Entry No. 61 — the Chicago file — filed under: after-dark
Wateriders Moonlight Paddle
After dark the Chicago River empties of tour boats and Wateriders sends small groups out in kayaks under the lit-up skyline, gliding past Marina City's corncob towers and the glowing canyon of downtown. The water is calmer and quieter at night, and on Friday and Sunday paddles you drift beneath the giant projected animations of Art on theMART. The outfitter has been running urban kayak trips here since 1997.
The story
By day, the Chicago River is a noisy, churned-up trench for heavy diesel tour barges and water taxis. But around twilight, the commercial boat traffic clears out, the surface settles into a dark mirror, and the canyon between 800-foot skyscrapers turns surprisingly silent. Wateriders—who have been launching human-powered craft off the Kingsbury Street dock behind the East Bank Club since 1997—runs small groups right into that off-hours stillness.
You push off near the confluence where the North Branch meets the main stem, gliding past Bertrand Goldberg’s twin corncob towers at Marina City with city lights doubled in the black water. On Friday and Sunday night outings, the route brings you directly under the 2.5-acre facade of the Merchandise Mart, where you can rest your paddle across the deck and float while giant projected digital artwork ripples across the stone above you.
What it's like
You will check in at the Kingsbury Street launch behind the East Bank Club, where guides fit life vests and conduct a 25-minute land orientation covering stroke basics before you get on the river for roughly 90 minutes. Expect paddle drip to get your shorts or deck wet—dress in quick-drying synthetic clothing and leave denim at home. The trip feels calm and conspiratorial rather than strenuous, with a small fleet of illuminated kayaks moving slowly through the city center. Book ahead, and aim for a Friday or Sunday slot if you want your floating timed with the Art on theMART projections.
The move: Book a Friday moonlight paddle in a tandem kayak and float beneath the projected art on theMART with the skyline doubled in the dark water.
📍 Before you go Seasonal (warm months); offered select evenings (often Fri/Sun/Mon). Basic paddling lesson and life vest included; book ahead.
- 📍 River North / Kingsbury, Chicago
- 💸 $
- ⚡ Low-key
- 🌗 Outdoors
Where: Kingsbury St launch, Chicago, IL (near North Branch Chicago River)
Hours: Added 2026-06-23 — confirm current hours before you go.
⚠ Seasonal or scheduled — always check before you go.
Pair it with
- Bordel — Trade the cool night water of the river for a candlelit velvet cabaret hidden up a set of leopard-print stairs in Wicker Park.
- Dorian's Through the Record Shop — Transition from floating past lit-up skyscrapers to sipping cocktails behind a working vinyl record shop's listening booth.
- Piva Beer Spa — Follow up an evening of paddling by soaking your shoulders in a warm wooden tub filled with hops and dark beer extract.
Good to know
Do I need prior kayaking experience to join?
No. The tour includes a 25-minute ground safety lesson and paddling orientation before launching, and life vests are provided for all participants.
How long does the entire Moonlight Paddle take?
Plan for about two hours total: roughly 25 minutes for ground orientation and gear fitting, followed by approximately 1.5 hours on the water.
Can I choose between a single or double kayak?
Yes. You can select either a single kayak (weight capacity around 275 lbs) or a double tandem kayak (weight capacity around 475 lbs) when you arrive at the dock.
What should I wear for a night paddle on the river?
Wear water-friendly clothes and shoes that can handle paddle splash. Denim is strongly discouraged because it holds water and gets cold after dark.
Plan a visit & invite your people →
Further reading: Official site · Yelp · Tripadvisor · Time Out
last checked: 2026-06-23