For about a year, weekend after weekend I remember dishing out at least $7 for parking downtown. There are those paid parking lots scattered throughout the downtown area, and plenty of them all looking for your $7, threatening that you'll get tickets from the Hartford Police Department. The thing is, they are ripoffs. The city has a great, very reasonably priced parking system already built in. You don't need to pay over priced vendors. All it takes is a little knowledge about the system.
I'm not saying they're good if there is absolutely no parking whatsoever, but chances are that most weekends, you won't need to pay for parking. Metered parking is free after 5:00pm, so if you're going out at night you don't have to worry about the meters. The majority of paid street parking actually are no meters. Most of have switched to these computerized machines that give you a parking receipt called "Pay and Display Meters". The good thing about these is that you can use a credit/Debit card on them, and pay for as much time as you would like.
Now, this may be a little old fashioned, but if you drive around for probably less than five or ten minutes, you will find a parking space for free. Downtown Hartford isn't necessarily the most happening place, and paid parking is something that can almost always be avoided. There are "no parking" signs all over the main roads, but they always say between certain hours. For example you can park directly on Main Street, and there are usually spots there, plus you will not have to pay a dime. If you're out on the town at night, chances are you CAN park in every spot on the street. So save yourself at least $7 a night, and buy yourself an extra drink. It will make the walk to the car a lot more enjoyable and you won't have paid for a small piece of pavement for the night.