MY TOP 15 NEW ENGLAND CITIES

1. Pittsfield
2. Lawrence
3. Pawtucket
4. Springfield
5. Holyoke
6. Haverhill
7. New Bedford
8. Fall River
9. Fitchburg
10. Brockton
11. Lynn
12. Saugus
13. Chelsea


Elite world class cities. One even has a major sport's hall of fame, and another will even be the site of the New England FBI headquarters.

I concur.
 
I agree. I'm sensitive with New Bedford because it's not exactly highly reputed (especially locally). I love the look/feel of the downtown area and it's boom (quietly, I might add. NB takes a back seat to PVD and BOS in the media) over the past 5 years is nothing short of impressive. 40 new storefronts downtown (including a new waterfront hotel), and 30% increase in seaport cargo in a down economy is good news.. It's about to undergo a $50+ Million dollar expansion and be the biggest staging area for offshore wind technology in the country. It is, of course, "homadafish" and it has had the highest grossing fishing fleet in the nation for 10 years running. It's finally a city that's starting to come into its own. Maybe it'll be higher up in a few years.



.

Don't forget about the 17.4 million dollar New Bedford Regional Airport (EWB) runway improvement/expansion project that broke ground last month.
 
Due to the recent release of the 2010 census figures, I am considering moving Providence to the 2 spot and dropping Hartford down to number 3. Hard to believe that Hartford is now the third largest city in Connecticut after Bridgeport and New Haven. I'll have my people keep you informed! Actually had the day off today and boredom has set in due to the weather :)
 
My 2012 revised rankings of New England cities:

1. BOSTON, 2. PROVIDENCE, 3. HARTFORD, 4. SPRINGFIELD, 5. WORCESTER, 6. NEW HAVEN, 7. PORTLAND, 8. MANCHESTER, 9. BRIDGEPORT, 10. NEW BEDFORD/FALL RIVER, 11. LOWELL/LAWRENCE, 12. STAMFORD, 13. BURLINGTON, 14. WATERBURY/DANBURY, 15. BANGOR

After visiting most of these cities during the past year and a half, felt it was time to shuffle the deck and reconsider my rankings due to recent changes and proposed developments in the New England urban landscape.

Some of my adjustments and reasoning are as follows: Providence and Hartford are a dead heat in most judging categories but I now feel that Providence is moving forward and Hartford is remaining where it has been for the last 5 years. Providence has a port and it's coastal location has won me over for this round. Springfield and Worcester are still a close call but I feel Worcester is too connected to Boston and Springfield may be moving forward with a major casino project downtown and it at least shares a major airport with Hartford.

If New Haven had a competitive airport and an arena it would have moved up a spot or two. My hometown and Manchester is another coin toss but Portland is currently hot with projects underway and an amazing list of proposed downtown developments that could be the envy of all but the largest of New England cities. Even if some of the projects never break ground, there are enough in the plans to considerably improve the landscape and to have a Westin hotel downtown is a huge boost to the city.

Bridgeport is just plain depressing but too large to ignore. It deserves some credit for trying and does have an impressive arena, AA ballpark and a major bank is headquarterd there. Added Stamford to the list after a recent visit. Though I still feel it is more connected to New York than Connecticut, it has become too big of a player in the corporate world to be thrown to the side.

Combined New Bedford/Fall River along with Waterbury/Danbury because it just made good sense to me. No offense, but Waterbury still has that "lost in the seventies" feeling to it more than any other sizable New England city. Burlington and Bangor survive due to their importance as regional hubs which also helps Portland in the rankings. Had to take Pittsfield for a long drive in the country which is where it is located anyway, breaking up is hard to do!

Honorable mention goes out to New London, Lewiston, Nashua, Newport and of course Pittsfield, they are not ready for prime time just yet. Remember that these are my personal rankings and opinions and I always enjoy a good debate with my fellow urbanologists.
 
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My 2012 revised rankings of New England cities:

1. BOSTON, 2. PROVIDENCE, 3. HARTFORD, 4. SPRINGFIELD, 5. WORCESTER, 6. NEW HAVEN, 7. PORTLAND, 8. MANCHESTER, 9. BRIDGEPORT, 10. NEW BEDFORD/FALL RIVER, 11. LOWELL/LAWRENCE, 12. STAMFORD, 13. BURLINGTON, 14. WATERBURY/DANBURY, 15. BANGOR

After visiting most of these cities during the past year and a half, felt it was time to shuffle the deck and reconsider my rankings due to recent changes and proposed developments in the New England urban landscape.

