I'm surprised it hasn't been said yet, but you might want to look into some self-wrenching, rather than a bike shop for this. Being it's your first road bike, and it's a *very* low end, department store bike, you will spend way much in labor (and parts) than you should. Bike shop labor is not cheap. They'd likely sell you a new bike before they worked on a Sears cycle.

A good place to start, to learn, is: https://www.sheldonbrown.com/ - any questions you can't figure out there can generally be answered by searching bikeforums (If you had a stuck stem for instance, go to Google, type in "stuck stem site:https://www.bikeforums.net"). If it can't be answered by searching that & Sheldon, posting on the forums is your next best bet.

Seriously though, a Free Spirit is not something you can 'afford' to take to a LBS to get worked on.

Ride is more a function of tire width and air pressure.

I know that it is highly unlikely, but everyone is assuming that this is a low end Free Spirit... Does this one happen to be the Ted Williams model with Reynolds 531?

Also, in my experience a cheap bike is likely to be heavy and perhaps sluggish, but they tend to absorb road shocks well. Of course, that is just my experience.

Could just be the fit. A properly fit road or mountain bike should not be messing with your DNA-to-be.
A saddle on a road bike is simply not a resting spot; it's designed to keep your hips over the pedals and the seat post from becoming more than a little friend....weight distribution is more equally spread to your arms, legs, and butt.

Reynolds101, the attraction of a road bike, especially to a former BMX-er, is speed. Pure and simple go-fast. Even touring bikes, at a liesurely pace, are moving pretty well. With that comes certain features of a road bike that are different than what you may be used to.

Simply put, the purpose of a suspension is not to comfort the rider; it's to keep the wheels in contact with the ground. A road bike tends to assume that the rider is avoiding road hazards. Road hazards, in the road bike world, include small rocks and pretty much any object or deviation in the road surface that can upset a 1" wide tire with lots of air pressure.

A Free Spirit, outside of a few rare models (acknowledgement to Darwin), is a sturdy, fairly heavy steel bike, generally with steel wheels, made to compete with equally heavy Schwinns of the era, at a lower price. With weight comes a measure of smoothness, and you can smooth it out a lot, but it's still a road bike, and a pretty basic one. Fun, but not the speed thriller you can easily get for decent prices today. Even the heavy Scwinns of that era, while lunkers, are pretty smooth.

Walmart is selling an aluminum road bike with 3x8 Sora for $400, by the way, which I have to admit is an excellent way to get into road biking with a minimum investment and shallow learning curve on the shifters, etc. Not that I'm advocating that. My opinion is that once you get a really nice road bike, you'll quickly learn to appreciate what it's like compared to the more entry-level bikes. It's often akin to the difference between AM and FM.

Based on what I've read, you may be better off selling that bike and searching for a better road bike, often called a "bike shop" bike, which means they were available only in bike shops. The used market is very reasonable, and you have a wide variety of options in shifters, frames, wheelsets, etc.

The John Deere of bicycle categories.

Well the general consensus here seems to be that this is just not a great bike, plain and simple. To Little Darwin, the model is Free Spirit FS10.

To RobbieTunes, you are correct. The aerodynamic style of a road bike is something that grabbed my attention seeing that I could go fast. But, its not the only factor that dictates what style of bike I would buy.

Now that I've done some thinking, I just may start riding to school on certain occasions. I drive a Ford Explorer, and its not the greatest on gas. Especially when I'm already a broke college student. The idea of commuting to school and to work sounds great to me. I would much rather put in a little exercise and leave 30 minutes early instead of paying $80 a week for gas, mainly because I live somewhat close to the places Im going to.

If I were to do this though I would need a bike that is easy and quick to maneuver over sidewalks, bumps and other obstacles (such as a mountain bike), but still being able to maintain some speed to get to school/work quickly. All this for under $300, new or used. Am I asking too much here? If not could you guys give me a few suggestions? Im not looking for all the bells and whistles, just something that could get me from A to B quickly and safely, and something that I can ride around the bike path with.

Thanks for everyone's contribution so far too, really helpful tips and information.

My old SOMA Hi-Ten 10spd is one of the cushiest bikes I own.....

"The more you ride, the less your a-s-s hurts."

Or something like that. "Comfort" is a relative term; I ride a road bike for almost everything and am fine with it. Other riders wouldn't like that sort of ride, and might opt for some other bike.

But here's my point: At some point the rider must adapt to the machine.
This is all the more relevant when the bicycle choice is made for you, for example, when you are riding whatever bike you have on hand. Advice to go buy a fitted bike and spend big $$ on a "shop bike" is alright as far as it goes, but it may not be in the budget for everyone. Nor may it be necessary in the beginning.

