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Voted Chicago, but it feels like the criteria were picked specifically to give the city an edge. Most of them scale pretty linearly with city size, and Chicago is a clear step up from Boston in that regard.
Nightlife I would expect Chicago to have a huge lead because Boston's nightlife is particularly bad (and Chicago's is great), but in terms of shopping, events, and other entertainment I would think they'd be pretty competitive because the metro area sizes aren't that different.
Honest question because outside of common knowledge about the city, I'm not an expert on Boston. Does Boston have any events that mirror the popularity/prominence of Lollapalooza, Taste of Chicago, or the Air and Water show?
Honest question because outside of common knowledge about the city, I'm not an expert on Boston. Does Boston have any events that mirror the popularity/prominence of Lollapalooza, Taste of Chicago, or the Air and Water show?
Boston marathon is a big internationally known event..there are music festivals, harborfest, Oktoberfest, food and wine tastings, pride parades, tall ships, that Chicago has as well..no music events as large as lolla..the head of the Charles is event on river for colleges competing in rowing etc..beanpot is local competition for area college hockey programs....Boston also does events commemorating historical events.Chicago’s size will allow for more events without a doubt..regarding the thread Chicago as a city offers more from standpoint of amenities- restaurants, events etc...Boston will win in areas like history, research, education, medicine, and if people subjectively prefer regional location closer to mountains, ocean, nyc etc
Honest question because outside of common knowledge about the city, I'm not an expert on Boston. Does Boston have any events that mirror the popularity/prominence of Lollapalooza, Taste of Chicago, or the Air and Water show?
Boston's biggest Annual Events:
Boston Calling (a bit surprised you've never heard of it as it's one of the 15-20 largest music festivals in the US now, but it takes a back seat to the more substantial and traditional music festivals like Lolla no doubt)
Boston Marathon (it's bigger than the Air and Water Show, believe it or not)
Feast of Saint Anthony (google image it)
Head of The Charles (as it's known, The Regatta, which you may be familiar with)
Boston Harborfest
And above all else, Boston Pops 4th of July
There is no Lollapalooza equal. This is the runaway event comparatively.
The Air and Water show is cool, but it's certainly not internationally known, probably not even well known to those outside of the neighboring States. I think most folks minds go to San Diego when they hear Air and Water Show. I've never heard of anyone outside of the Midwest refer to the Taste of Chicago, either.
The biggest stand out for Chicago is the weekend series of neighborhood/street festivals. I can't think of any other city that does anything that substantial, that regularly. While Chicago packs in folks in the summer, Boston is quite the opposite.. Generally, Bostonians are everywhere but Boston on summer weekend. Cape Cod, the Islands, Newport, Portsmouth, Portland, Lake Sebago, Lake Winnipesaukee, Block Island, etc.
Boston marathon is a big internationally known event..there are music festivals, harborfest, Oktoberfest, food and wine tastings, pride parades, tall ships, that Chicago has as well..no music events as large as lolla..the head of the Charles is event on river for colleges competing in rowing etc..beanpot is local competition for area college hockey programs....Boston also does events commemorating historical events.Chicago’s size will allow for more events without a doubt..regarding the thread Chicago as a city offers more from standpoint of amenities- restaurants, events etc...Boston will win in areas like history, research, education, medicine, and if people subjectively prefer regional location closer to mountains, ocean, nyc etc
I will give you the Boston marathon, totally forgot about that.... I would still say Chicago wins on the events front, and not only because it's bigger. NYC is bigger than Chicago yet doesn't have a music festival like Lolla. I agree with you that Boston wins on fronts such as history, higher ed, less crime, uniqueness, scenery. I'd say one thing Chicago and Boston both dominate the rest of the country with is sports. IMO, the best pro sports cities in the country.
Boston's biggest Annual Events:
Boston Calling (a bit surprised you've never heard of it as it's one of the 15-20 largest music festivals in the US now, but it takes a back seat to the more substantial and traditional music festivals like Lolla no doubt)
Boston Marathon (it's bigger than the Air and Water Show, believe it or not)
Feast of Saint Anthony (google image it)
Head of The Charles (as it's known, The Regatta, which you may be familiar with)
Boston Harborfest
And above all else, Boston Pops 4th of July
There is no Lollapalooza equal. This is the runaway event comparatively.