Some of my adjustments and reasoning are as follows: Providence and Hartford are a dead heat in most judging categories but I now feel that Providence is moving forward and Hartford is remaining where it has been for the last 5 years. Providence has a port and it's coastal location has won me over for this round. Springfield and Worcester are still a close call but I feel Worcester is too connected to Boston and Springfield may be moving forward with a major casino project downtown and it at least shares a major airport with Hartford.

If New Haven had a competitive airport and an arena it would have moved up a spot or two. My hometown and Manchester is another coin toss but Portland is currently hot with projects underway and an amazing list of proposed downtown developments that could be the envy of all but the largest of New England cities. Even if some of the projects never break ground, there are enough in the plans to considerably improve the landscape and to have a Westin hotel downtown is a huge boost to the city.

Bridgeport is just plain depressing but too large to ignore. It deserves some credit for trying and does have an impressive arena, AA ballpark and a major bank is headquarterd there. Added Stamford to the list after a recent visit. Though I still feel it is more connected to New York than Connecticut, it has become too big of a player in the corporate world to be thrown to the side.

Combined New Bedford/Fall River along with Waterbury/Danbury because it just made good sense to me. No offense, but Waterbury still has that "lost in the seventies" feeling to it more than any other sizable New England city. Burlington and Bangor survive due to their importance as regional hubs which also helps Portland in the rankings. Had to take Pittsfield for a long drive in the country which is where it is located anyway, breaking up is hard to do!

Honorable mention goes out to New London, Lewiston, Nashua, Newport and of course Pittsfield, they are not ready for prime time just yet. Remember that these are my personal rankings and opinions and I always enjoy a good debate with my fellow urbanologists.

My top five: Boston/Cambridge, Providence, Portland, Burlington, Portsmouth. Don't really care about the other places, and I don't think they garner much attention really as destinations. But that's not to say that's the only way this list could be ranked--just the way I'm ranking it. We could do it by population, by business importance, etc., in which case places like Bridgeport, Worcester, Lewiston, Bangor get included by virtue of the fact that they exist, and places like Hartford get included because they are employment/business centers. But for urban centers, I think there are probably only those five above that people really come to see. I know other cities have pockets here and there, but the five I listed are all around great places to visit in most people's opinion--the other New England cities don't have the same reputation for whatever reason. Worcester should be ranked higher in my opinion because last I knew it was the fastest growing metro area (micro metro) in the State. There are also a bunch of smaller places that are all around more enjoyable and attractive than many of the bigger cities. The trick is how to bring the quality urbanism to the quantity based urban centers.
 
If the list is supposed to be "urban places of interest to tourists", I agree with your top five, but I'd round out the list with: Newport, Salem (MA), Gloucester, Newburyport, Lowell, New Bedford, Northampton*, and Brattleboro (yes, it's tiny, but it's quite urban).

* should we lump Amherst in with it? They aren't abutting neighbors.
 
My top five cities for for tourists: 1. BOSTON, 2. PORTLAND, 3. BURLINGTON, 4. PORTSMOUTH, 5. NEWPORT

Honorable mention includes Hyannis, Provincetown, Newburyport and New London. Rutland may win the winter award due to it's proximity to the ski resorts.
 
If the list is supposed to be "urban places of interest to tourists", I agree with your top five, but I'd round out the list with: Newport, Salem (MA), Gloucester, Newburyport, Lowell, New Bedford, Northampton*, and Brattleboro (yes, it's tiny, but it's quite urban).

* should we lump Amherst in with it? They aren't abutting neighbors.
I don't think that was the original intent but just how I think of importance. Also for small places Exeter NH and Freeport and Camden Maine.
 
Freeport struck me as a huge outlet mall overlaid on the street grid of what used to be a real town.
 
I consider Freeport as part of Portland. just like I do with the Maine Mall area.

Portsmouth is a stand alone town and a great one at that.

