The town I grew up in was so small when you plugged in an electric razor the streetlights dimmed.
Okay, so actually I grew up on a farm. The nearest town was about 400. I’d put the cutoff somewhere around 2000.
Somehow I thought the Center Of The Universe would be more advanced than that. Flying cars and dilating doors.
My early childhood was three miles from a village of 1500.
Later childhood was on the outskirts of a village of 200.
Now I live in a village of 1200.
In Ohio, they aren’t big enough to be towns.
The weird thing? The village of 200 is the only one with a stoplight. 
Ah, but you see, my *home town * is 3000 miles away from here.
Also, I am “~ Center of the Universe” - approximately Center of the Universe - I live in Ballard, which is next to Fremont, which is, indeed, the established “Center of the Universe”.
There are more stoplights here in Seattle. And why yes, it is distracting and confusing! Oooooh, pretty colours…
Bear in mind, though, that in Ohio there is no such legal thing as a town. At population 5,000 you graduate to become a city.
To answer the question of this thread (and more), here is my general scale of classification. In all cases I consider metropolitan population, not city proper population, although most smaller places have no metropolitan area to speak of. So Boston, for instance, is a “big city” beacuse of a metropolitan population of 5 million, not a “large small city” because of the population of the city proper.
Small town: <15,000
Regular-szied town: 15,000-50,000
Big town: 50,000-75,000
Small small city: 75,000-200,000
Medium small city: 200,000-500,000
Large small city: 500,000-1,000,000
Small big city: 1,000,000-2,000,000
Medium big city: 2,000,000-4,000,000
Big city: 4,000,000-10,000,000
Really big city: >10,000,000
Probably too complex, but that’s the way it is. 
Initially, I was going to argue about this one - but googled around first, turning up these figure. Going on the 10m marker, the US has only two ‘really big’ cities (NY and LA), and Europe has none. Which I think is fair, when you remember the comparison is against huge and growing people-magnets in India, Africa and so on.
Aha! Then we are in dire need of definitions to make the distinction between towns, cities, villages, and other names for municipalities.
As N9IWP pointed out, in Wisconsin, a “town” is a sub-county geographical area, whose boundaries were made without regard to population totals or density. Typically, clusters of houses and/or businesses and/or industries break away from the town and form a separate government, becoming a “village” or “city.” And definitions of these terms differ from state to state, and country to country, I’m sure.
The largest municipality (that covers all types, doesn’t it?) in my county has just under 10,000 residents (the entire county has about 28,000). I would call it a small town (even tho it is incorporated as a “city”). But there are other munis near me with pops of 200 or so, and I would call them even smaller towns (even tho if they are incorporated, they are officially “villages”.)
My def of a small town is where everybody knows your business and you know theirs. Intimately. Make one misstep and you can’t hide. Everyone knows who the miscreants are by reading the police blotter.
Where the grapevine carries up-to-the-minute news, but the newspaper comes out once a week and by then, it’s old news anyway. Besides, everyone knows the reporter missed most of the real story.
Where the paper struggles to connect local people with international stories even if there are few logical connections (real headline this week: “Sturgeon Bay Native Survived Katrina”).
It’s a small town when the local newspaper’s front page headline is “Beloved local pet dies in his sleep.” When the letters to the editor are the first thing you read; you recognize the name of every person whose letter was printed; and at next church you tell them personally what you thought of it.
Or a place where, if you accidentally leave your wallet at the library and it is returned anonymously with all the cash, credit cards and keys intact.
Where, if you call in to the local radio station, the person who answers is the same person who takes the ads and requests for help to find the lost kitten, and who puts you on hold to go back on the air and announce the latest weather because there’s only one person running the station. Where call-in shows do not use a 7-second delay because there never has been a need. If you call in to a talk show and don’t give your name you still can’t be anonymous since everyone knows you by the sound of your voice anyway.
As you can see, these defs of a small town are more a state of mind than a rigid population number.
Doh! I didn’t know that.
Er, I still live in a village, though.
And our newspapers are filled with meth lab busts, so it’s not Rockwellian at all.
Our house is in a village, pop. 2200, that is within a town of 17,000. The whole area has a small town feel in my book, even looking at the larger town a lot of it is rural, and people live reasonably far apart from each other. The center of town is more or less an intersection. Within the town, there are a few hamlets, and between the hamlets is a lot of undeveloped land. When you are driving around town, you will pass houses, not on farms, just houses on largish lots next to other largish lots, and see kids riding a pony around the back yard.
In contrast, my mom lives in another village, pop 5500, and it feels a lot more “medium”, because everything is close together, it blends right in to neighboring medium towns, the center is bustling, and has posh boutiques. My village, on the other hand, has live bait. If you tried to keep a pony in your backyard in my mom’s village, the neighbors would be out with nine irons to set you straight.
My mom’s village and my village are only an hour away from each other, for what it’s worth. They are both about 1/2 hour away, in different directions, from Buffalo. Over the years, my mom’s village has become a real suburb, it feels like part of a metroplex (as if Erie County would ever be forward-thinking enough to organize itself on more of a metroplex model, but that’s a rant for a different day), while my village is, well, where they have live bait and the “no shirt, no shoes, no service” rule isn’t enforced.