The Air and Water show is cool, but it's certainly not internationally known, probably not even well known to those outside of the neighboring States. I think most folks minds go to San Diego when they hear Air and Water Show. I've never heard of anyone outside of the Midwest refer to the Taste of Chicago, either.
The biggest stand out for Chicago is the weekend series of neighborhood/street festivals. I can't think of any other city that does anything that substantial, that regularly. While Chicago packs in folks in the summer, Boston is quite the opposite.. Generally, Bostonians are everywhere but Boston on summer weekend. Cape Cod, the Islands, Newport, Portsmouth, Portland, Lake Sebago, Lake Winnipesaukee, Block Island, etc.
Really the only truly national event Boston has is the marathon (in terms of public consciousness). Regata is a big deal, but let's be honest, it's quite niche. Nobody outside of New England really cares about any of those other events.
I think the midwest has a much stronger street festival culture going on. I've been overwhelmed by the sheer amount of them happening in Cleveland in just the last couple weeks.
Really the only truly national event Boston has is the marathon (in terms of public consciousness). Regata is a big deal, but let's be honest, it's quite niche. Nobody outside of New England really cares about any of those other events.
I think the midwest has a much stronger street festival culture going on. I've been overwhelmed by the sheer amount of them happening in Cleveland in just the last couple weeks.
I'd say the Marathon and the Fourth of July/Pop's is a big deal. Boston Calling, for the younger generation, is too. But yes, most are local/regional much like Taste of Chicago (which was largely my point).
Agreed on the street festival culture. It's pretty amazing.. Certainly something I'd love for Boston to do, but I'm sure parking/NIMBYism prevails here. I'd love to see Allston/Brighton Ave weekend festival, a Union Square festival, a Central Sq festival, a Seaport Blvd festival. Chicago's rotating weekend neighborhood events are killer.
I do wish, however, Chicago would start doing the outdoor brewery beer gardens along the waterfront/parks/unused space. I suppose they don't need to, as almost every bar has their own beer garden.
My two hometowns. My two favorite cities not named NYC.
quality of life: Boston
nightlife: Chicago
restaurants: Chicago
events: Chicago
transit: Chicago
shopping/entertainment: Chicago
overall vibe of city and people: Boston
What may surprise many is just how close most of these categories are (have to include Cambridge/Somerville/Brookline). I think events, shopping, and entertainment are pretty close. There's a ton going on in both cities.. Plenty of live music venues, plenty of utilized open space, plenty of food halls and markets, breweries, open water.
Chicago is a far more dynamic city on the whole. Way more substantial downtown core that no other city can really rival. Some of the countries most interesting neighborhoods west of 94. A larger focus, even as a %, in arts/music. A more diverse populous. Just a more bad*ss city on a macro level. But on a micro level, I liked living in Cambridge more than I liked living in Lincoln Park.. Far more interesting, more eclectic, a little more day-to-day buzz, better food. I certainly like Boston's surroundings far more than Chicago's, that is for sure.
I like the day-to-day feel in Boston more. A bit less hectic, more widely accessible, a nicer city to walk around, a really diverse set of areas to spend your time.. Love the farm-to-table, coffee and beer scene, which to be fair, takes up a lot of my free time these days. What I like about Boston certainly expands to the suburbs, too. And the suburbs, and coastal towns make it a far more charming and unique place to be.
As I always do, vote goes to Chicago (city) and Boston (area).
I enjoy reading your posts and you seem like a knowledgeable and objective poster. I find it curious though that you talk up Chicago so much but at the same time say that you enjoyed living in Boston more. So what gives?
Whenever Chicago is compared to “lesser” cities, it is always “Chicago is bigger” etc etc. That’s also consistent with my real life experience with people who have lived in Chicago — they have a uniformly high opinion of the city, but when you try to dig in a little it always comes down to the same thing — “Chicago is bigger so there is more of everything.” Boston, OTOH, is “small, overrated and overpriced”.