I haven't been to Bangor in fifteen years but it seems to be on the most improved list if there was one.
 
Is Portsmouth really a bigger tourist draw than Newport RI? I'd consider Newport a bigger destination than Portsmouth but that could be because that's where I spend more time.
 
Lrfox, I at least put Newport in my top five!

I know! It's fine since it's a matter of personal opinion. Still, I would think that if the criteria was "urban places of interest to tourists" I'd put Newport ahead of Portsmouth. If it's cities you'd choose to live in, it doesn't even matter if you put Holyoke MA over Boston! I think between the beaches, the Mansions/Bellevue Avenue, Cliff Walk, the International Tennis Hall of Fame, the fact that Newport is one of the greatest sailing towns in the country, and the shopping, dining and nightlife downtown, I think it's a much bigger tourist draw than Portsmouth.

I've spent a grand total of 5 nights in Portsmouth over the past 8 years. So to put it mildly, I am not nearly as familiar with Portsmouth as I am Newport (I spend about 3 weekends every summer there at least) so my perception is probably skewed.
 
I know! It's fine since it's a matter of personal opinion. Still, I would think that if the criteria was "urban places of interest to tourists" I'd put Newport ahead of Portsmouth. If it's cities you'd choose to live in, it doesn't even matter if you put Holyoke MA over Boston! I think between the beaches, the Mansions/Bellevue Avenue, Cliff Walk, the International Tennis Hall of Fame, the fact that Newport is one of the greatest sailing towns in the country, and the shopping, dining and nightlife downtown, I think it's a much bigger tourist draw than Portsmouth.

I've spent a grand total of 5 nights in Portsmouth over the past 8 years. So to put it mildly, I am not nearly as familiar with Portsmouth as I am Newport (I spend about 3 weekends every summer there at least) so my perception is probably skewed.

I am aware of Newport, but haven't ever been. I guess it's too far outside my range of familiarity (Boston north). So, like you, perception is skewed. Out of curiosity, I googled how many visitors Newport gets annually, and it was 3.5 million. I once heard Freeport, Maine had the most visitors annually in Maine, at 3 million. I couldn't find any stats for Portland or Portsmouth.
 
My top five cities for for tourists: 1. BOSTON, 2. PORTLAND, 3. BURLINGTON, 4. PORTSMOUTH, 5. NEWPORT

I'd personally reorder it slightly: 1. BOSTON, 2. PORTLAND, 3. PORTSMOUTH, 4. BURLINGTON, 5. NEWPORT

Admittedly, I'm far less familiar with Newport than the other four, but it seems like the logical fifth. Downtown Portsmouth, to me, is more interesting and feels more immediately urban than Church St in Burlington. So I'd say it's better as an urban city for tourists with a more interesting city center, though I think Burlington has a relatively stronger sense of neighborhoods and urban amenities outside the downtown. Portsmouth seems to be improving in that regard, with a growing neighborhood center feeling along Islington St west of downtown, and in Kittery Foreside just east of downtown (albeit technically in a different town and state).

Still, as much as I love Portsmouth, I don't think measuring tourist-friendliness is the best way to weigh New England cities, just as I don't think looking purely at employment centers is. I don't think you were saying that it was; just wanted to make the point that there has to be some combination of the urban dynamism that attracts tourists (not to mention students and retirees), along with employment centers, urban amenities, livable and walkable neighborhoods, and so on. That's why, as much as I love Portsmouth, and as much of an employment center as Hartford is, I don't think I'd put either of them alone on my list of top five New England cities.

It's probably cheating a bit, but my (current, and ever-shifting) take on the top six New England cities, based on the combination of elements I listed above would be:

1. Cambridge/Boston
2. Portland
3. Manchester/Nashua/Portsmouth
4. Providence
5. Burlington
6. Hartford/New Haven


A lot of those could easily shift--sometimes I think I like Portland more the Cambridge/Boston (I definitely like the density and series of nodes in Cambridge more than Boston, so I list it first), and 3 & 4, as well as 5 & 6 could each switch places with each other in my book.

I also took the liberty of combining somewhat distant, but connected places like Hartford and New Haven, and less distant Manchester and Nashua together. Neither set of cities are as close as Boston and Cambridge, but if they work together (and become better linked through transit and planning), I think they could become much more cohesive and form a stronger, single urban area with two distinct nodes.

