Detroit History Bike Tours (With Strava Maps)
For years, I’ve told people that the best way to see Detroit is by bike. Though it isn’t as personal as exploring the city on foot, you can cover a ton of ground because the Motor City is flat as a pancake. By getting out of the car, you can experience the city how it was designed to be seen, not how the Big Three Automakers convinced you it should be seen.
Each of the rides below features routes that are easy enough to follow and include Strava maps to ensure you don’t get lost. I’ve also included information about each route and linked full posts about the history of the places you’ll be passing along the journey. Detroit’s landscape hides history at every turn, and you never know what you might encounter while cycling through the city.
Before heading out, make sure that you have a bicycle helmet, front and rear lights if you’re cycling early in the morning or evening, and a proper bicycle lock if you plan to stop for food or drinks.
Let’s get started!
Southwest Greenway To Clark Park Ride
This is one of my favorite routes in the closer portion of Southwest Detroit. It passes numerous landmarks that are known worldwide. The trek starts on the newly opened Southwest Greenway, which will later become part of the Joe Louis Greenway once it’s completed. The greenway includes a graffiti museum, which is a neat place to stop and look around.
After dumping out onto Bagley, you’ll get a great view of Michigan Central Station and continue towards the Bagley Street Pedestrian Bridge. The west side of the bridge has sharp turns, so take this portion slowly. From there, you’ll ride through ‘Southwest Proper,’ a popular eating and shopping district with Mexican fare and stores.
After leaving the entertainment district, you’ll pedal through Hubbard Farms, a historic neighborhood with well-maintained homes and gardens, before landing in Clark Park, one of the finest green spaces in the city and where Jack White played ball growing up. You’ll ride around the park and explore the neighborhoods that make Southwest Detroit special along the way.
You’ll go right by Duly’s Place, the best coney island in Detroit, and cycle past Most Holy Redeemer, a catholic parish often credited as the largest in the country after World War II. From there, you’ll continue through the neighborhood, back through Clark Park, across the Bagley Street Pedestrian Bridge, and head back down the Southwest Greenway to where you started.
Palmer Park To Boston Edison Ride
This is one of the simplest rides I’ve planned, but you see a ton of historical aspects of Detroit and Highland Park. Additionally, you see the polarizing nature of Detroit firsthand as you ride through areas that have seen little investment for decades and areas with homes that sell for millions.
This ride starts in Palmer Park, a large swath of green space that Thomas W. Palmer gifted to the city in the 1890s with the stipulation that the forest never be chopped down. Just south of the park, a dense residential area with apartment complexes grew, one of the only such places in Detroit today. Though some are still abandoned, the architecture here is unparalleled in terms of density. At one time, this area was home to Detroit’s LGBTQ+ community, which later left for cities like Ferndale.
From here, you’ll take Hamilton Avenue through Highland Park. If you aren’t aware, Highland Park is an entirely different city that Detroit (and a smidge of Hamtramck) completely surrounds. I’ve heard Hamilton called ‘Little Woodward’ on multiple occasions. Though Woodward does run through Highland Park, Hamilton was the lifeblood of many communities in the city, with many businesses, apartments, and stores lining the thoroughfare. Today, businesses are sparse; however, many historic buildings remain, including a stunning former antique store, the American State Bank of Highland Park (which later became a University of Islam), and the former Highland Park State Bank.
Just before passing Webb Street, you’re back in Detroit. There are more historic structures here, including one of my favorites, the former Detroit Savings Bank that later became Jaye Dee’s Mart. From here, you’ll turn onto Boston Boulevard, one of the finest residential streets in the city. Though this route only spends a short time in Boston Edison, it’s worth farting around this area for a bit if you enjoy old homes, as some of the city’s finest are in this area.
After enjoying the homes, you’re heading back uptown on 2nd Avenue. After reentering Highland Park, you’ll be greeted with numerous historic buildings when you cross Glendale Avenue. The former Highland Park High School looks like a castle rotting away, and the Glen-Vila Apartments are, somehow, still standing. The landscape turns somewhat industrial for a short time, and you’ll pass other unique but tattered buildings, like the William Ford & Company Showroom, which was a Fordson Farming Equipment showroom. As you continue up 2nd Avenue, you’ll pass through more neighborhoods before eventually dumping back into Palmer Park.
