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J1 to ESTA by visiting Canada question

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I am currently working in Lake Placid (Upstate New York) at a summer camp and my program ends on the 18th of August. Me and a friend have purchased a car and plan to do a road trip across the US but as we are only 2 hours max away from Canada we wanted to start there and travel around for at least a week and then work on going across the US. This would be during my grace period however and I've heard such mixed reviews about whether my chances are good to be let back into the country under the ESTA. I am not subject to the 2 year home rule and traveled to the US last year with no issues and left in good standing. I'll have a bank statement to show my funds, flights from California to Montreal around the 10th of October and then flights from Montreal to Newark a few weeks after, then back to the UK to show them. I'll also have a letter from my parents stating they expect me to return and my ESTA has already been approved. I just want to know your guys' thoughts on this and whether anyone on this forum has actually done something similar and succeeded. I do plan on asking the border people before I leave the country but I'm assuming if they say it's ok there is no way for me to get a stamp or something proving this.

Sorry for the long read and thanks for any replies/input you guys have!


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~~moved to visitor visas from student and exchange visas. OP wants to know about issues visiting the USA on the VWP without returning to the UK first~~

You have brains in your head. You have feet in your shoes. You can steer yourself any direction you choose.  - Dr. Seuss


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No way of knowing, worst comes to worst you go across Canada.

“If you know the enemy and know yourself, you need not fear the result of a hundred battles. If you know yourself but not the enemy, for every victory gained you will also suffer a defeat. If you know neither the enemy nor yourself, you will succumb in every battle.”

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