And I took the greater liberty of linking Manchester/Nashua and Portsmouth (about the same distance as New Haven and Hartford, but definitely less connected). It will take a lot more to link Manchester and Portsmouth than it will to link Manchester and Nashua, but despite its smaller size and more distant location, I think Portsmouth is the only city than can rival Manchester within New Hampshire. Like New Haven and Hartford, both have their strengths (economic center, upstarts in the Millyard, urban neighborhoods in Manchester; an incredibly vibrant downtown and greater sense of community in Portsmouth) and weaknesses (sort of the inverse of the strengths). Taken together, they'd be an incredible city (Portland?), and as it is, it's cheating to consider them as one, but I'd like to see Manchester/Nashua work together, and link more with Portsmouth.

I know! It's fine since it's a matter of personal opinion. Still, I would think that if the criteria was "urban places of interest to tourists" I'd put Newport ahead of Portsmouth. If it's cities you'd choose to live in, it doesn't even matter if you put Holyoke MA over Boston! I think between the beaches, the Mansions/Bellevue Avenue, Cliff Walk, the International Tennis Hall of Fame, the fact that Newport is one of the greatest sailing towns in the country, and the shopping, dining and nightlife downtown, I think it's a much bigger tourist draw than Portsmouth.

I've spent a grand total of 5 nights in Portsmouth over the past 8 years. So to put it mildly, I am not nearly as familiar with Portsmouth as I am Newport (I spend about 3 weekends every summer there at least) so my perception is probably skewed.

I haven't been to Newport in many years, and I go to Portsmouth several times a year, as I love the city and my mother now lives just outside Portsmouth. So my perception is also skewed.

The Cliff Walk, mansions, Tennis Hall of Fame and sailing are all big draws, for sure, but they aren't inherently urban--in fact, the Cliff Walk and mansions are decidedly un-urban, despite their relative proximity to downtown Newport. I'd argue that Portsmouth's main draws--dining, nightlife, entertainment, and even the Strawbery Banke history museum (a preserved neighborhood adjacent to downtown) are more urban-focused.

Now, I'm sure Newport has plenty of dining and nightlife downtown, as well, but in my recollection--and I may be totally wrong--Newport lacked any one area with the urban vibrancy of Market Square in Portsmouth. In my mind, that's one of the best urban spaces in New England; personally, I'd put Market Square ahead of any one space in even Portland, Boston or Providence, though those cities are certainly more urban overall.
 
I am aware of Newport, but haven't ever been. I guess it's too far outside my range of familiarity (Boston north). So, like you, perception is skewed. Out of curiosity, I googled how many visitors Newport gets annually, and it was 3.5 million. I once heard Freeport, Maine had the most visitors annually in Maine, at 3 million. I couldn't find any stats for Portland or Portsmouth.

I'm actually surprised Freeport is the top visited town in Maine. I would have just assumed Portland or Bar Harbor (maybe even Camden or Ogunquit). But I guess Freeport's status as a hybrid town/ outlet mall would make it a year-round destination (I know buses go up from MA all year round) whereas Portland and Bar Harbor would see stronger fluctuations in visitors with the seasons.

I haven't been to Newport in many years, and I go to Portsmouth several times a year, as I love the city and my mother now lives just outside Portsmouth. So my perception is also skewed.

The Cliff Walk, mansions, Tennis Hall of Fame and sailing are all big draws, for sure, but they aren't inherently urban--in fact, the Cliff Walk and mansions are decidedly un-urban, despite their relative proximity to downtown Newport. I'd argue that Portsmouth's main draws--dining, nightlife, entertainment, and even the Strawbery Banke history museum (a preserved neighborhood adjacent to downtown) are more urban-focused.

Now, I'm sure Newport has plenty of dining and nightlife downtown, as well, but in my recollection--and I may be totally wrong--Newport lacked any one area with the urban vibrancy of Market Square in Portsmouth. In my mind, that's one of the best urban spaces in New England; personally, I'd put Market Square ahead of any one space in even Portland, Boston or Providence, though those cities are certainly more urban overall.

