The question is
"Do you think I'll be able to hang with the group?"

FYI, I'm new to cycling and I may sound completely like an idiot.

I've been wanting to do a group ride, so I found a casual group ride, where the group was a loose pack of about 6~8 people keeping a line about a wheel length apart, cruising at about 18~20 mph going about 20~25 miles.
Personally, the ride felt more like a easy cruising and I have to do another 20 miles alone after the group ride to feel that I've worked out.
With that, I've been wanting to find a group ride that is more challenging, however, anything beyond the group I mentioned above are 35+ miles at 22+mph.
I'm not sure if I can hang with the group if I signed up for the group ride.
Yes, I understand the best thing is to try it out but the group is a bit away from me and I don't want to drive out there only to get dropped and lost in strange places. So hoping to cover my rear before I go out there; and get dropped and lost in strange places.

Some of the considerations are,
- I, for the most part, ride solo 3~4 times a week (30 miles @ 17~18 mph)
- During the ride I don't stop for rest but there is a mile or so of stretch (each way) where I have no choice but to slow down due to traffic where I consider it to be my rest
- Though there really isn't any climbs to mention of, the trail I ride is rather windy. Depending on the weather but it's usually about 10 mph, give or take 3 mph.
- Windy about half of the ride since its pretty directional but then again, its probably pushing me the other half of the ride.
- I'm completely unaware of the "more challenging group"'s route on a bike, however, I would assume it would be less windy than the lakefront trail that I ride. I don't think there was any significant climb on the route but I'm sure there is some

With that, do you think I'll be able to hang with the group going 35+ miles @ 22+mph?
Also, please advise where I'd need to pull myself up to if I did want to ride with those groups?

Just go out and try it. It's really the only option. You may be underselling yourself and may be able to hang with the group just fine. Only one way to find out. I think the reason I've been able to rider longer distances and faster, is by getting dropped. If I just rode with the same group and never tried anything faster and got dropped by people who are much faster than me, I'd never progress. In the first months of riding, I joined a group ride that was 60 miles at 23+ mph. I got dropped after the first 5 miles but hey, I kept training and can finish that ride without a problem. I think getting dropped is actually a good thing, it can be a wake up call for some people.

That is really the only answer anybody on here could give you. Find out the route and print a map of it in case you get dropped, and bring you phone and use it's GPS. Just do it and see what happens.

I suspect the speed you are mentioning aren't actual average speeds for the entire ride, but rather the typical speed you might see looking at you computer while on the flat. Assuming undulating terrain, 20mph avg can be pretty tough. 22 avg can be really tough. Try it and see.

It's impossible to say. 22+, may mean the group cruises around 22-23mph. It also may mean, we average 22mph or better, and often get going in the high 20's or low 30's.

Those are two very different things.

It also may be a group that goes a pretty steady 23 mph, or it may be a group that has constant surges and attacks.

And there may be hills, and if there are hills, it may be a group that waits for everyone at the top, or at least does a rolling regroup, or it may be a group that eats its young.

The fitness and skill required will vary greatly depending on where this ride fits into the above referenced continuim.

As said above only one way to find out.

I don't really know a good way around just going out and trying it. I ride with a group that averages 17-18mph, but its pretty easy to get dropped on the 30mph sprints and small hills where everyone suddenly starts hammering. They are a great group though and regroup after hard efforts and I've never seen them leave anyone behind unless the person getting dropped tells them to go on. Every group has its own dynamics - published numbers are only a small part of it.

How much pacemaking did you do on the casual ride?

another thing to consider when moving up to faster, more experienced rider groups, is your own level of awareness, understnading and confidence.
Loose groups, where you're riding at a very conversational pace, are a whole different thing from groups which maintain a faster pace, tighter formation and surge more often.
Be quite sure of your group riding skills, as relates to knowing how to hold a wheel, hold a steady line, how to read riders ahead of you and any number of other skills important to both your and the others safety. If it's an experienced group, they'll use hand signals and not much/any verbal - a good thing to acquire quickly.
That said, there's nothing like giving it a go. But be prepared to tail off if you start feelin sketchy. It's better to do partial rides until you get comfortable with needed new skills. Watch the guys who are obviously well skilled and experienced. Work on steady and preditcable more than fast. But don;t be afraid to push yourself when the goin gets tough.
You're in a group, yes, but remember only you are responsible for your ride.

It will also be harder to hang if you don't know the route.

I've found not knowing my way back, is worth about 25 watts FTP from the fear of getting lost if you drop.

To quote Smashmouth, you'll never know if you don't go.

My advice is to show up with a cellphone and a map or GPS and all the stuff you'd need for a solo ride (food, water, tube, pump, etc.). When you get to the start, try to find someone who looks like the ride leader or an experienced rider and ask whether there are any parts of the ride you should be aware of: sprint lines, hills, crosswind sections, bad pavement sections, regroup points, etc. Every ride is different.

I wouldn't chance it.

Better off never knowing , never surprising yourself, never having a great ride, than to take a chance at failing.

Important! I got dropped and then lost on one of the airport river rides during my first few times, having my iPhone was pretty damn crucial to getting home!