It sounds like the OP has the right idea - take the bike to a shop and have it combed out. Not everyone wants to do the wrenching, especially in the beginning. As you go along, you can learn the necessities.
Get the shop-ites to replace what needs replacing, upgrade as far as is practical and tuner 'er up.

Then get out and get some callouses on your butt. Aim for a 100 miles per week... then maybe look at getting another ride.

For cheaper bikes like the Free Spirit it'll be pretty normal. Lower cost steels are not as strong as the higher tech materials (Free Spirit materials science dates back perhaps 100 years, and that of 531 "only" perhaps 60 years, much stronger and hence lighter steels came available in the last 15 or so years), so they have to be thicker for the same strength. The thicker tube makes a much stiffer tube, hence more harshness over bumps. Modern steel frames have a supple feel that tends to reduce teh shock you feel.

A lot of riders put a shock-absorbing (pogo-stick) seatpost on to add to available saddle cushioning.

LOL, I don't care what bike it is or isn't ? A road bike is never going to be a cushy ride, not unless it's freshly paved asphalt. And on that, anything rides smooth.

First, understand that aerodynamics don't really enter into the picture until you start trying to go, say, 15mph or more or into a strong wind. Strong riders can go plenty fast, especially for short distances, on an upright bike.

Riding to school - good idea! It's cheap, convenient, and good for you and the environment. However if you need to leave the bike unattended be concerned about theft.

Finally, a commuter or hybrid bike will handle bumps better than a typical road bike largely because of the fatter tires. I would imagine you can find something good used for much less than $300, though location may be a factor. However riding over sidewalks is not good. People, especially kids, do it, but a bike does not belong on a sidewalk in most places. Riding over curbs, either up or down, will put a lot of stress on the wheels anyway. Just about any bike will do for a designated bike path, usually referred to here as MUP, Multiple Use Path, because despite a name that says "bikeway" many people walk or rollerblade on them.

I will reiterate, knowing nothing about the OP, there are techniques for riding that will smooth out the bumps for you. Get out of the saddle and keep your knees bent. It's like skiing.

If you want to plant your butt and never get up, get a full suspension off-road bike and put some slicks on it. They are PLUSH!

I put a suspension seat post on my 82 Fuji Ablsolute 10spd. just because I need to be in the saddle more, REALLY BAD KNEES) . It really helps me, but i agree with some of the other posters, sell it and cruise craigslist for a hybrid or commuter.

+1 and the harder you ride the less your ass hurts. If I just toodle around @ 8mph on my road bike I get all sorts of achy. It's terrible. If I put the hammer down everything's fine and dandy, though.

Big cushy seats are terrible. They usually just transfer the pain to just below your butt if you put a few miles on one.

Sore butt can sometimes be relieved from not sitting so upright. Bigger frames and longer stems can sometimes help in that regard.

+1 on Mike Mills techniques for smooth ride. Pedal hard and kinda float over the saddle. Keep your elbows bent. Pretend you're a jockey @ Churchill Downs.

Oh, and as to your worry about bike getting squirrelly especially at speed, many bikes get more stable the faster you go at least up to 25 mph.

The FS10 is not a bad entry bike and when you compare it to a new xmart bike it is considerably better.

It has a sport class wheel base and more relaxed frame angles and with some nice tyres and a good saddle the high ten frame should offer a pleasing ride.

If one has not ridden a road bike to any degree it will feel harsher than a mountain bike but if you have ever ridden one of those bike shaped aluminium objects from x mart you will know what stiff and bumpy is all about as they have a horrid ride quality.

Have turned a number of FS10 models into economical FS1.0 models and in riding them would say they are not bad... a really strong rider might find them to be a little flexy and whippy under high loads but for a casual rider this translates into a frame that does a lot to take the buzz out of the road.

With a road bike technique is really important and you should not be taking up all the bumps with your ass... this is what your arms and legs are for and this applies to every type of bicycle..

"Big cushy seats are terrible. They usually just transfer the pain to just below your butt if you put a few miles on one."

I couldn't agree more. When non-cyclists see the narrow carbon fibre "Selle Italia Kit Carbonio" saddle on my Vitus road bike they don't believe me when I tell them it's one of the more comfortable saddles I've ever used (picture below). A road bike saddle is not to 'sit' on in the same way as say a car seat or motorcycle saddle which generally are the more comfortable the thicker, wider and more deeply cushioned they are. A road bike saddle supports the two "sit bones" (I can't remember the proper medical name for them but they are the two bony points at the bottom of the pelvis between the legs). Your legs must be free to pedal without rubbing and chafing on the sides of a thick saddle and thick padding on the top just means that your fleshy parts will be rubbing against it all the time, causing more soreness. as others have said, tyres are an important choice and improving your position on the bike by adjusting saddle height, angle and fore/aft position plus handlebar height and angle is equally important to comfort. The aim is to spread your body weight between the three contact points: seat, hands and feet. If any one carries too much of your weight the ride will be downright painful. Also as others have pointed out, bumps, kerbs and potholes are to be avoided and not ridden over. That's just common sense - they impart impact shocks to you and the bike so can damage the bike and cause you pain from bruising. Even though your Free Spirit sounds as though it's on the lower levels of the range, provided that the frame is the correct size for you it should still be possible to adjust it to give you a smooth and comfortable - though possibly heavy - ride. Then you can start to enjoy it, save money on fuel and cut your personal carbon emissions!