So for me, it’s not just size, there’s also a “feel” that is hard to quantify.
The Detroit metro area is weird. Technically we’re all separate cities, but we’re crammed right next to each other. My Colombian friend (from Bogota) was weirded out that we specified that each area was a different city; to him, the entire metro area was Detroit and the suburban cities are more like big neighborhoods.
It makes sense to me, since my city is surrounded by others and the boundaries are rather arbitrary. There’s no empty spaces between cities; you just cross a busy intersection and bam! new city.
The entire metro area is about 5 million, I think? I’m used to being in a spread out, but highly populated urban/suburban area.
Small town to me is less than 15,000. Less than 10,000 is a really small town. Under 1,000 is where I’d go insane living for more than three days. 
There’s two cases of this in Britain - both the City of London and the City of Westminster are administrative areas within Greater London, and likewise the City of Manchester and City of Salford within Greater Manchester.
3.7m, according to the page I linked to earlier.
The U.S. Census Bureau says about 5.5 million for the Detroit metropolitan area, which is a county-based measurement containing a lot of outlying areas which one would probably not normally consider part of the “city”. The 3.7 million figure is one of those “urban agglomeration” numbers used in worldwide lists like that. The comparable Census number is the “urbanized area”; Detroit’s has a population of about 3.9 million. One could also make an argument for adding Windsor, Ontario to Detroit’s numbers, but of course the U.S. Census Bureau doesn’t collect information on Canada.
I think the Urbanized Area is the best way to define a city’s size, as it considers only the area of contiguous urban settlement and not a lot of rural land and totally separate towns, as the MSA (Metropolitan Statistical Area) does. However, the MSA population is most frequently cited by people and the media, it seems. Actually, metropolitan populations are most often ignored in favor of populations within city boundaries, which can really be misleading for purposes of comparison due to huge variations in city land areas. In Ohio, for instance: no matter what every single list and “state facts” web page says, I will not call Columbus the largest city in the state! It is still the third largest, and no one can change my mind about that!
I’d better stop now before I hijack this all the way to Cuba.
Any town with fewer people living in it than students attending my old high school. (4000)
[short continuing hijack]
I agree with you. I’m always amused by the people who live, say, 35 miles away from the edge of Detroit proper, with it starting to be the boonies* and they say they live in Metro Detroit.
Me, I live about one mile from Detroit, and the gym I go to is on 8 Mile.
- Not farmland proper, necessarily, but big open spaces, more plain 2 lane roads, etc.
[/ short continuing hijack]
A small town, to me, is anything under 5,000. It seems like a lot at first, but I grew up in a town of 4,000, and it was small. One stoplight, no large chain stores, no fast food places (that’s still true, BTW.) My highschool had ~500 students, and that was from my town, plus four other, smaller, towns.
I consider the town I grew up in in central NJ a small, farm town.
42 square miles with a population of 25,000 or so, 40 miles away from NYC.
The town I lived in as an adult in central NJ was to me, a small town, but a small, ‘urban’ town, since it actually had a real little ‘downtown’ area and a Main St., unlike the farm town I grew up in.
3 square miles and a population of roughly 16,000, 30 miles away from NYC.
The town I lived in for 4 years in PA was a tiny town to me - 2 square miles, population of less than 3000, 20 miles away from the college town of State College, PA, which to me, was also a small town.
Where I live now, I consider a medium-sized city.
40 square miles, population is close to 170,000. It is the county seat, and 50 miles away from San Francisco.
Same with the Chicagoland area. Chicago runs into Evanston which runs into Skokie which runs into Niles which runs into Villa Park which runs into Des Plaines - where there be dragons.
(I think. I’ve only lived on the North Side for a few years, so I’m kinda geography impaired.)
And it’s the same on the Western and Southern ends as well. So there’s a huge sprawl of folks not really separated by anything other than area codes and snobbery. When people ask me where I’m from and they’re not from around here, I’ll usually answer “Chicago”, even though Evanston is a big city in it’s own right - population wise. After all, no one could really tell the boundary between Rogers Park (neighborhood of Chicago, not its own city) and southern Evanston without a labelled map - one side of Howard Street is Chicago, the other side is Evanston!
I agree with Musicat’s philisophical definition of a small town. Anywhere you know every clerk you see in a day of errands by name, and half of them are cousins of yours, it’s a small town.
I think the standard is different out here in the Rocky Mountain West - I gre up in a small town in Wyoming - population 13. Considering that the biggest city in my state is only 53,000, small town is a whole different thing out here. I know people from Lone Tree, Wyoming - Pop. 3, and Cora - pop. 4 (in the 80’s, tourist have invaded and is likely larger now).
I grew up in a small town right on the Louisiana - Texas border with a Pop. 1200. It was certainly a small town. However, I now live in one of Boston’s outer suburbs. It is a picture perfect New England town with small town center, minimum land requirement for homes, and no chain businesses. It has a population of 13,000 and it still really feels like a small town. My parents, who have lived in many small towns, guessed that it only had 2000 people. Protectionist bedroom communities can really throw you off.