Now Hiring in Madison · Trolley Pub & Paddle Pub Careers

Get paid to host the best day
in Madison.

Join the Trolley Pub & Paddle Pub Madison crew — 14-person pedal-powered pub bikes through downtown and 16-passenger party boats on Lake Monona. Flexible shifts, generous tips, paid training, and a team that feels like summer camp for grown-ups.

Join the Madison Crew

We're hiring for both brands. Apply to the role that fits you best — or apply to both. No prior experience required; we train you fully (and pay you to do it).

Trolley Pub Madison

Trolley Pub Driver / Tour Host

📍 Madison, WI 53703 💵 $12.50 – $40.00/hr (base + 100% tips) 🕒 Part-time · Seasonal

Operate our 14-person pedal-powered party bike on two-hour guided pub crawls through downtown Madison. You're driver, entertainer, and tour guide in one — lead safety briefings, manage bar stops, run the mic, and keep the energy up. Clean driving record required; no tour experience needed.

Paid Training 100% Tips Flexible Weekends + Evenings Review Bonuses

Apply on Indeed →

Paddle Pub Madison

Boat Captain — Paddle Pub Madison

📍 Monona, WI 53713 · Lake Monona 💵 $20.00 – $40.00/hr (base + tips) 🕒 Seasonal · May – October

Captain a 16-passenger pedal-powered party boat on Lake Monona — bachelorette parties, corporate events, and sunset cruises. Handle solo docking, run safety briefings, verify waivers, and coordinate with your first mate to deliver the best day on the water. Must be 21+ with Wisconsin Boater Safety Certificate (or willing to get one before start).

Paid Training Tips On the Water Weekends + Holidays 21+

Apply on Indeed →

Madison Hiring & Training Event

April 21–22, 2026 — two days of paid interviews, classroom onboarding, and hands-on training. Open to new applicants and existing staff. All training hours paid at $12.50/hr.

Walk-in Hiring Day

Tuesday, April 21 · Noon – 5:00 PM

Doubletree by Hilton Madison Downtown · Conference Room. Drop in to interview, complete onboarding, and start classroom training the same day.

Get Directions

Tue · 12:00 – 5:00 PM

Hiring & Classroom Training Paid

Doubletree Madison Downtown — Conference Room · Map ↗

Interviews, onboarding paperwork, brand & safety, POS & guest experience.

Wed · 10:00 AM – 1:00 PM

Trolley Pub Ops Training Paid

555 W Washington Ave, Madison · Map ↗

Pre-trip inspection, pedal & brake systems, route, boarding, close-out.

Wed · 2:00 – 4:00 PM

Paddle Pub Ops Training Paid

Breakwater · 6308 Inland Wy, Monona · Map ↗

Dock procedure, captain duties, safety & PFDs, weather calls, service.

Wed · 5:00 PM

Team Dinner Hosted

Breakwater · 6308 Inland Wy, Monona · Map ↗

Casual dinner for all new and existing staff — come meet the crew.

Good Questions

Do I need experience?

For Trolley Pub — no prior experience needed, just a valid driver's license and a clean driving record (no DUIs or suspensions). For Paddle Pub captain — prior boating experience is strongly preferred, and you'll need a Wisconsin Boater Safety Certificate (we can help you get one before your start date). Captains must be 21+.

What's the pay?

Training is paid at $12.50/hr for everyone. Operational shifts are paid hourly plus tips — Trolley Pub drivers earn $12.50–$40/hr with 100% of tips, and Paddle Pub captains earn $20–$40/hr with tips. Google review bonuses available for standout Trolley drivers.

What hours will I work?

Both roles are part-time with flexible scheduling — primarily weekends and evenings, with holidays. Paddle Pub runs May through October. Trolley Pub has a longer season. Tell us your availability and we'll build a shift schedule that works.

Are there any screenings?

Yes — both roles require a criminal background check and drug screening. Trolley drivers also need a clean driving record with no DUIs or suspensions.

Can I work both brands?

Yes — many of our best team members do. It's a great way to pick up more shifts, more tips, and more variety. If you're eligible for both, apply to both.

I can't make the hiring event — can I still apply?

Absolutely. Apply through either link above and we'll reach out to schedule an alternative time.

Get paid to host the best dayin Madison.