I don't know if I'd go so far as to call those things anti-urban. Bellevue Avenue (where most of the mansions are centered) is not necessarily "urban" because the houses (estates, really) take up so much square footage and have well manicured lawns, etc. However, it's not anti-urban either. It's merely a few blocks from the city center, it's walkable (part of the draw of the mansions is that they're all spaced out in city blocks within walking distance from each other). Bellevue Ave. is a wealthy streetcar suburb on steroids in that you have single family homes within a typical urban grid that are all close to the core of the city. Not unlike the Western Promenade in Portland's West End or the houses along the Jamaicaway near Jamaica Pond in Boston. The caveat is that the homes in Newport are MUCH larger. Still, at worst it's suburban and it's the kind of suburban that we all appreciate in cities.

The Cliff Walk isn't urban because it's a natural feature, but given the proximity to downtown Newport, I'd say it's something akin to a great city park which is essentially urban. Public spaces are part of any city's urban appeal and the Cliff Walk is part of Newport's. I'd throw it in the same category as the Eastern and Western Promenade in Portland, Emerald Necklace in Boston (outside of Central Bosoton), or the Presidio in San Francisco. It's not a central urban park, but it's a great natural feature in an urban environment.

The Tennis Hall of Fame is easily the most urban of the bunch. It's a museum/arena cluster in an urban part of town. In fact, The exterior of the THoF is retail and dining space coming right up to the sidewalk (google maps). I don't see how it's any different from a place like Fenway Park except that it draws people in on a regular basis (because of the museum) instead of just sporting/concert events.

We're definitely on the same page re: Market Square in Portsmouth. I don't know if it's my favorite urban space in New England (I've always had a soft spot for North Square in Boston), but I'd say it's better than any one spot in Newport, Portland, or Burlington too. That said, I think you'd find similar urban vibrancy on Thames Street in downtown Newport and maybe even more so on Bannister's Wharf (easily one of my top 5 urban spots in New England). Still, The cohesiveness of downtown Portsmouth, in my mind, beats the others.

I'd also say that Spring Street (take a virtual stroll on google maps) and the intersecting streets remind me a lot of Portsmouth's Strawberry Bank and Washington Square and Trinity Park are as good as any central urban park anywhere.

Out of Portland, Portsmouth, Newport and Burlington, I'd say that Portland easily has the best restaurant scene of the bunch. I don't know which I'd give 2nd place to because I haven't dine in Burlington or Portsmouth enough to compare to NPT. For nightlife, it's got to be Newport for me. But again, I've only gone out extensively in Newport and Portland of that bunch (last time I went out in Portsmouth, you could smoke in bars). Newport has a great collection of bars downtown and just beyond(more than most cities 3x its size). Many of them are right on the water. One of my favorite Irish Pubs anywhere (Buskers) is in Newport. And while Newport's bar scene is clustered together so you can really walk to any of them, you get different atmospheres depending on which direction you go. Downtown bars are typically a little more "yuppy" (with some exceptions) while Lower Thames (South of Memorial blvd) has a more local scene. Broadway, just north of Washington Square has much more of that granola, artsy vibe. I'd also give the edge to Newport for shopping too since it has a large representation of both local and national brands. More so than the other three.

If we're talking simply attractive to tourists, I'd probably go like this:
1) Boston/Cambridge
2) Portland area (inc. Freeport, Cape Elizabeth, etc)
3) Newport
4) Burlington
5) Portsmouth

Now, if we're using this criteria "there has to be some combination of the urban dynamism that attracts tourists (not to mention students and retirees), along with employment centers, urban amenities, livable and walkable neighborhoods, and so on.", my list would be as follows:

1)Boston/Cambridge (easy)
2) Providence- enough merit to make it a great city on its own, but proximity to Boston is a huge bonus
3)New Haven- a lot of people discount CT, but New Haven is very much a New England that happens to be on major transit corridors- I-95, Amtrak, Metro North, I-91, etc.
4)Portsmouth- On its own, Portland would get the edge in my opinion. But Portsmouth has a lot going for it independently with the added bonus that it's a reasonable commute to Boston from Portsmouth.
5) I'd put Portland or Stamford here. Stamford has a lot of shopping/dining downtown, it's on the coast and it's on a great transit corridor (easy access to NYC). It's main drawback is that the downtown area really lacks the same sense of place that Portland offers. It's about as generic a New England city as you'll find. However, there are those that write Stamford off as a New York suburb that just happens to be within New England's boundaries and they have a good argument (though I'd still argue that New Haven is very much a New England city). If Stamford doesn't count, Portland gets my #5 spot.