Once your ride is over, I recommend exploring the park (and its brand-new pickleball courts), getting a donut from Dutch Girl, or playing disc golf at the park’s course.
Dequindre Cut To Poletown East Ride
The Dequindre Cut is the most popular greenway in Detroit, and for good reason. It connects the Riverfront to Eastern Market and is a popular place to find Detroiters walking, getting miles in on their bikes, running, or hanging out with family and friends. We’ll start this ride by taking the Dequindre Cut from the Riverfront to Mack Avenue and continue from there. The Cut has a ton of murals, which are worth enjoying along the ride. People don’t always follow the lines on the path, so be careful for people in the bike lane.
Once you reach Mack Avenue, you’ll shimmy across the street onto St. Aubin. On your right is the track that used to extend to the Detroit River through the Dequindre Cut. You’ll see St. Albertus rising in the distance as you approach Canfield. You’ll go right by the parochial school it operated for decades and the former bank building across the street. From there, you’ll get closer to the neighborhood now called ‘Poletown East,’ which still has numerous historic structures.
On Forest Avenue, you’ll pass Dom Polski, a former Polish Hall home to community groups, events, and more. Once on Chene Street, the historic structures come thick and fast. To name a few, you’ll pass the Raven Lounge, the former Fredro/King Theatre, the Round Bar, Max’s Jewelry Store, Chene-Ferry Market, and Rosołowski Bridal Shop. From there, you’ll circle St. Stanislaus Roman Catholic Church, which still sits vacant. Continuing through the neighborhood, you’ll pass institutions like the All Saints Russian Orthodox Cathedral, Lipke/McDougall Hardware, and Saint Hyacinth Roman Catholic Church.
After turning onto Warren, you’ll pass two former cigar factories, which primarily employed Polish women and where sit-down strikes occurred in the 1930s. You’ll keep trucking through the neighborhood before returning to the Dequindre Cut and returning to where you started.
For more historical information on this neighborhood, check out every post on Poletown East.
Riverside Park To Delray Ride
Riverside Park is one of the finest parks in Detroit, thanks to recent renovations, and it’s a solid place to start your ride in Southwest Detroit because it offers ample parking, bathrooms, and great views of the Detroit skyline.
Leaving the park on Grand Boulevard, you’ll pass Fort Street, which offers another unique view of the city to the right. From there, you’ll pass the infamous Hotel Yorba, featured in a White Stripes song in 2001. From there, you’ll pass Clark Park and turn onto Clark Street, your portal into Delray.
After finding Clark Street’s terminus at Jefferson Avenue, you’ll see the now demolished Harbor Terminals Building site and the Detroit Copper & Brass Rolling Mills tattered remains. As you continue down Jefferson, you’ll pass historic Fort Wayne, which the City of Detroit has owned for decades. In the distance, the new Gordy Howe Bridge, which spans the Detroit River to Canada, rises above the landscape.
After passing the train tracks, you’re in what I call ‘downtown Delray,’ which is a shell of its former self but still holds plenty of history. The former Fox Hardware, built in the 1880s, still stands at the corner of Jefferson and West End across from a former bank building. The Gunsberg Building is another favorite, though it may have a demolition with the wrecking ball. Further down the road, you’ll see the Ideal Bar, a former post office, and various tattered remains of what Delray used to be. Probably the most unique of the bunch is St. John Cantius, a church surrounded by a wastewater treatment plant.
We’ll continue into the neighborhood, crossing into an area known as Carbon Works. Delray Tower still guards the entrance, though its future is unclear. You’ll pass the Carbon Athletic Club, one of Detroit’s truly most unique bars, though you must be a member to drink there. They’re friendly enough to let you in if they’re open, though! Backpedaling a bit, you’ll pass Holy Cross Catholic Church, a true jewel of Delray and Detroit.
Eventually, you’ll pop back onto Jefferson and pedal back the same way you came. This route takes you on Fort Street, which saves time but is a bit busy for some folks. If you prefer fewer cars, take the same path you took to avoid the hubbub of Fort Street.
For more historical information on this neighborhood, check out every post on Delray.
