Winterhaven is the hub town for Keep on the Shadowfell, and it's one of the most fundamentally flawed pieces of design in the module. Why flawed? Because it favours buildings over characters.
The map above comes with the module. Each building is drawn on the map, and numbered. A corresponding three-page section of the module describes each numbered building, and then describes the NPCs that might be encountered at that location.
It's problematic for a number of reasons. First, the seventeen buildings shown don't seem enough for Winterhaven's specified population of 997. They could hold maybe 150, with the remaining 847 presumably living in the "small thatched homes [that] stand around Winterhaven, each fronting a piece of farmland or pasture". Even at a fairly generous person-t0-farm ratio there have to be over a hundred of these dwellings outside the town walls, none of which, of course, are depicted, described or referred to.
But that's a minor gripe, as is the second problem, which is that the design is prescriptive. The included map doesn't leave any room for the DM to add more buildings to suit his players and their play styles. Naturally he can throw the map out the window, but that brings us back to the question of what, exactly, he's paying for.
The main problem with building-first design is that it's unnecessary. There aren't any time-critical encounters set in Winterhaven. The players are never going to have a problem navigating an area this small. They aren't going to need to know which buildings are close together and far apart.
The building-first design comes with a significant cost - the NPCs. Anyone who's read an expansion for World of Darkness or 7th Sea knows what good NPC design looks like. In good NPC design, the DM is provided with descriptions, mannerisms, fears, hopes, desires, competencies, and plot hooks for each and every NPC that turns up. It's often more than the DM needs, but that wealth of detail is, again, what you're paying for.
The NPCs in Winterhaven - who are practically the only friendly characters in the module - weigh in at four sentences each, focused mainly on what on what they know about the local area and what they have to sell. Some insulting DM advice on page 32 encourages you to fill in the detail yourself by adding "an accent or favourite saying" or "[applying] a personality-related adjective to your NPC", before finishing with the suggestion"Make up your own stories".
It's a shame Wizards of the Coast didn't release this as an online sample of Keep on the Shadowfell. Revolutionary advice like "make up your own stories" could have saved everyone the cost of a pre-packaged adventure.
 The description of Winterhaven emphasises that it has a barracks, a warrior's guild, defended walls, and a cache of siege supplies. However in Keep on the Shadowfell Winterhaven is never directly threatened. Was a planned siege of Winterhaven cut for space reasons?
 The module mentions that mounts and potions of healing are sometimes available in town shops. Why, from a gameplay perspective, is it only sometimes?
 Winterhaven includes a Warrior's Guild. The guildmaster is the same NPC who runs the Winterhaven Barracks. What purpose is the Warrior's Guild intended to serve above and beyond the Barracks?
 Despite the area around Winterhaven being "menaced by kobolds", Winterhaven apparently has a market square and a Market Day. After giving a meaty description of this event, the module goes on to note that any given item from the Player's Handbook only has a 50% chance of being available, and armour, weapons, implements or magic items are "almost never" present. There is also an NPC involved who has no noteworthy mannerisms or quest hooks. How and why were the PCs intended to interact with the market square?