I would go back to the late 50's and fish the outerbanks with my grandparents. I never got the chance to fish with my grandmother beyond me with a snoopy rod. We have some movies they took the first few years they went down there when there was basically nothing but a gas station where the village of Avon is now.
Edit: I chose this based on the premise that I am the only one that gets on the time machine. If I can choose people to go with me it would be different. I just don't want to go back to 1368 by myself
