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You might want to poke around the beginners forum-- this one is usually infested with sharks.

You really don't have much of a budget for a new road bike. I don't think any new Trek's are in your budget--- actually no new road bike worth buying can be had at your price (avoid the GMC, and other crap on ebay-- and avoid any dept. store bikes).

The other issue is that Trek authorizes no internet sales of their bikes. Most reputable makers don't allow internet sales (Giant, Specialized, Cannondale, etc.). European brands are often available online, but they are out of your range. There are some mail order brands- but shipping will take a huge percent of your budget.

I recommend hanging out at your bike shop to figure out what size bike you need. Find out the dimensions- especially the top tube length. Then, if you live in a city, check out your local craigslist for something used and pick it up locally. Or you could even post a "wanted to buy" ad. The alternative is to at at least double your budget. I would avoid ebay at your price range. Shipping would take up a huge percentage of the total cost.
 

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Well, there are the Trek hybrids, such as the 7000 for $270, which is a basic upright bike with low end equipment, or the 7.2FX, another upright with nicer, but still low end equipment. These both have fixed forks rather than shock absorbers, so they are more suited to road use. If you just want to ride around your neighborhood, there is nothing wrong with these bikes. I bought my daughter a 7000, and it is all she will ever need, since she will never be overly interested in riding.

If you want a Trek with drop bars, the cheapest is the 1000 at $710. It comes with a Shimano Tiagra rear derailleur, which is a step up from Shimano Sora, but below what most people on this forum would consider as the minimum for their bikes, which would be Shimano 105. Filtersweep is right, figure out what size bike you need, and check out used bikes, if you want a true road bike.
 

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I'd suggest you check the classified ads in the local paper and freebie sheets. Also, check the bulletin boards at bike shops, sporting goods stores. Even ask at the stores if they know of any available bikes. Good luck.
 
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