I did my first group ride about a week ago. The website of the LBS said 12-14 MPH average and 50 miles. The week previous I did 13.8 MPH over 37 miles so I thought I could buck up and do the extra 13 miles... Yeah, those guys were doing 18-20 MPH and were quite comfortable climbing....I wasn't and I'm a big fatty at 270 so while I could keep up on the flats, they lost me on the hills every time. YMMV

Just the usual group ride advice. Try to match your cadence to the rider(s) in front of you. There will be accelerations. Hold your wheel until the blood starts from your eye sockets. It's the only way. If you're barely hanging on the back of the line, drop back a length as the old leader drops back. He'll drop in front of you. There will often be a pack reshuffle at left turns or the tops of climbs. If you don't like the wheel you've been on, you might be able to choose a different one. Ride 6" to one side of your wheel, the opposite to what your wheel is doing. Don't get overlap. Maintain situational awareness. Ride smoothly. If they are advertising 22 on the flat, they are going to climb very strongly. If you aren't used to climbing, being a path rider, you need to start doing some intervals besides the one during which you get dropped. If you do get dropped on a climb, do not give up. Hold the same effort as you go over the top and up through the gears in the drops. Good chance they'll sit up and you'll get back on. A few of those and you'll be cooked, but it's good training.

If you want to have as good an idea as is possible without actually going out and chancing it, try a solo ride for the length and speed that you expect for the group ride. You'll expend about 20 percent more energy riding solo than you will in a group, so if you can do that at the advertised speed, you know you're good to go. Of course, this requires having a cycling computer where you can measure your time, distance and speed.

No, just a typical nervous new rider.

Before going, familiarize yourself with the area and if possible get the route. If it's a reasonable size group someone should be posting their rides on Strava and you should be able to figure out the area they ride in. Once you're familiar with the area, you won't need to worry about getting dropped. Consider the ride as an adventure for a morning. If you stay with the group, great. If not, you get a solo ride in a new area.

Zero risk, just try it.

No, you do not sound like a complete idiot. That usually takes practice.

Go for it, as others have suggested. If possible to ask them how they feel, but if they're not a hard core, eat their own young, drop the weak sort of group, you should be fine, surely they'll at least spot you some clue as to how to get back to base camp.

Pffft. People did this long before cell phones existed. Stuff happens, you deal with it.

There is a group for every level of experience. Ride with the group and if they are too fast, try another group until you conditioning improves and try the faster group again.

Jump in and give it a try.
If you are riding in an area that you are unfamiliar with and getting dropped may mean not knowing the way back to the car carry a small map of the area. I've done that for many years when planning out new training routes in unfamiliar areas...no fun when that 30 mile out and back nears 50 miles because you are on unfamiliar roads and unsure of directions.
I've used area maps, photo copied the section I was going to explore, highlight the planned route, cut it to pocket size and pop it into my jersey pocket. It has been helpful.

The 30 mph sprints and small hills are easy to cover. It's the long 26+ mph paceline that shoves people (especially new cyclists) out the back. If the OP does average 18 mph solo, I reckon he will be absolutely fine on the 22 mph group ride. I also rode in very flat and very windy places. Davis and Champaign.

My 22+ group is horrible. All young guys. Racers. It's a very loose and chatty 16-18mph for 20 miles, then 40 miles at 22+, with very, very hard attacks on every hill, fast descents into strung out 25mph+ pacelines that last for 10 minutes and then back down to cruising at 20 and then smashing up a hill and repeat that 15 times, and you get back and your average for 55-60 miles is 21.3mph and yet it feels like you just were putting out so much more effort.

I can only hang with those guys for the easy part and then maybe 8-10 miles of the 22mph+ pace with the attacking, then I ride 20-30 solo "junk" miles and that's my group ride now.

Where I used to live it was pancake flat and I rode with old folks and I was the World Champion and if we road a 21.3mph average it was like nothing because it was just a nice strong ride down the road among friends.

Depends what your group is like. But the question definitely can't be answered in an internet forum, homie!!!

This would be true where it's a steady speed. But many rides have a very mellow, neutral roll out and then you hit the start (which by the way will be a signpost or a guardrail or a tree or even a line where the pavement color changes) and then it's on like Donkey Kong. If you're not ready and able to match the surge and get in the draft, you'll be off the back before you know what's happened.

Which is why I recommend asking what's up at the start and being self-sufficient in any case.

Ok, here is an update.
Yesterday, I went out to a local group ride that stated 20 miles @ 15~20 mph
I've been to this group before so I knew that there were some strong riders and some beginners like myself.
Due to the number of people that showed up(10) and the path riding we had to do, the group separated into two and I tried my luck with the stronger group.
This group started easy but around 3 miles in they started picking up the pace and the speed was anywhere from 22~28 mph to the turn at 10 mile mark. Same thing coming back.
I was able to hang with the group but I kept failing to notice when the pace picked up until they started pulling away rapidly and would catch up to them either when they slowed down to cruising speed at around 22 mph or I push my rear and burn myself to death every push to catch up right away. Once caught up, I was okay hanging with the group; not saying it was a breeze but I was okay.
Not having the sense to see the push right away made me fall about 5 bike lengths away every time and that made the whole effort so much harder without any draft on windy trail.
Even when I caught up, I knew I spent more energy than I needed to and when the next push came, I started to fall back again only to catch up expending more energy than I needed to.
All in all, I was able to hang but then again, at a cost of a lot of unnecessary effort.
Once we were done with 20 miles, I felt I still had enough gas to go another 10~15 miles.
With that said, I think I may hold off on joining the group ride I mentioned in the OP due to the fact that I'm almost positive they will be pushing harder and longer and I've learned that I need more practice to recognize certain situations in the group ride.
Thanks for all of the advice and any more tips on group rides are also welcome!