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My partner and I are planning a long weekend trip for Labor Day this year (late August/early September 2024).
We live in Chicagoland and would like to take some time to explore more of the greater Midwest/Great Lakes region.
While we initially considered a trip to St Louis, Cleveland, Cincinnati, or Milwaukee - we agreed that Pittsburgh and Detroit are higher up on our list of places to see.
However, we are having difficulty deciding which of these 2 cities to chose.
We are considering Pittsburgh because it has one of the most unique geographic settings for a large city, it has fantastic residential and commercial architecture from it's days as a large and wealthy industrial city, stellar museums, a legacy public transit system, and plenty of neighborhoods that we would like to explore. We are also thinking of renting a car to see Falling Water outside Pittsburgh.
We are considering Detroit because it still has one of the largest concentrations of beaux art and art deco commercial architecture in the Midwest outside of Chicago. The downtown area looks like it has recovered quite a bit and we are thrilled to see that parts of the city are seeing so much investment. We would also love to explore Belle Isle, see the Henry Ford museum, the Pewabic tile shop, the Detroit Institute or the Arts, and perhaps cross the border to see Windsor, Ontario.
Our biggest concern regarding Detroit is if it has enough going on to fill a 4-5 day weekend. It seems like much more of Pittsburgh's historic urban areas have been left intact compared to Detroit. Regardless, we are interested in the history of both cities, and I would like to think we will the appreciate the architecture, museums, and neighborhoods of either option.
I would like to ask the Pittsburgh and Detroit locals on City Data which city they believe would be a better place to visit for a 4-5 day weekend?
Also, please let us know if there is anything else you might recommend for each city that I have not mentioned yet!
So, when Covid was wrapping up road tripping and exploring. Mind you, there WERE some disadvantages including things not being fully opened, so my experienced then will be different than today. I spent a a night and part of 2 days in each Pittsburgh and Detroit. I did NOT visit inside any museums I just got the lay of the land and explored architecture and what food I could.
In Detroit I was not able to visit Canada, and Belle Island was partially closed off by police. I was only able to see a small fraction and not able to park near anything. I stayed downtown, walked around and saw some sparks of what might be great things. There was some street level shopping on Woodward Ave I think, and I did like the Detroit Tigers stadium (several playful tiger statues outside. I drove up to the old Union Station that was being redeveloped. My overall impression was things were pretty spread out and there was no efficient public transit (and Uber was still a little shaky at that time).
Pittsburgh does have a very scenic setting, and a as a result of the rivers a compact downtown that is very Manhattan-esque. There I drove up to Grandview Ave for a wonderful view, and again toured the stadium areas. Things felt 'closer' there.
Not on your list, but I was impressed with Cleveland, the lake front, the Rock and Roll Hall of Fame (again, didn't go inside). I didn't stay in Cleveland, just walked around a little on the trip from Pitt to Detroit.
If you have not been to STL and want any recommendations please hit me up with things you like. I have been here over 20 years and feel I have a good idea of what the city has to offer.
Detroit and Pittsburgh are 2 cities I greatly admire.
Pittsburgh is more architecturally interesting, esp if you like some old Victorian buildings and houses -- the City just 'feels' very old. Pittsburgh is also more compact and walkable (and certainly more in-city trendy walkable neighborhoods like Southside, Shadyside/E. Liberty, Oakland and Squirrel Hill) and and is easier to navigate via public transportation and has the more interesting (very hilly) topography -- riding up Mount Washington on 1 of the 2 inclines to Grandview Ave, with it's grand view of the Golden Triangle and the 3 rivers, is a MUST...
... but I voted for Detroit. Why? Because overall, I feel Detroit has a tad more things to do, more stronger city heritage and more cultural and off-beat aspects. Downtown has made tremendous strides in terms of retail, restaurants and excitement, and the Campus Martius conversion in the middle of downtown, into an awesome public park has paid dividends.' Further up main-spine street, Woodward Ave, there's Midtown, with tons of restaurants, clubs, off-beat museums ... and and old-style, authentic bowling alley. Midtown and its up-city neighbor, New Center, have made tremendous comeback strides, again with much of what Midtown has to offer, plus the fabulous Detroit Inst. of Art, public library and scores of infill housing supplementing many grand old Victorian (very large) mansions; and is a livable, vibrant neighborhood. (NOTE: if you're staying downtown, ride the M-1 streetcar up Woodward to Midtown and New Center; it's fun, convenient with frequent service, and who needs a car, anyway?)