I am sure there is something to it if everyone says it (and of course we do know that Chicago is much more affordable and has better nightlife — there is no question about that) but if we go a little more “micro” (in your words) and compare the areas of each city that a typical resident/young professional is actually likely to be exposed to day-to-day, is there really a big size disparity that supports this default assumption that “Chicago has more of everything”? No agenda, just an honest question. So if you compare, say:
Downtown Chicago + West Loop + Old Town/GC + LP + LV + WP + Bucktown + Logan Square
VS
Downtown Boston + North End + Beacon Hill + Back Bay + South End + Seaport District & South Boston + Fenway-Kenmore + Cambridge
[feel free to add any other happening areas I missed out]
Does Chicago clearly come out on top in that comparison? If so why and where? I am not particularly interested in once a year music festivals, but more in the day-to-day — street buzz, cool bars/restaurants/coffee shops, quality and accessibility of public transportation and the ease of getting around, etc.
I enjoy reading your posts and you seem like a knowledgeable and objective poster. I find it curious though that you talk up Chicago so much but at the same time say that you enjoyed living in Boston more. So what gives?
Whenever Chicago is compared to “lesser” cities, it is always “Chicago is bigger” etc etc. That’s also consistent with my real life experience with people who have lived in Chicago — they have a uniformly high opinion of the city, but when you try to dig in a little it always comes down to the same thing — “Chicago is bigger so there is more of everything.” Boston, OTOH, is “small, overrated and overpriced”.
I am sure there is something to it if everyone says it (and of course we do know that Chicago is much more affordable and has better nightlife — there is no question about that) but if we go a little more “micro” (in your words) and compare the areas of each city that a typical resident/young professional is actually likely to be exposed to day-to-day, is there really a big size disparity that supports this default assumption that “Chicago has more of everything”? No agenda, just an honest question. So if you compare, say:
Downtown Chicago + West Loop + Old Town/GC + LP + LV + WP + Bucktown + Logan Square
VS
Downtown Boston + North End + Beacon Hill + Back Bay + South End + Seaport District & South Boston + Fenway-Kenmore + Cambridge
[feel free to add any other happening areas I missed out]
Does Chicago clearly come out on top in that comparison? If so why and where? I am not particularly interested in once a year music festivals, but more in the day-to-day — street buzz, cool bars/restaurants/coffee shops, quality and accessibility of public transportation and the ease of getting around, etc.
I think "having more" because the city is 2x larger really is the only argument. If you shrank Chicago and Boston to the inner 20-25 sq miles they would be similar but after that Chicago has far more neighborhoods while Boston has places like Waltham and West Roxbury which are really only Semi-urban.
However I think people just give Chicago the Transit win when if you look at actual ridership the MBTA has a higher transit share in the metro area and there is actual connection between Commuter rail and subway access while in Chicago you have to walk a couple blocks from Union Station to the L.
I think "having more" because the city is 2x larger really is the only argument. If you shrank Chicago and Boston to the inner 20-25 sq miles they would be similar but after that Chicago has far more neighborhoods while Boston has places like Waltham and West Roxbury which are really only Semi-urban.
However I think people just give Chicago the Transit win when if you look at actual ridership the MBTA has a higher transit share in the metro area and there is actual connection between Commuter rail and subway access while in Chicago you have to walk a couple blocks from Union Station to the L.
Yeah I get that if you like cities you’d rather be in Edgewater or Lincoln Square than West Roxbury, but it’s not like someone who lives in River North or Wicker Park would have any reason to go to Edgewater.
I guess what I wanna know is if we just look at the inner ~30 sq miles or so — which I believe is where most people living in the urban core will spend the vast majority of their time — what does Chicago do (other than nightlife) appreciably better in terms of things that are relevant to day-to-day urban experience (eg cool neighborhoods, restaurants/bars, street vibrancy, interesting people, public transit and ease of getting around, urban character etc)? Or is it just that Chicago’s urbanity stretches much farther so there is simply more “stuff” over a larger area ... and that’s really it?
Last edited by Fitzrovian; 09-11-2019 at 05:55 PM..
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