Belle Isle & Packard Plant Ride
Belle Isle is the perfect place to start any ride in Detroit because of it’s location and ample parking. Plus, it’s beautiful and offers a place to get miles in without much traffic on most days, which is an added bonus, and there’s enough history on the island alone to fill a few books.
Starting near Sunset Point, you’ll pass the Belle Isle Casino and Conservancy, which are both architecturally stunning. Further down the island, you’ll run into the Coast Guard Station, which is a reminder that the land you’ve been admiring across the water is, in fact, a different country. Near the island’s far side, you’ll see the William Livingstone Memorial Lighthouse peeking through the trees. Shockingly enough, there was once a military base here. However, that’s long gone, and it’s a lovely place to walk or ride a gravel bike now. Coming around the Detroit side of the island, you’ll pass the Belle Isle Yacht Club and Boat House, the latter of which had a brush with demolition early in 2024 but is stable for now. Leaving the island, you’ll cross the MacArthur Bridge, which opened in 1923.
Now that we’re on the mainland, you’ll pedal down Grand Boulevard for a few miles. This thoroughfare goes around what, at the time, was a growing city when construction first started in the 1890s. Detroit quickly expanded to make this more of an inner ring than an outer one, but some of Detroit’s finest homes were built on the Boulevard, as Detroiters call it, many of which still stand today. The only busy crossings you have to worry about on this part of Grand Boulevard are Jefferson and Gratiot.
While waiting at the light at Gratiot, you can admire East Grand Boulevard Methodist Church on your left, which was much further from the road before Gratiot was widened, and the Cathedral of St. Anthony Ecumenical Catholic Church, which rises in the distance. If you’re lucky, you’ll pass on the hour, and St. Anthony’s bells will be ringing.
Eventually, Grand Boulevard curves left, and you’ll be greeted by what’s left of the Packard Plant. For decades, the plant pumped out luxury cars; however, after Packard merged with Studebaker in 1953, the company folded a few years later, and the factory was parted out to smaller manufacturers and suppliers. It remained open until the late 1990s when the City of Detroit forced its closure and ultimate demise. It was vacant for years until wholesale demolition began in 2022. Pieces remain, but nothing close to how the structure once was.
As you cross the east side heading back to Belle Isle, you’ll pass a few more landmarks worth mentioning. The Pfeiffer Brewing Company’s facility still stands tall, though it’s been vacant for some time. Just down the road sits one of the first homes of the Hudson Motor Car Company, which has been for sale off and on in recent years. Most recently used as an art space, the Frederick M. Sibley Lumber Company Building is worth admiring, too.
The east side is a lovely place to pedal; however, every ride has to end eventually, and you’ll end this one by heading over the MacArthur Bridge and back onto Belle Isle.
My Cycling Gear:
If you order from a link below, I may receive a small commission at no charge to you.
My Bike Helmet:
Retrospec Retrospec Dakota Bike Helmet
I’ve been using the same Retrospec helmet for about five years, which means it’s probably about time to get a new one. In that time, I’ve ridden thousands of miles with it, fallen off my bike a handful of times, and been hit by one car. So far, so good. I’ll probably get the same one again!
My Front Bike Headlight:
Planet Bike Beamer 700 Bike Headlight
I got this light recently, so I can’t speak to its longevity, but it’s been good so far. It’s bright enough for riding at night in dark neighborhoods, and the modes are adequate for my needs cycling at night in Detroit. If you’ve got thick handlebars, it might not fit, so be sure to measure first.
My Bike Taillight:
Ascher Ultra Bright USB Rechargeable Bike Light Set
I purchased This combo pack with a front and rear light six years ago. I still have the front lamp and use it as a backup for a friend who needs to borrow one; however, I still use the taillight on every ride. It’s easy to use, the battery lasts ages, and it’s gotten dumped on by rain and pummeled with snow without breaking.
My Bike Lock:
Via Velo Bike U Lock with Cable
I’m not someone who will leave my bike anywhere; however, I do leave it locked up once every two weeks or so, and I always use this lock. Typically, I keep the lock and cable in a backpack or wear it around my waist. It isn’t the most portable, but nobody has tried breaking it yet, so I’ve got that going for me, which is good!