Of course there's all the auto factories of Motown; as of a few years ago, you could arrange a tour of them, which is a priceless experience...
And then there's the music tradition. I tour of Hitsville, Motown music's birthplace on Grand Blvd, is an afternoon's worth in itself. Then, by evening, check out the many great jazz clubs, the most famous being Baker's Keyboard Lounge at the northern edge of the City -- a proving ground of jazz artists since 1934 and a launchpad of some of America's most renowned Jazz musicians -- Baker's used to stay open practically all night on weekends; and the food there is very good, too.
Of course you can spend several days at Greenfield Village in nearby Dearborn, with its ton of exhibits, food and tours. Families and kids love it. Huge, vibrant Eastern Market is a place for which Pittsburgh has no answer, is also a great way to spend a warm, Labor Day weekend afternoon. Belle Isle, the beautiful Island park in the Detroit River, just east of downtown, is an awesome place, too... And for great walk, vibrant areas, check out Greektown in downtown and, esp, Royal Oak, just north of the City...
And there's much more to Detroit, so check it out.
Detroit and Pittsburgh are 2 cities I greatly admire.
Pittsburgh is more architecturally interesting, esp if you like some old Victorian buildings and houses -- the City just 'feels' very old. Pittsburgh is also more compact and walkable (and certainly more in-city trendy walkable neighborhoods like Southside, Shadyside/E. Liberty, Oakland and Squirrel Hill) and and is easier to navigate via public transportation and has the more interesting (very hilly) topography -- riding up Mount Washington on 1 of the 2 inclines to Grandview Ave, with it's grand view of the Golden Triangle and the 3 rivers, is a MUST...
... but I voted for Detroit. Why? Because overall, I feel Detroit has a tad more things to do, more stronger city heritage and more cultural and off-beat aspects. Downtown has made tremendous strides in terms of retail, restaurants and excitement, and the Campus Martius conversion in the middle of downtown, into an awesome public park has paid dividends.' Further up main-spine street, Woodward Ave, there's Midtown, with tons of restaurants, clubs, off-beat museums ... and and old-style, authentic bowling alley. Midtown and its up-city neighbor, New Center, have made tremendous comeback strides, again with much of what Midtown has to offer, plus the fabulous Detroit Inst. of Art, public library and scores of infill housing supplementing many grand old Victorian (very large) mansions; and is a livable, vibrant neighborhood. (NOTE: if you're staying downtown, ride the M-1 streetcar up Woodward to Midtown and New Center; it's fun, convenient with frequent service, and who needs a car, anyway?)
Of course there's all the auto factories of Motown; as of a few years ago, you could arrange a tour of them, which is a priceless experience...
And then there's the music tradition. I tour of Hitsville, Motown music's birthplace on Grand Blvd, is an afternoon's worth in itself. Then, by evening, check out the many great jazz clubs, the most famous being Baker's Keyboard Lounge at the northern edge of the City -- a proving ground of jazz artists since 1934 and a launchpad of some of America's most renowned Jazz musicians -- Baker's used to stay open practically all night on weekends; and the food there is very good, too.
Of course you can spend several days at Greenfield Village in nearby Dearborn, with its ton of exhibits, food and tours. Families and kids love it. Huge, vibrant Eastern Market is a place for which Pittsburgh has no answer, is also a great way to spend a warm, Labor Day weekend afternoon. Belle Isle, the beautiful Island park in the Detroit River, just east of downtown, is an awesome place, too... And for great walk, vibrant areas, check out Greektown in downtown and, esp, Royal Oak, just north of the City...
And there's much more to Detroit, so check it out.
Thank you for replying!! I really appreciate your suggestions!
After reading your post I think I am leaning towards Detroit now. It is a place that my partner and I have discussed visiting together since we first met. We will be sure to check out any factory tours and architecture walking tours. I still plan on visiting Pittsburgh as well but it will probably be the following year (2025) I think. Thanks again!
I like both cities, but if you go with Detroit and you're both cyclists, I'd recommend going by train and getting a bicycle reservation and potentially doing a stopover or one day and night in Ann Arbor.
Oh, that is my other question! What is the best way to get around Detroit?
Is it best to rent a car or can we rely on bike share/public transit?
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