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Windsor’s riverfront lawn at the foot of Ouellette Avenue, under a giant Canadian flag.
This is the classic start. The Detroit skyline fills the far bank, close enough to read the signs. A short walk east, the Tower of Freedom marks Windsor as a final stop on the Underground Railroad; its partner monument stands across the river in Detroit’s Hart Plaza.
Free public space. Open riverfront park. Bike racks and benches nearby.
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The region’s public art gallery, a block from the river.
A glass-fronted gallery with Canadian historical and contemporary work, and a good place to wait out a shower before the ride west.
Indoor venue: check hours and admission. Check the official site for hours and admission.
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Indoor water park in the downtown aquatic centre. Good for a rest day with kids.
Not a bike stop so much as a reason to stay another night. It sits inside the Windsor International Aquatic and Training Centre, within walking distance of the riverfront.
Indoor venue: check hours and admission. Check the official site for hours and admission.
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The casino and hotel towers on the riverfront, east of the flag.
The towers are a landmark from both banks. The Riverfront Trail runs right past the building, so it is an easy turn-around point for a short evening ride.
Local business: check opening hours. Casino floor is 19+ (Ontario law). Check the official site for events.
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An optional ride east to the old distillery town and its Prohibition stories.
Hiram Walker built his distillery here in the 1850s and a company town grew around it. When the United States went dry in the 1920s, a lot of what crossed the river at night started on this shore.
Indoor venue: check hours and admission. Tours and tastings run on a schedule; check before you ride out.
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Dozens of large outdoor sculptures along the Riverfront Trail, free and open all day.
The trail threads between bronze, steel and stone, with the river on one side and lawns on the other. You ride through it on the way to the bridge, so plan time for photos rather than a detour.
Free public space. Free outdoor park. The trail is shared with walkers.
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A small riverside park right under the Ambassador Bridge, with the best close-up view of it.
The Ambassador Bridge opened in 1929 and still carries a large share of the trade between the two countries. From McKee Park you stand almost underneath it, with Detroit on the far bank.
Free public space. Small public park. Photo stop.
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One of the oldest European settlements in Ontario, now a busy little main street.
Sandwich was laid out in the 1790s, long before Windsor grew up around it. Mackenzie Hall, the old county courthouse, still stands on Sandwich Street, along with brick storefronts and cafés worth a stop before the bridge.
Free public space. Neighbourhood main street. Shops and cafés keep their own hours.
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A star-shaped 1840s fort on the river, the first stop off the bridge on the Detroit side.
Built in the 1840s to guard the river against a British attack that never came, the fort served the U.S. Army from the Civil War to the Vietnam era. The stone walls and barracks are still here, a few minutes from the bridge path exit.
Indoor venue: check hours and admission. Open on set days and for events. Check the official site before you plan around it.
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A tiny old-school coney island diner on West Vernor. Order the coney.
A counter, a griddle and not much else, which is the point. It is a short detour west from Clark Park and an honest lunch before the ride into Mexicantown.
Local business: check opening hours. Check current hours before you go.
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Bakeries, taquerias and murals along Bagley Street and West Vernor.
Southwest Detroit has been the centre of the city’s Mexican community for generations. Ride slowly down Bagley, look up at the murals, and lock up for a pan dulce. Xochimilco, on Bagley, has been a family favourite of the tour’s creator for decades.
Free public space. Neighbourhood. Restaurants and bakeries keep their own hours.
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Detroit’s grand 1913 train station, empty for decades and now restored.
The last train left in 1988 and the station became a symbol of the city’s hard years, and a favourite film set. Ford bought it in 2018 and reopened it in 2024 after a long restoration. This is where the full loop splits: north to the music neighbourhoods, or east to downtown.
Indoor venue: check hours and admission. Public areas open at set times. Check the official site.
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The house on West Grand Boulevard where Berry Gordy built Motown.
From 1959 the Hitsville U.S.A. house was office, studio and family home for the label. The Supremes, Marvin Gaye, Stevie Wonder and the Temptations all recorded in Studio A, which you can still stand in on a tour.
Indoor venue: check hours and admission. Tours are timed and often sell out. Book ahead on the official site, or stop for a photo outside.
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A 1928 Art Deco tower by Albert Kahn, with one of the finest lobbies in the country.
