with a rooster tail.

What We're Looking For

Simple Requirements

Skills we can teach. Reliability and lake-stoke, you bring.

Proven towing or guiding experience Weekend availability Guest-first attitude College students welcomed $20/hr starting + tips 18+ preferred

Good Questions

2027 Hiring FAQ

The stuff everyone asks before they apply.

Both roles call for real experience. For boat drivers, that's towing skiers, wakeboarders, wakesurfers, or tubers — and being comfortable coaching first-timers, since driving covers our kids watersports clinics too. For guides, it's consistently catching on these waters.

The season runs from early June through Labor Day. Fall foliage charters continue into October for crew who want to stay on.

Absolutely — college students are welcomed. We build schedules around summer dates, and many crew members return year after year.

Starting pay is $20/hr across all roles, plus tips. Drivers and guides working busy weekends build solid tips on top of that.

Fill out the application form below with your name, email, your watersports and boat driving experience, and a little about yourself. We'll be in touch as we start meeting applicants for the 2027 season.

These are seasonal roles (June–Labor Day). Strong performers are always first in line for the following season, and experienced drivers and guides sometimes pick up spring setup and fall foliage charter work.