When is Trespassing a Crime

My question involves real estate located in the State of: Connecticut

Here are parts to my states trespass law that seem to apply in my case...

A person commits third degree criminal trespass when, knowing he is not licensed or privileged to do so, he enters or remains in any premises for hunting, trapping, or fishing or enters or remains in premises that are posted in a manner prescribed by law or reasonably likely to come to the attention of intruders or that are fenced or enclosed to exclude intruders. This also applies to state lands near state institutions. This is a class C misdemeanor punishable by up to three months in prison, a fine of up to $500, or both (CGS § 53a-109).

A person commits simple trespass if, knowing he is not licensed or privileged to do so, he enters premises without intent to harm any property. This is an infraction punishable by a fine, currently $77 plus costs and fees if paid by mail (CGS § 53a-110a)

Which one would apply, do you think, if I was riding across an old dirt road on someone's private land in a vehicle, a Jeep for instance, who had clearly posted "No Trespassing" signs on the road from each end?

My opinion for the two cents that it's worth: 109 would apply since you ignored the "no trespassing" sign.

I suspect, however, that if you pled not guilty you might be offered a reduction to 110a since a DA might not want to waste the court's time on a trial over something like this.

Whether that strategy poses any risk to you is something you really need to discuss with a lawyer. Don't try it on your own.