Will CBSA and US Customs and Border agents cause me problems?
 

Right now I'm in the US and I'm thinking of taking the train from NYC to Montreal and then going through Toronto to Niagara Falls (Canada and US). My flight back to Canada is from HOU. The problem is that CBSA tends to hassle me everytime I come back to this country. I don't know why because I don't have a criminal record nor have I ever lied to customs. On my last entry back into Canada, the agent flipped through my passport and asked why I have travelled so much given that my passport is relatively new. I thought it was a very bizarre question to ask, but nonetheless, I answered it. After the agent was satisfied with my response, he let me through. This is pretty much why I'm considering abandoning plans to visit eastern Canada and just stay in the US until I'm scheduled to fly back to Canada. So having said that, should I reconsider? I really want to visit Montreal and Ottawa. I've been told the Amtrak train from NYC to Montreal is really nice and worth taking.

My concern with US Border agents is that they might get suspicious on why I'm re-entering the US after leaving for Montreal. Of course I'll explain to them that I want to visit Montreal and the Niagara Falls on the Canadian side. I will also mention that my flight back to Canada is from the US. However, I'm afraid that they might somehow reject my entry into the US.

As a Canadian or American citizen, frequent border crossings are very common. You will get asked questions but just answer them and you'll be sent on your way. Consider getting NEXUS as well to make the process a little less painful if you plan on crossing the border frequently in the next 5 years.

I am never too worried about the Canadian side as you enter AS OF RIGHT as a Canadian citizen. Yes, they can search your stuff but that's about as far as it goes if you are truthful about what you declare. To be honest, how much you travel (or where you've been or where you work) are none of their business and you don't even have to answer such questions so long as you are willing to be searched. Easier if you just answer everything! DO NOT MAKE THE MISTAKE of thinking that this applies when you cross to the USA as a Canadian as all hell will break loose if you don't answer their questions :)

Just answer truthfully and you'll be fine.

CBSA asking questions regarding your passport and travel is in their right.

Most times just relax and answer their questions. Enjoy the trip!

Cbsa can ask the questions but they can't deny entry to a Canadian citizen if they refuse to answer. They can make your life a pain for a while though :)

AND/OR they can make a notation in your record of being difficult with them.

Back when I was a frequent visitor to TO they used to give me a hard time fairly frequently at the airport because I was always traveling alone and not there to visit anyone in particular but was there as a tourist. This seemed to bother them...like no one could possibly want to be a solo tourist to Toronto so I must be up to no good. I got the pink highlighter on my form and secondary screening a few times.

Doubt about the difficult notation - better things to do with their time.