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I've been carefully reading through the outstanding Erebor supplement, and one thing has struck me both times that I have read over the descriptions about the city of Dale:

They've got this impressive Gate that surrounds most of the city. It says on p. 39 that "Anyone wishing to pass into or out of the city unnoticed must, in general, go over the wall."

But the Map (on p. 37) shows that the Gate doesn't seem to circle the entire city. There's a huge opening for the docks and quays in the South-Eastern section. It seems that people that want to enter the city via a boat would have a pretty easy time of things. It even tells on p. 39 how the officials have a hard time (during the day) keeping an eye on all that is going on, with all of the hustle and bustle around them. One could surmise that things would be even easier at night, especially for persons who were stealthy.

Has anybody else considered this? It just seems a strange matter of security for such a wealthy and prosperous city, that otherwise goes to such trouble to keep people from easily entering, to have this huge open area where anybody could pretty easily get in...

That's kind of natural for a city with any kind of port. You can't really wall up your port if you want to use it.

Not sure about that Jussi. Would most historical river ports not have had the docks outside the fortified area? Also, wouldn’t sea ports have had a sea wall and the ability to raise a boom to prevent the entrance of hostile vessels?

...and that's why Dale has the only Thieve's Guild of all Middle-earth!

Also, while we look at a cities defenses from an "adventurer's" point of view (the first thing we think is about plunder, stealing and storming the city), the vast majority of people that come to a town aren't masses of thieves and smugglers. Thus, usually it should be enough for a pair of guards and a taxman to board each boat or ship that docks in the harbour and write down the name of the captain, their cargo, and how long are they planning to stay. Then they collect the taxes and that's all the work there is.

And yes, once in a while a thieve or a smuggler gets by. Then it's the city guard's duty to catch him.

Also, Dale was built in the summit of peaceful and joyous times: a good addition as the area darkens would be to build a wall between the docks and the city to protect the citizens in case of an attack. The walls would have guarded gates as the rest of the entries to Dale.

Unfamiliar boats that try to enter will probably be noticed. Everyone has a place they dock. A stranger will probably make a mistake and do something unusual...
So you need to use a local boat, follow the rutines, although seemingly chaotic at first glance.
The same kind of preparation is required to Enter through the gate undetected.

Another thing worth of considering is that, in pre-modern times, a lot of security wasn't exclusively handled by the "city guards" (when those existed).
Common citizen handled most of the security by themselves: foreigners stick like a sore thumb in a city of, say, 5'000 peoples, and most citizens would intervene immediately as soon a fellow citizen is asking for help ("hue and cry" and so on).
That means that if you are a well liked citizen you can get away with behaviours that would otherwise be deemed suspect. Conversely, a foreigner would be eyed, questioned or even confronted for any unusual behaviour.

A few thoughts to add to the comments above. Ignoring infiltration by very small numbers of "enemies" (spies and mischief makers) which would be easy via the gates in the wall or the harbour (as it would be in any town or city), any major attack via the harbour would require boats - lots of boats. Now I may be wrong, but Dale's main enemies would be orcs and Easterlings. Orcs are hardly known for their boat-building and Easterlings even less so (apart perhaps from those living around the Sea of Rhun). To build boats you'd need wood - and the elves might have something to say about that. To bring boats (from the sea of Rhun for example), you'd have to either (1) carry them across the upper marches (no small task) or sail them up the river - BUT you then have to get them up the waterfalls at the long lake - which would allow for a perfect counterattack and the burning of boats. In all honesty, given the logistics, you'd be better to bring siege towers and storm the walls - almost certainly involving less "kit" to manhandle across country. Then there's the two tall towers at the ends of the walls which probably have dwarven war-engines (ballistas, catapults, etc) capable of launching flamable projectiles. I suspect a river crossing would be a tough call and how many orcs or Easterlings can swim?

In my own campaign, shortly after Sauron announces himself in Mordor, the Bard requests Dain to construct a cataract on the river above Dale to allow for a flood of the river in the event of an attack. He also commissions the dwarves to construct a great chain and capstan which can be raised on the river to close travel upriver beyond the southernmost river tower on the walls.

Anyway, hope that's useful

In the last years of the Third Age is anyone keeping watch on the portage-way at the south end of Long Lake? If it is unguarded then enemies could port boats up from the Running with little trouble, especially if soldiers were sent ahead to secure the upper portage.

As Corvo points out, foreign agents might stick out. However, that is all the more reason to recruit spies and other agents from among the citizens of Esgaroth. There would be plenty of places both in town and out where a foreigner could meet with a private citizen, especially if the local was a merchant or trader.