Need bike info
The components used on the department store bike are going to be older technology or less durable. Two years ago I wouldn't have thought this was a big deal, but I've put 6000 miles on my bike since then and it definitely makes a difference. Shimano 105 components are a good option, and if you can find a mix of 105 shifters and Ultegra derailleurs, go for that.
The frame materials on a lower end bike are most likely going to be heavier, making your bike a little bit slower.
It's also a good idea (but certainly not necessary) to get a good relationship going with your local bike shop. If you're going to be riding a lot, you will probably be needing a bit of service on your bike and maybe will be wanting some extras like aerobars or clipless pedals. Wal-Mart can't do that for you. Now is also a great time to find sale bikes, since they are probably looking to clear out some inventory.
Some options for you in the $800-$1000 range off the top of my head:
Trek 1000 or maybe you can find a 1500 on sale
Specialized Allez
And Giant makes some in the 800-1000 range, perhaps they are called TCR? I am not sure on this one.
Definitely a huge difference in quality by going to your bike shop. I would compare going to a bike shop as though you were going to a reputable car dealership when car shopping. Going to Wal-Mart is like looking for your new car in a junk yard.
Okay, maybe not that extreme, but in some cases that's not far off. Proper fit is important, and I'd rather rely on my bike shop's knowledge and not Wal-Mart's. There's a time to save money and a time to pay for quality, don't skimp if at all possible ($300 should be able to get you a great bike, $1000 would be an awesome bike).
Just be sure to get as nice of components as you can (decent derailuers, pedals, seat etc). There's no point in buying a good named brand (Trek, Specialized, Bianchi among others) if you're going to get crappy components on the bike that will need replaced.
http://www.calorie-count.com/forums/post/3578 2.html
my post #9 in that thread gives some concrete examples of reasons not to buy from a chain store. but if you are savvy on safe bike inspections and can spot problems (like badly run cables or the wrong length chain) when you look over a prospective bike, and you don't care about establishing a relationship with a shop & a mechanic (something i consider a smart thing to do) then you could find a cheap bike.
Also, a bike shop is going to stand behind what they sell. If something breaks, they'll get it fixed. Walmart might take the bike back if it's new enough, but if it's been a few months and something goes wrong, you'll probably be screwed.
If you really want to get serious, then go to a bike shop. You will not regret it.
Edited to add: When I started cycling, I had a Walmart bike, a cruiser. Nothing wrong with it for casual riding, and it was only $99.00. But when I realized that I really wanted to get out on the open road, I knew that the cruiser wasn't going to cut it. I stopped into a bike shop "just to look around," and came home with a new Trek hybrid and $600 poorer. I thought I was nuts...for about a day, until my first ride out on the road. Haven't regretted one penny of that purchase ever since. :)
I was in the same shape a few years back - I had an older bike, but really wanted to update to some of the nicer features bikes have now, like index shifting and brakes that actually stop
. I wasn't clear from what you posted what type of bike you were looking for, but two things that I did see that hadn't been mentioned before:
1. Be sure to give the pure road bikes a fair shake prior to writing them off for the bigger seat or the fatter tires of a mountain bike or a cruiser (unless you really will, indeed, be riding down mountains). As a couple of folks mentioned, weight is a huge factor, and if you don't need full suspension and knobby tires, that'll be just like dragging an anchor around. Also keep in mind that a soft, padded seat is comfy for watching TV, but a firm seat that minimizes chafing and fits your "sit" bones right is what you want for riding a bike.
2. In terms of brands, I had a similar budget to what you mentioned. I finally settled on a Jamis Quest. It's a wonderful ride - nice steel frame, terrific components, good weight, and has been ultra-durable. I'm coming up on 5000 miles on mine. Not all the big shops stock them, but there's usually a dealer in your area. I also liked the Giant TCR2, but it was a little racy in profile for me, and the Trek is a completely safe choice (decided to stick with the mellow steel feel instead of the aluminum they were offered in at that time).
Good luck!
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