Introduction
There’s a reason Route 66 has always been described as a road that goes somewhere — and that somewhere, for the eastern half of America, is St. Louis. Perched on the western bank of the Mississippi River, St. Louis is where the Mother Road begins (or ends, depending on which direction you’re traveling). Cross the river from Illinois and you’re stepping onto one of the most storied stretches of asphalt in American history.
St. Louis isn’t just a waypoint on Route 66 — it’s a destination in its own right. The Gateway Arch dominates the skyline, the blues drift out of bars in Soulard, and neighborhoods like Maplewood and Lindenwood Park have preserved the neon and brick of the old highway era better than almost anywhere else along the route. Whether you’re a first-time Route 66 traveler or a seasoned road tripper chasing every alignment, St. Louis rewards the curious.
With the 2026 Route 66 Centennial approaching, there’s no better time to start your journey — or end it — right here on the banks of the Mississippi.
A Brief History of St. Louis
St. Louis was founded in 1764 by French fur traders Pierre Laclède and Auguste Chouteau, who recognized the strategic value of the site — just south of the confluence of the Missouri and Mississippi rivers. It changed hands from France to Spain and back before the United States acquired it as part of the Louisiana Purchase in 1803. Lewis and Clark launched their famous Corps of Discovery expedition from just across the river, cementing St. Louis’s identity as the literal gateway to the American West.
The city grew into a major industrial and transportation hub through the 19th century. The completion of the Eads Bridge in 1874 — the first steel truss bridge across the Mississippi — connected St. Louis to the east and accelerated commerce. By the time Route 66 was commissioned in 1926, St. Louis was one of the largest cities in America, a natural anchor for any coast-to-coast highway.
The 1904 World’s Fair (officially the Louisiana Purchase Exposition) put St. Louis on the global map and gave the city lasting culinary legends — the ice cream cone and the hot dog bun are both said to have been popularized there. That civic ambition never quite faded. The Gateway Arch, completed in 1965, was built as a monument to westward expansion and remains one of the most recognizable structures in America.
For Route 66 travelers, the most relevant part of St. Louis history is its role as a manufacturing and distribution center through the mid-20th century — the era when the highway was in its prime. The Route 66 corridor through the city passed through working-class neighborhoods full of filling stations, motor courts, diners, and taverns that served the steady stream of travelers heading west.
Route 66 History in St. Louis
When Route 66 was officially commissioned on November 11, 1926, St. Louis was designated as one of its major terminal cities. The original eastern terminus was actually in Chicago, but St. Louis functioned as the practical gateway to the West — the last major metropolitan area travelers would pass through before the plains and deserts of the interior.
The original alignment through St. Louis followed a complex path through the urban core, crossing the Mississippi via the McKinley Bridge into Venice, Illinois, or later via the Municipal (MacArthur) Bridge. The route wound through downtown and then southwest through city neighborhoods before heading toward the suburbs. This urban routing created one of the most layered and historically complex sections of the entire highway.
Route 66 was realigned multiple times in the St. Louis area. A significant shift in 1936 moved traffic to the Chain of Rocks Bridge (now a beloved pedestrian and cycling landmark) north of the city. The 1955 bypass pushed traffic further around the urban core as part of early freeway planning. By the time Interstate 44 was completed through the area in the 1960s and 70s, the old Route 66 corridors were left behind — some to decay, others to quietly survive.
Preservation efforts have been active in St. Louis since the 1990s. The Route 66 Association of Missouri, local neighborhood organizations, and city planners have worked to identify, restore, and mark historic alignments. Today, several sections of the original roadway are well-signed and drivable, and the city has embraced its Route 66 heritage as both a tourism asset and a point of civic pride.
Historic Route 66 Alignments in St. Louis
Driving the historic alignments through St. Louis requires a bit of planning, but the effort is worth it. Here are the key segments to know:
The Chain of Rocks Bridge (1936–1977 alignment)
The Chain of Rocks Bridge carried Route 66 traffic across the Mississippi from 1936 until the interstate era. Its most distinctive feature is a 22-degree bend midway across — built to avoid a water intake structure below. The bridge is now closed to vehicles but open to pedestrians and cyclists, and it offers one of the best views of the St. Louis skyline available. Park on the Illinois side (off I-270) and walk across. It’s free and unmissable.
Gravois Avenue and Watson Road
Southwest of downtown, Route 66 followed Gravois Avenue and then Watson Road through the city and into the suburbs. This corridor — particularly through Maplewood and Crestwood — still retains significant Route 66 character, with vintage commercial buildings, old signage, and businesses that have been operating since the highway era. Watson Road in particular is a rewarding slow drive.
Bypass 66 / Chippewa Street
An earlier alignment ran along Chippewa Street through the South City neighborhoods, passing through working-class residential and commercial areas that retain much of their mid-century fabric. The Ted Drewes Frozen Custard stand on Chippewa Street is the most famous surviving Route 66 landmark along this alignment — and one of the most beloved in the entire city.