Car money built it: the Fisher brothers made car bodies and wanted Detroit’s most beautiful building. Step inside the arcade and look up at the painted vaulted ceiling.
Indoor venue: check hours and admission. Lobby access and tours vary. Check the official site.
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The home of Detroit techno’s Submerge label, with a small museum inside.
Detroit techno grew out of this city in the 1980s, and Submerge has been one of its homes. Exhibit 3000 inside the building tells that story. Opening is limited, so treat it as a bonus.
Indoor venue: check hours and admission. Opening is limited. Check before you go.
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The brick factory where the first Model T was built in 1908.
Before the giant Highland Park and Rouge plants, Ford made cars on these wooden floors. The building is now a museum full of early cars, and it may be the most Motor City stop on the map.
Indoor venue: check hours and admission. Museum with seasonal hours. Check the official site.
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One of Detroit’s oldest recording studios, in a house on Second Avenue.
An enormous amount of music has been cut in this modest building, from early Motown sessions to Parliament-Funkadelic. It is a working space, not a museum, so enjoy it from the sidewalk unless a public event is announced.
Photo stop from the street. Photo stop from the sidewalk. Public tours only when announced.
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One of the great American art museums, home of Diego Rivera’s Detroit Industry murals.
Rivera painted the murals in 1932 and 1933: twenty-seven panels of the Rouge plant, workers and machines, covering every wall of a courtyard. Even with an hour to spare, go straight to that room.
Indoor venue: check hours and admission. Check the official site for hours and admission.
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An artists’ club behind the DIA, with ceiling beams signed by visiting artists.
Artists who visited the club were asked to sign the lounge beams. Diego Rivera’s name is up there, along with Marcel Duchamp’s and many more.
Indoor venue: check hours and admission. Gallery hours vary. Check the official site.
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Contemporary art in a raw former car dealership on Woodward.
MOCAD keeps the old building rough on purpose, with graffiti walls and big open rooms. Shows change often, so it is different every visit.
Indoor venue: check hours and admission. Check the official site for hours and current shows.
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A 1928 movie palace with a marquee you will see from blocks away.
The Fox opened in 1928 with about 5,000 seats and a lobby built to stun. It was restored in the late 1980s and is still one of the busiest theatres in the country.
Photo stop from the street. See it from the street. Shows and tours are ticketed.
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Eminem’s walk-up spaghetti shop, next to the Fox.
Named for the most famous line in “Lose Yourself”. A quick, fun refuel before the ride down Woodward.
Local business: check opening hours. Check current hours before you go.
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Home of the Detroit Tigers, with giant tiger statues at the gates.
Ride past on a game day and the whole block hums. On other days the tiger statues outside the gates make a good photo.
Photo stop from the street. Photo stop. Games and tours are ticketed.
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Home of the Detroit Lions, built into an old Hudson’s warehouse.
The stadium wraps around a converted brick warehouse, so one whole side looks like an old Detroit building. The blue and silver of this site is a nod to the team across the street.
Photo stop from the street. Photo stop. Games and tours are ticketed.
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The riverfront plaza with the Dodge Fountain, the Underground Railroad memorial and a view back to Windsor.
Movement, Detroit’s electronic music festival, fills the plaza every Memorial Day weekend. At the river’s edge, the Gateway to Freedom memorial looks across to its partner, the Tower of Freedom in Windsor: two monuments to the people who crossed this river to freedom.
Free public space. Public plaza. Closed to through traffic during festivals.
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The glass towers on Detroit’s skyline, where the RiverWalk heads east.
The RenCen is the building you have been looking at from Windsor all day. Behind it, the Detroit RiverWalk runs east along the water and is one of the nicest rides in the city.
Free public space. Public riverwalk. Shared with walkers; ride slowly.
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A sports bar in one of downtown’s oldest buildings, with a Prohibition past.
Ask about the basement. Speakeasy stories come with a lot of Detroit buildings, and this one has more history behind it than most.
Local business: check opening hours. Check current hours. Bar areas may be 21+.
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This route crosses the border. Bring the documents you need to enter each country; requirements depend on your citizenship and status. Border processing time is not included above.
Entering the United States · Entering Canada · CBSA border checklist · Bridge closures
Routes follow OpenStreetMap bike data along Ty’s ride notes. Some legs use streets with traffic. Follow posted signs and local laws, and check conditions before you leave.
Google Maps uses its own bike routing, which may differ from ours.
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