I grew up in a small, small town in NC. Halloween was a fun time of year, the county fair had just ended, and the air was cool and crisp. We had a big yard so we were able to have several areas of decorations up at once. Our house was an old farmhouse, so it came with the pre-spooky feel already (yes, we did have at least one ghost in the attic, but it was friendly), so decorating inside was easy. I think what made it so special though was that my Mom and my Great Aunt were Halloween fanatics (they instilled it in me from an early age). I always secretly thought my Great Aunt must have been a witch because she lived alone in a big spooky house on a hill, and decorated with owl memorabilia for all seasons.
The drawbacks to small town Halloween were mainly that being such a small town, and we were further out in the country, that you never had many trick or treaters coming to the door. My Great Aunt lived closer to town, so we would go to her house and set up for Halloween there while she was alive, and we would get more visits that way. The other issue that you faced in the small town environment was a dearth of supplies. Aside from Walmart and Kmart, there weren't any major stores for decorations when I was a kid (There's more there now, but not much). To get really good decorations, we had to ride to SC (about an hour away) to go to the Spirit store and Michaels and other stores known for good decorations.
Now that I am an adult, I live in what I consider the big city, although I am nowhere close to the "city" itself. I live close to Disney World, Seaworld, and Universal. Busch Gardens is only an hour away. My wife and I enjoy going to the parks for their Halloween events each year. Our favorite is Disney's as it is more fun, and not gory like Universal's and BG's tend to be. Seaworld's is fun, but geared more for small children. We have a LOT of good places to shop for Halloween decorations, there are several Home Goods within easy driving distance, numerous other TJ Maxxes and Rosses, we have multiple Michaels stores, Targets, Spirits, and Hobby Lobby here, so it is easy to find good decorating (too easy). We also have a good many Trick or Treaters depending on the day of the week it falls. Last year was good, I don't know how this year will go on a Monday.
The drawbacks to City Halloween are that you mostly don't know everyone in your neighborhood, so there isn't that sense of community, neighbors and friends don't drop by to see our decorations like they did in NC. This next part isn't an issue everywhere, but here in FL, it is HOT for Halloween which takes away a little bit of that autumn feeling. There is no small-town fair to go to close by during the autumn season.
So it's a trade off. In some ways Halloween in the city is better, and in others I miss the small town feel we used to have. With that said, I wouldn't want to go back at this point for other reasons (job opportunities, pay, health, etc...), but I do look nostalgically back at those old small town Halloweens from my childhood and smile. I know that if my Great Aunt and my Mother were here today, they would still be doing Halloween the way I remember it, and that's why, no matter where I am, I try to do it the best I can, in their memory.