So my trip is about 5 hours (give or take, stopping for a bite to eat, gas and what not). A friend of mine who brings a Cadillac and I originally did the trip on Friday. Because we want to make the trip a bit casual and not get up super early to hit the road, it felt "rushed". What I mean by that is get on the road, get to Carlisle, clean the cars before dark, be ready for Saturday morning.
We started making our trip on Thursday. No matter WHAT happens, the only goal on Thursday is to get to Carlisle and checked into our hotel, the end. It has worked great for us. We meet for breakfast, casual ride and no rush. One year, I got to deal with a failing alternator before we left the county!
Friday morning, it's stop at the show field, get the car cleaned up at the wash bay. Hang out, check out the stuff on the show field. If any one I know has arrived, say high, hang out. Most of the people I know that show up have shorter commutes, so they arrive Friday afternoon sometime. Once they arrive, we figure out dinner, picture and entertainment plans. A couple of times we end up at two different places (partly because the group can get massive for one place to take on).
As for the actual event, Friday does yield some benefits. They have a schedule of events that are taking place that you can attend with less people to compete for space (such as the Autocross Ride Along).

My opinion for the crew coming from Michigan (and other far distances), if you feel the trip is a big long (maybe more than 5 hours), I would plan to leave Thursday. Keeps it easy, casual and avoids feeling "rushed". This way, even if you arrive at 11:30pm Thursday, you have not missed anything. This gives you a chance to check out Friday at Carlisle for yourself. If this ends up being the only time you go to Carlisle, then you know you did it all. But if you find you want to do it again next year, you now know what to expect and can adjust your plans accordingly.

Thanks for the feedback guys. I think I will be adding Thursday night to my itinerary.

The other thing I'm contemplating is registering for the outdoor show field or applying for the invitational indoor display. Plus I'm not sure if I'm trailering the car or driving. My gut says drive because that's less hassle with no trailer involved but if I do the invitational I'd need to figure out transportation to-from the hotel (which I'm sure somebody would be more than willing to give me a ride). I need to read into the invitational a bit more in the next couple days. I believe Devin said there are NO awards for invitational cars but you do get to keep your display placard they put in front of your car - is that correct? My buddy here in Michigan with the black 86 SS I do a lot of shows with said he's going to apply for the invitational.

Devin, since you've done the invitational before and have the experience, do you mind kind of filling us in on details we should know - basically 'what to expect'?

100%. We'd have your back if you didn't have a ride around because it was inside for the display.

I second that.
Matt - I recently saw you mention that you are debating on staying at a different hotel. To get the rate I got with Sleep Inn, my reservation is non-refundable (so I am not switching up my plans). But if you stay at Sleep Inn, you have plenty of us who can help if needed. To my surprise last year, Sleep Inn was not crowded (all other hotels I have stayed at were jammed full each year with show field participants). I don't know if that is normal for them or not. Only down side to me was that their breakfast area was not as big as another hotel I used.

I may choose to go to this again... Lets invoke the "rain rain go away" ceremonial dance. Heck the 50th Anniversary of The Monte Carlo would be nice as they newer FWD ones typically get no respect anywhere they go. So would be nice to see them showcased Will have to wait and see, get a feel for the moment.

Problem is the FWD Montes for many are daily driver (few are summer only cars). So many of the dailies are leaving the Monte seen and off to another platform. There are a small few of us who have FWD Montes for summer use only.

All my years going to this event, I have yet to see a 5th gen Monte there. I hope we get a strong turn out and awesome blend of all gens of Monte this year! Rain or shine, I have always had a good time.

Yep Maniac you are a die hard for sure. I agree most FWD enthusiasts have moved on to other platforms. Not hard to imagine them doing that with all the muscle cars on the market in the past 10 years. Pretty much anything one wanted they can find, mild to wild. I predict there will never be a 5th Gen. there at the GM Nationals. Ha ha Jedi mind trick for driver3, Sidestreet and others. What a way to make the 1st ever 5th Gen. debut but at the 50th and probably the last anniversary of the Monte Carlo. I wont be around for the 75th anniversary and neither will our cars if we have to get rid of all internal combustion engines. LOL, short sited people. The rest of the world will have them for another 100 years. Rain or shine people rain or shine. Flippin die hards, they show up at just the right time to motivate us all.

The invitational is a cool experience but it has it's downs as well, being without your car all weekend is one of them. Being able to cruise with everyone to eat and such it's nice to have your car and be in that group. Pretty awesome to see all the nice rides going down the road, and not in a passenger seat lol .Also yes, no awards for invites. You do keep the placecard which is actually really good quality and something really cool to have (I have it up on my wall with the trophies from other shows).

For Invitational you have to be there Wednesday or Thursday and you can't get your car out until (well it was Sunday) but i assume Saturday after the awards parade. Not sure which it is now that they are done with Sundays but waiting around all day Sunday while everyone else was already on the way home was a big drag.

That said, it's a great one time experience. They have a huge pizza party Thursday night for all invites with free food and drinks and they have a ceremony thanking you and congratulating you on being invited. Being indoors you know people wont skip over your car looking at it, everyone who goes to Carlisle goes to see the invites. Pictures indoors always look good.

To be honest Matt with how clean your car is, I would put it in the Standard of Excellence judging I honestly think your car would do very very well!

As for Hotel, a good chunk of us stay at the Holiday Inn right in Carlisle, it's a bit more pricey but the location and cleanliness if second to none. A lot of people in our group also stay at the Motel 6 which is right across the street.

As for more people going, i know he isnt active on here anymore but Keane will be going with is Camaro. As well as our friends Tamer with his ZL1 and Bob another 5th gen Camaro. As well as Nate and Lauren with a Chevy Cruze. Pretty much our whole car squad up here in the 607.

I appreciate that buddy and thanks for the feedback! I did just register mine this morning for Class 243: '95-07 Monte Carlo - Stock'. And honestly I'm still deciding if I want to apply for the invitational (appears I have some time to make up my mind).