St. Louis, Missouri
The Gateway Arch, the Mississippi, and frozen custard thicker than your wiring.
St. Louis is where the Midwest starts to feel like the West. You cross the Mississippi on the old Chain of Rocks Bridge, pass beneath the Gateway Arch, and find a city that wears its Route 66 history lightly but proudly. Short riding day in, big evening out.
“We crossed the Mississippi on the Chain of Rocks approach and stopped arguing about who'd seen the Arch first. The concrete at Ted Drewes is thicker than your wiring — order it, hold it upside down, take the photo.”
History
St. Louis was the jumping-off point for every westward push in American history — Lewis and Clark, the steamboats, the wagon trains and finally Route 66. The 630-ft Gateway Arch, finished in 1965, marks the spot. Route 66 crossed the Mississippi here on the Chain of Rocks Bridge, famous for its 30-degree kink in the middle.
Why Visit
The Arch alone is worth the stop, but the city's riverfront, free zoo and frozen-custard culture make it one of the most rewarding overnights on the route. You'll also cross the Mississippi — a real milestone moment.
Best Motorcycle Roads
Chain of Rocks Bridge approach
Ride the old alignment to the bridge — now a cycling/walking landmark you can't ride across, but the approach is atmospheric.
Riverfront Trail
The levee roads along the Mississippi give you skyline views and the mighty river beside you.
Best Hotels
Drury Plaza St. Louis
Mid-rangeA restored historic bank building on the riverfront, a short ride from the Arch. Secure parking and free breakfast.
Hotel Mayflower (boutique)
PremiumA 1925 landmark reborn in the Central West End — proper character and a great bar for the evening.
Best Restaurants
Ted Drewes Frozen Custard
Frozen custard
The St. Louis Route 66 institution. Order a 'concrete' — it's so thick they hand it to you upside down. Do not skip.
Must Try · The Concrete (any flavour)
Pappy's Smokehouse
BBQ
Memphis-style smoked ribs and pulled pork — arrive early, they run out.
Hidden Gems
- The Chain of Rocks Bridge at dusk — you can walk it and watch the river change colour.
- The City Museum — part playground, part sculpture, entirely bizarre. Worth a spare hour.
- The Hill neighbourhood for genuine Italian-American restaurants off the tourist trail.
Photography Spots
- The Gateway Arch from the riverfront steps, framed against the sky.
- Your bike beside the old Route 66 shield painted on the road near the bridge.
- Ted Drewes' neon sign at night.
Sunrise & Sunset
Around 6am. The Arch catches first light beautifully from the east side of the river.
Behind the Arch from the riverfront levee — classic St. Louis shot.
Practical Information
- QuikTrip on Hampton Avenue — multiple pumps, easy bike access.
- Phillips 66 near the I-44/66 junction, handy as you head west.
Downtown metered parking is cheap and plentiful. Many garages won't take bikes — use street meters and the riverfront lot. The Arch grounds have free bike parking.
Suggested Walking Routes
Arch Grounds to Riverfront
A flat 1.5-mile loop through the Arch park and down to the Mississippi — the best way to feel the city.
Central West End stroll
A 40-minute wander through tree-lined streets and bistros near the Mayflower.
Weather & Ride Difficulty
Hot, humid summers (32°C with sticky air), mild pleasant springs and autumns. Thunderstorms build fast in summer afternoons — check the radar before you leave. Winter can be icy.
Urban approach needs care, but the riding day itself is short and easy. Watch for sudden summer storms.
Nearby Attractions
- Gateway Arch National Park
- Chain of Rocks Bridge (walkable)
- City Museum
- Forest Park (free zoo and museums)
Frequently Asked Questions
No — it's a walking and cycling bridge now. But you can ride to the approach and walk it for the views and the photos.
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