[Alfirin]

I don't think Smaug would want to completely destroy Esgaroth, just do enough damge to put the town in fear of him again. The town would be a useful source of tribute to him if not in gold than in food. A dragon as big as Smaugh would need a lot of food and Esgaroth's livestock (not to mention its citizens) would be like a cornucopia of low effort munchies (swoop down grab something and dinner is served; no hunting required)

As to the question of smaug's landing in Esagroth proper, I think it really depends on exactly what shape you think smaug is. If you think he is a stocky lizard shape then your right he can't if you think he is more sinous and flexible in from then he migh be able to coit around a rooftop. and if you belive (as I do) that flying dragons were closer to wyvrens in shape (i.e. that the wings were attached to the front legs not coming independenly out of the back) than smaug migh have landed in a more bipedal sitting, stance, in which case the space needed would be much less (say the size of the town square)

As to the comments on my earlier post I agree I had frogotten about boats however I'm not sure that there would have been sufficient boatage to get everyone off the island. most of the boats would proably have been small fishing vessels capable of holding five or six people tops. The vast majority would still have been stuck without the bridge. Moreover boats would not be as safe and exit as they sound at first. It takes time to set sails and rowing is slow. The hot air, both from Smaug and the burning city would probably have mucked up the wind assuming there was any that night. All the boat leaving at once would have ment serious problems with wakes bulding on each other into waves. Not to mention that anyone in a boat would be more or less a stiing duck should Smaug decide to fly over and spary them with flame. (or if he was really clever slap the water with his tail and make some serios waves. On that subject I'm not sure where everone is getting the idea that spraying water at Smaug would have been an effective weapon. Dragon fire (unlike say a campfire) is most likey self renew and probably cant be squetched by spraying liquid in the mouth (if it could than a dragons flame would go out every time it ate or drank. Water might have been good for putting out the fires Smaug made but any water sprayed at him while he was breathing flame would have probably just evaporated.