Entering Montreal from the USA
 

How much time should we expect it to take to cross the border from the USA into Montreal? We were told that the crossing has "delays". Thank you!

You can check waiting times at this website from the Canadian Border Services Agency:

http://www.cbsa-asfc.gc.ca/general/times/menu-e.html

it varies. Last Sunday afternoon when I went through at Highgate Springs, VT (I-89) it took about half an hour and there was a line going back to the US, too. It can take longer than this. I am not so familiar with the crossing in NY but I know it can also be slow.
We sometimes go west of Highgate Springs to one of the small crossings at rousse's point or west of RP, then cross over to I-87. This is easy to do if you have decent maps of Vt/NY/Quebec province. there are very seldom more than 1 or 2 other cars at these crossings--usually none

We went through on June 14th and 17th at Magog (I-91 North from VT to 55 North in Canada) and there were no other cars either time.

Depends on the day of the week, time
of the day, etc. Then it just depends on how many trucks are in line, what kind of ID the people in front of you have, any other problems...
It's a very busy crossing, so there are ALWAYS delays.
In my experience, always on weekend mornings in the summer--about 30 minutes

My DH and I have travelled regularly to the US to visit family. From our experience, crossing into Canada is much quicker than crossing into the States, regardless of the border crossing.

This weekend we went down to Massachusetts. On the way down on Friday, we went through Stanstead (Derby, Vt. - Hwy 91) and we waited 2 hours. The lines were filled with motorcyclists going down to NH for a motorcycle weekend. It was a nightmare. Yesterday, we decided to cross back at Burlington. We waited 1 minute.

Lacolle is the biggest border crossing and we've had to wait on both sides of the border. Depending on where you're coming from and what's convenient, I'd pick Burlington.