They are your ischial tuberosities.

Some good advice in the last half dozen posts! Based on my own experience, I would not recommend a suspension seat post, so it's interesting to hear them recommended.

Reynolds, you can certainly make that Free Spirit ride pretty well and give you a pretty good idea what riding an old road bike is like. It will be bumpy if you just sit there, but if you put your butt in gear and actually ride the thing like a sports car, you'll forget all about the bumps.

A better bike would probably be better, I can't deny that, but this one is probably fine for now. I vote, keep it and ride it and learn to maintaiin it yourself. Learn enough about this one that when something good turns up on Craigslist you know enough to grab it before its gone.

I'd get a B-72 Brooks instead of a suspension seatpost. Comfy! And you could move it to another, nicer bike later. Just keep the old seat so you can put it back on when you sell it.

To help control your bike on cobble stone, rocks or other genuinely gnary surfaces like the streets of New York , when you get out of the saddle, squeeze the sides of the saddle with your inner thighs. This will help prevent the bike from jumping around underneath you when you are out of the saddle.

Yes road bikes are bumpy because they have no suspention. All you have are the tireds and seat for comfort.

Saddle time adds alot of mojo. Dont forget the engine. And the tire psi does make the difference at certain times (but not so low you risk pinch flats).

drummerboy is right and his comments suggest that real comfort is possible. From this many people assume that by adding squishy, under-inflated tires and a large, soft gel seat you will get a plush ride. Sorry, I have to disagree.

Now, pain and utter discomfort shouldn't be a part of the road bike experience, but there are several things working against the idea of lush comfort on a road bike.

1. Frame geometry
The angles of the various frame tubes are tight, much closer to vertical than on other bikes. Think of the differences between a beach cruiser and a road bike and you'll see what I mean. Because of this, most of the shock, vibration and bounce from the road is directed straight upwards.
2. Tires
Road bikes invariably run small, high pressure tires. So you have a razor-like, high pressure tire with a correspondingly small contact surface on the road. Its like riding on an o-ring! Now this is great for speed, because such tires offer little rolling resistance. But if you decrease the pressure to "soften things up," you risk pinch flats and poor handling.
3. Rider Position
This is a function of frame geometry, really. Because of the tight frame angles, you are forced into a kind of hunched position. This requires both a certain suppleness and strength in the muscles. When you are unaccustomed to this positioning, every little bump and jolt is noticed.

Good fit can alleviate the problems that come with these factors, fortunately. Keep in mind the purpose of a road bike - speed. You are in contact with any bike in only three places: butt, feet and hands. If you are right sized to the road bike, then your torso and legs stretch out and you are not cramped. This keeps you low and aerodynamic. It is also an efficient position for transferring power to the pedals. The seat is the last point to be considered.

Due to the balance established by the three contact points, you don't really sit on a road bike seat... you balance on it.
I think of it as a pivot. Instead of sitting, you really "perch" on the ischial protruberences, what people call the "sit bones."

This means the seat has to properly support those particular points of your anatomy, about 3 square inches per side. Meanwhile, each person has a different placement of these bones. Mine are wide, yours might be narrow. So, your skinny little seat wouldn't offer me the same support you get. Yep, seats have to be sized right, too.

More good new: when all three contact points are in balance through sizing of both frame and seat, things get better. You'll find that you can let let go of the handlebars slightly and not feel like you are falling forward. Neither will you automatically try to spring upward. You'll feel yourself balancing there, well... like on a centered pivot.
From there you can float and your own body acts as a shock absorber. This is really where the road rider gets his so-called "comfort."

It still can be tough in the beginning if you aren't used to it. That's when YOU adapt and push through the minor discomfort that comes with the road bike.

rhm.
Please note, I did not recommended he use susp. seat post, I said I use one. Do they belong on a road bike? Probably not. On my Fuji anyway, it sqeaks and squirms and some times, on a really bad stretch of road I frequent, I wonder if it has turned in the seat tube. I also have a nice older Selle Royal leather saddle on top the pogo post. NEVER A GEL SEAT. I need to sit where most riders would just be a hair off the saddle, to save my knees for the streches where I do need to be out of the saddle.
Proper overall fit ,as mentioned all over BF, is a must, so OP should maybe get a proper fitting.
Or, just go get a comfort bike.

lift your ass up when you're going over bumps.