Hopefully someone with almost equal experience in all four can weigh in.
 
I'm actually surprised Freeport is the top visited town in Maine. I would have just assumed Portland or Bar Harbor (maybe even Camden or Ogunquit). But I guess Freeport's status as a hybrid town/ outlet mall would make it a year-round destination (I know buses go up from MA all year round) whereas Portland and Bar Harbor would see stronger fluctuations in visitors with the seasons.

Some people doubt the numbers, but I think if they are correct you are exactly right.
 
I'm actually surprised Freeport is the top visited town in Maine. I would have just assumed Portland or Bar Harbor (maybe even Camden or Ogunquit). But I guess Freeport's status as a hybrid town/ outlet mall would make it a year-round destination (I know buses go up from MA all year round) whereas Portland and Bar Harbor would see stronger fluctuations in visitors with the seasons.



I don't know if I'd go so far as to call those things anti-urban. Bellevue Avenue (where most of the mansions are centered) is not necessarily "urban" because the houses (estates, really) take up so much square footage and have well manicured lawns, etc. However, it's not anti-urban either. It's merely a few blocks from the city center, it's walkable (part of the draw of the mansions is that they're all spaced out in city blocks within walking distance from each other). Bellevue Ave. is a wealthy streetcar suburb on steroids in that you have single family homes within a typical urban grid that are all close to the core of the city. Not unlike the Western Promenade in Portland's West End or the houses along the Jamaicaway near Jamaica Pond in Boston. The caveat is that the homes in Newport are MUCH larger. Still, at worst it's suburban and it's the kind of suburban that we all appreciate in cities.

The Cliff Walk isn't urban because it's a natural feature, but given the proximity to downtown Newport, I'd say it's something akin to a great city park which is essentially urban. Public spaces are part of any city's urban appeal and the Cliff Walk is part of Newport's. I'd throw it in the same category as the Eastern and Western Promenade in Portland, Emerald Necklace in Boston (outside of Central Bosoton), or the Presidio in San Francisco. It's not a central urban park, but it's a great natural feature in an urban environment.

The Tennis Hall of Fame is easily the most urban of the bunch. It's a museum/arena cluster in an urban part of town. In fact, The exterior of the THoF is retail and dining space coming right up to the sidewalk (google maps). I don't see how it's any different from a place like Fenway Park except that it draws people in on a regular basis (because of the museum) instead of just sporting/concert events.

We're definitely on the same page re: Market Square in Portsmouth. I don't know if it's my favorite urban space in New England (I've always had a soft spot for North Square in Boston), but I'd say it's better than any one spot in Newport, Portland, or Burlington too. That said, I think you'd find similar urban vibrancy on Thames Street in downtown Newport and maybe even more so on Bannister's Wharf (easily one of my top 5 urban spots in New England). Still, The cohesiveness of downtown Portsmouth, in my mind, beats the others.

I'd also say that Spring Street (take a virtual stroll on google maps) and the intersecting streets remind me a lot of Portsmouth's Strawberry Bank and Washington Square and Trinity Park are as good as any central urban park anywhere.

Out of Portland, Portsmouth, Newport and Burlington, I'd say that Portland easily has the best restaurant scene of the bunch. I don't know which I'd give 2nd place to because I haven't dine in Burlington or Portsmouth enough to compare to NPT. For nightlife, it's got to be Newport for me. But again, I've only gone out extensively in Newport and Portland of that bunch (last time I went out in Portsmouth, you could smoke in bars). Newport has a great collection of bars downtown and just beyond(more than most cities 3x its size). Many of them are right on the water. One of my favorite Irish Pubs anywhere (Buskers) is in Newport. And while Newport's bar scene is clustered together so you can really walk to any of them, you get different atmospheres depending on which direction you go. Downtown bars are typically a little more "yuppy" (with some exceptions) while Lower Thames (South of Memorial blvd) has a more local scene. Broadway, just north of Washington Square has much more of that granola, artsy vibe. I'd also give the edge to Newport for shopping too since it has a large representation of both local and national brands. More so than the other three.

