I own several sites I'm building up into a decent portal for my local town, and then the goal will be to expand outwards to other towns, so my needs are different from many webmasters in that I need to promote my site online and offline. Are there any other local site owners or travel site owners here who'd like to talk about promoting a travel/local portal?

Let me start the ball rolling; I have a couple of people working with me, and in the future I'm going to bring investors into the business. At present income comes from advertising (AdSense and local business), teaching English, and consulting fees. In the future I plan to add affiliate programs if they are specific to my site readers.

However, I'm struggling to promote the site offline. Sure, everyone who is important in town knows me, but they aren't my target market. Spending money on local advertising isn't an option, it's too expensive, so I'm relying on word of mouth and emails, but very soon I'll be printing t-shirts for staff and fans to wear, and flyers for car windscreens.

What are you doing to promote your travel/local portal?