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When did your kid stop crying for daycare/school drop off?
We put DS in a nursery school two mornings a week and, as we expected, it's taking some time for him to adjust. He hasn't really been away from me, unless I leave him with family. He tends to be shy around other kids until he feels comfortable. So it just seems like he's getting worse, not better, everytime I drop him off. Today he started crying as soon as we hit the parking lot. I just feel like he's always going to cry and he'll never like it! Everyone tells me eventually they do love it, I just am not sure. It's only been two weeks, so I'm probably just jumping the gun by saying it won't get better. It just makes me feel sad and horrible every time I leave him hysterical. 
When did your toddler stop crying and adjust to school or daycare?!?
Re: When did your kid stop crying for daycare/school drop off?
Stephanie has never cried once when I dropped her off from the time she was 3 months old until now (almost 5). Some days she's a little clingy and more affectionate with goodbyes but I don't recall many tears.
Evan on the other hand has been a more sensitive child and terribly clingy. In the infant room he never cried but developed terrible stranger/separation anxiety around 8 months or so. When he transitioned to the toddler class at 11 months it was terrible and he would cry as soon as we went in there. (they transitioned him for 2 weeks). He eventually stopped. Now all of a sudden for the last 3 weeks he flips his sh*t and cries and tantrums when I drop him off (he will go into the corner of the room, drop to the floor and bang his head. It is getting old and I am getting frustrated with it. (the staff in the toddler room are way different than the ones he had as an infant). They tell me that after I go he eventually stops crying. I can only hope that is true.
GL, I hope it gets easier for you. I think most kids go through a phase...I am waiting for the phase to end soon as well!
Mommy to Stephanie Lena - 2.13.07 and Evan Ralph - 9.23.10
Angel Baby (m/c at 9 weeks) - 1.2.09
Christmas Card Picture - 2011
(aka: the only picture I could get of them together that was not blurry and had them both sitting still!)
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The Stephanie Song...click here to listen!
It's hard when they only go for 2 days out of the week. It's going to take longer for him to get adjusted. The longest time it took for a child in my room to get over the anxiety at drop off (who was part time) was about a month.
It really does make it an easier transition if you don't stay that long. The longer you stay for goodbyes, the longer the crying goes on after you leave. I know it's hard to drop and go, but it's really best (speaking from a teacher perspective). Even though it's been two weeks, to him it's only been 4 days in a new place. He needs to learn that you will come back for him.
Oh yea, I only stay for 5 mins or so. I just tell him mommy will be back soon and I love him and he'll have fun. When I called before, they said today he only cried for 20 mins after I left. So I guess that's progress compared to the hour he cried the 1st day!?!
We changed daycare/preschool this past summer. To prep her we read "Llama Llama misses Mama." It's all about being new at school and being lonely, but finding new friends and Mama Llama always comes back. Whenever she looks tentative, I tell her "Mama Llama always come back" and usually does the trick.
My boy (who'd just turned 3) cried at orientation for a couple of minutes and then didn't do it again.(like your son he does hang back a bit if he's uncomfortable) I DID make allowances for his adaptation at school though. Like your son he'd never been away from me for anything like this. Our school has a car line where you drive up and the teachers take the kids from the cars. For the first month or so of school (2 days a week) I'd park and walk J to his classroom. Then I'd park and walk him to the door. Then after 6 weeks of school I announced "OK today we'll use the car line" he whined and cried a bit until I told him we would listen to his music in the car on the way to school if he did the car line without complaint. Done and Dusted, he did the car line and hasn't looked back since (seriously I'm yelling out the car windows GOODBYE SWEETIE! and he barely turns his head.)
I guess my advice is ease him into it slowly, give each other a chance to get used to it. and I promise he won't cry forever. Hang in there, it just takes a little time.
All the best- G