Route 66 Attractions in St. Louis
St. Louis offers more genuine Route 66 history than almost any other city on the route. Here are the essential stops:
1. Ted Drewes Frozen Custard
6726 Chippewa Street, St. Louis, MO 63109
If there is one stop in St. Louis that every Route 66 traveler must make, it’s Ted Drewes. Open since 1931, this frozen custard stand on the historic Chippewa alignment is a true survivor — still family-owned, still serving the same recipe, and still drawing lines out the door on summer nights. Order a concrete (a custard so thick it’s served upside down) and join the crowd of locals and travelers. Seasonal operation — open late spring through early winter.
2. Gateway Arch National Park
11 N. 4th Street, St. Louis, MO 63102
Not a Route 66 landmark per se, but you cannot come to St. Louis and skip the Arch. The tram ride to the top offers a unique perspective on the city and the Mississippi — and on a clear day you can see for miles in either direction. The museum beneath the Arch covers westward expansion in depth. Budget at least two to three hours.
3. Chain of Rocks Bridge
10950 Riverview Drive, St. Louis, MO 63137 (Missouri access)
The iconic bent bridge that carried Route 66 traffic across the Mississippi from 1936 to 1970. Now a pedestrian and cycling landmark, it’s one of the most photographed spots on the entire route. The walk across is about a mile each way, with the St. Louis skyline framing one end and the Illinois floodplain on the other.
4. Mural of Route 66 (Maplewood)
Manchester Road at Greenwood Avenue, Maplewood, MO 63143
The suburb of Maplewood, just west of the St. Louis city limits, has leaned hard into its Route 66 heritage. A large mural depicting Route 66 history anchors the downtown, and the surrounding blocks on Manchester Road have several vintage commercial buildings. Maplewood hosts Route 66 events and markets itself as a Route 66 destination.
5. St. Louis Car Museum & Sales
1575 Woodson Road, Overland, MO 63114
A collection of vintage and classic American automobiles — many of them the very cars that would have traveled Route 66 in its heyday. For car enthusiasts, this is a natural stop in the St. Louis area.
6. Coral Court Motel (Historic Site)
Watson Road near Marlborough, St. Louis County (site only; motel demolished 1995)
The Coral Court was one of the most architecturally distinctive motor courts on all of Route 66 — a streamline moderne complex with tan glazed tile and individual garages for each unit. Demolished despite preservation efforts in 1995, it lives on in photographs, documentaries, and the imaginations of Route 66 enthusiasts. A reconstructed unit is on display at the Missouri History Museum. The site itself is worth a brief stop for serious Route 66 travelers.
7. Missouri History Museum
Lindell Blvd at DeBaliviere Avenue, Forest Park, St. Louis, MO 63112
Admission is free. The museum holds significant Route 66 collections including artifacts from the Coral Court Motel, vintage signage, and exhibits on Missouri transportation history. Worth a visit even for travelers on a tight schedule — the Route 66 material alone justifies the stop.
8. Soulard Neighborhood & Anheuser-Busch Brewery
1200 Lynch Street, St. Louis, MO 63118
While not on the Route 66 alignment itself, the Anheuser-Busch brewery complex is one of the great industrial landmarks of St. Louis — and beer was very much part of the Route 66 roadside economy. Free tours are available. The Soulard neighborhood surrounding it is one of the city’s oldest and most atmospheric, with 19th-century brick townhouses and a famous farmers market.
9. St. Louis Walk of Fame (Delmar Loop)
6504 Delmar Blvd, University City, MO 63130
The Delmar Loop is one of the most vibrant commercial districts in the St. Louis area — independent shops, restaurants, and a classic movie theater. The Walk of Fame honors famous St. Louisans with bronze stars embedded in the sidewalk. A good spot for an evening stop, a meal, or a browse.
10. Purina Farms (Gray Summit, MO — nearby)
200 Checkerboard Drive, Gray Summit, MO 63039 (approx. 35 miles southwest on Route 66)
Just down the road on Watson Road / Route 66, Purina Farms is a free family-friendly attraction with animal shows, a petting zoo, and agricultural exhibits. A good stop if you’re traveling with children and heading southwest out of St. Louis.
Where to Stay in St. Louis
St. Louis has a full range of accommodation, from major downtown hotels to smaller properties along the Route 66 corridor. Here are the most relevant options for Route 66 travelers:
The Moonrise Hotel — University City
6177 Delmar Blvd, University City, MO 63130 | [BOOKING AFFILIATE LINK]
A boutique hotel on the Delmar Loop with a strong mid-century design aesthetic — think Space Age meets Route 66 nostalgia. The rooftop bar has good views and is a popular spot with locals. Walking distance to restaurants, shops, and the Walk of Fame.
Drury Plaza Hotel at the Arch
2 S. 4th Street, St. Louis, MO 63102 | [BOOKING AFFILIATE LINK]
A reliable mid-range hotel in a converted historic building right in downtown, steps from the Gateway Arch and the riverfront. Drury properties are known for their value-added amenities (hot breakfast, evening drinks) which can help keep costs down on a road trip budget.