If we're talking simply attractive to tourists, I'd probably go like this:
1) Boston/Cambridge
2) Portland area (inc. Freeport, Cape Elizabeth, etc)
3) Newport
4) Burlington
5) Portsmouth

Now, if we're using this criteria "there has to be some combination of the urban dynamism that attracts tourists (not to mention students and retirees), along with employment centers, urban amenities, livable and walkable neighborhoods, and so on.", my list would be as follows:

1)Boston/Cambridge (easy)
2) Providence- enough merit to make it a great city on its own, but proximity to Boston is a huge bonus
3)New Haven- a lot of people discount CT, but New Haven is very much a New England that happens to be on major transit corridors- I-95, Amtrak, Metro North, I-91, etc.
4)Portsmouth- On its own, Portland would get the edge in my opinion. But Portsmouth has a lot going for it independently with the added bonus that it's a reasonable commute to Boston from Portsmouth.
5) I'd put Portland or Stamford here. Stamford has a lot of shopping/dining downtown, it's on the coast and it's on a great transit corridor (easy access to NYC). It's main drawback is that the downtown area really lacks the same sense of place that Portland offers. It's about as generic a New England city as you'll find. However, there are those that write Stamford off as a New York suburb that just happens to be within New England's boundaries and they have a good argument (though I'd still argue that New Haven is very much a New England city). If Stamford doesn't count, Portland gets my #5 spot.

Hopefully someone with almost equal experience in all four can weigh in.

I'd agree with your assessment of Market Square. However, I think Post Office and Tommy’s Park in the Old Port, and Monument Square, as well as Church Street in Burlington, come close. But you’re right, Market Square wins by more than a slight margin—it’s a wicked cool spot. Sometimes I wonder if it’s too cute for words, though, like a stage set (a la Exchange Street). This gets back to your point about liking a little bit of grit. I don’t know.

I would differ in the last list (urban dynamism). I think you’d get the first two right (1) Boston/Cambridge, (2) Providence, then I’m not sure. I don’t know a ton about New Haven, so maybe you’re right. But what I’ve heard is that it’s nothing compared to what it was, or what it could be. I’ve never heard anything good about it from anyone other than urban enthusiasts who look through rose colored glasses. That’s not to say what I’ve heard is necessarily accurate.

I think you’re right Portsmouth’s proximity to Boston gives it an edge in some respects, but then again that factor would only matter to people who value a larger city for its amenities. In that case, I think you get more out of Portland at only another 45 minute distance from the big city. In my opinion, this probably puts Portland—especially with its educational institutions and cheaper housing—ahead of Portsmouth.

This is all very subjective, so I think the only real way to rank a place’s comparative importance is by population. The numbers speak for themselves. But that gets tricky because of density and square mileage making it an apples to oranges comparison sometimes. Then, the metro area becomes a good proxy for population. I think comparing metro areas is the best way to do it. And not combined metro areas, just metro cores. I could be wrong.
 
Recently read somewhere that the Downtown Portland/Old Port is the most visited spot in Maine and it actually surpassed Freeport by a substantial sum. Will research the source.

Lrfox, the debate between Portsmouth and Newport when it comes down to tourism is such a tough call. They are really mirror images of each other due to similar populations, both are seaports, both have US Navy connections, and they both are extremely popular cities to visit and explore. I think downtown Newport is more quaint/charming and downtown Portsmouth is more commercial/urban in feel. I like them both equally but still have a problem sneaking either ahead of Burlington.
 
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Found a couple of articles that puts Portland at the top of the most popular/visited spots in Maine. One source actually had Bar Harbor ahead of Freeport, and another had Camden/Rockland at number 3. Portland's advantage as the state's transportation hub via air/train/bus/cruise ships and having Portland Headlight at the entrance to the harbor helps considerably. Don't forget about the shopping, museums, restaurants and very popular Old Port! I am sure that Old Orchard Beach sends a large number of visitors downtown during the summer months, they all can't fit in the Maine Mall during cloudy/rainy days.
 

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