Maplewood and Watson Road Corridor — Chain Hotels
If you want to stay on the Route 66 corridor itself, the Watson Road and Manchester Road stretches in Maplewood, Crestwood, and Sunset Hills have several mid-range chain properties (Holiday Inn Express, Courtyard Marriott, etc.) that put you right on the historic alignment. | [BOOKING AFFILIATE LINK]
Where to Eat in St. Louis
St. Louis has a distinctive food culture that Route 66 travelers should make the most of. A few things you won’t find elsewhere:
Ted Drewes Frozen Custard — See Attractions above
Worth repeating. A concrete from Ted Drewes is one of the defining food experiences on Route 66.
Hodak’s Restaurant & Bar
2100 Gravois Avenue, St. Louis, MO 63104
Right on the historic Gravois alignment. Hodak’s has been serving fried chicken and cold beer in South St. Louis since 1940. The dining room is unpretentious, the chicken is crispy, and the portions are generous. A classic St. Louis neighborhood restaurant with Route 66 bones.
Eat-Rite Diner
622 Chouteau Avenue, St. Louis, MO 63103
A tiny, cash-only diner that has been feeding St. Louisans since 1949. Open late — which is when it really shines. Known for its sliders, chili, and no-frills atmosphere. It looks exactly like a diner from the Route 66 era because it is one.
Imo’s Pizza
Multiple locations throughout St. Louis
St. Louis-style pizza is a legitimate regional food tradition — thin cracker crust, Provel cheese (a processed blend of provolone, Swiss, and cheddar), and square-cut pieces. Imo’s is the most iconic chain. It’s not for everyone, but you should try it at least once.
Soulard Market & Neighborhood Restaurants
The Soulard neighborhood, south of downtown, has one of the best concentrations of independent restaurants and bars in the city. The Saturday farmers market is one of the oldest public markets in the country. Good options for breakfast, lunch, or a pre-road-trip dinner.
Tips for Visiting St. Louis on Route 66
Allow More Time Than You Think
St. Louis is frequently underestimated by Route 66 travelers who plan to blow through in a few hours. The city deserves at least a full day, ideally two. Between the Chain of Rocks Bridge, the Chippewa alignment, the Watson Road corridor, and the downtown riverfront, there’s genuinely a lot to cover.
Drive the Alignments Methodically
Download a dedicated Route 66 navigation app (Historic Route 66 or Maps.me with a Route 66 overlay) before you arrive. The urban routing through St. Louis is complex, and GPS apps that optimize for speed will route you onto I-44, which misses the point entirely. A printed map from the Missouri Route 66 Association is also worth having.
Parking
Downtown St. Louis has ample parking garages near the Gateway Arch (the national park has its own lot). Along Watson Road and Manchester Road in the suburbs, parking is easy at individual businesses. The Chain of Rocks Bridge has a free parking area on both the Missouri and Illinois sides.
Best Time to Visit
Spring (April–May) and fall (September–October) offer the best weather for driving and walking the historic areas. St. Louis summers are hot and humid, which can make outdoor attractions uncomfortable. Ted Drewes is closed in winter, which is reason enough for many Route 66 travelers to plan a warm-weather visit.
Notable Events
The St. Louis Art Fair (June, Clayton), the Maplewood Route 66 Festival (check local listings for dates), and the Greater St. Louis Auto Show (January) are all worth checking if your timing aligns. Forest Park — one of the largest urban parks in the country — hosts free outdoor events throughout the warmer months.
The 2026 Route 66 Centennial
Route 66 turns 100 in 2026, and St. Louis is one of the cities best positioned to celebrate. As the eastern gateway to the highway — the last major American city before the road heads west into the heartland — St. Louis carries particular symbolic weight in the Centennial story.
Booking.com is an official partner of the 2026 Route 66 Centennial, which makes it a natural platform for planning your accommodations along the route. Expect increased programming, events, and national media attention on Route 66 destinations throughout 2026 — St. Louis will be among them.
If you’re planning a full Route 66 road trip, 2026 is the year to do it. Starting or ending in St. Louis puts you at the historic heart of the Centennial. The Missouri Route 66 Association is expected to host commemoration events — check their website for the latest details as 2026 approaches.
Final Thoughts on St. Louis
St. Louis isn’t always given the credit it deserves as a Route 66 city. Travelers sometimes treat it as a logistical waypoint — cross the river, find the highway, keep moving. That’s a mistake.
The city has Route 66 history woven into its streets in a way that feels lived-in rather than museumified. Ted Drewes is still serving custard the same way it did in 1931. The Chain of Rocks Bridge still bends at that impossible angle over the Mississippi. Watson Road still has the bones of a great American highway corridor. And the Gateway Arch — whatever era it belongs to — looks out over a river that made this whole westward migration possible in the first place.
Give St. Louis the time it deserves. You’ll leave with a full stomach, a better understanding of the road, and a strong argument for why this city belongs at the top of any Route 66 itinerary.
