First of all, is this a one way trip? Because if it is, I'm going to have to think about it more, but if I have a time machine that will get me back to modern day and am able to bring things with me, I think dinosaur hunting would be an entertaining enough pasttime.
I'd like to go back to the time of one the great world spanning empires. Just to see how the culture actually operated. I'm thinking either Alexander the Great's Macedonian Empire or Genghis Kahn's Mongol Empire. It would also be interesting to be a spectator at some of their historic battles.
I would be very interested in seeing the transition from ancient Roman republic to ancient Roman empire, specifically to see my favorite historical figure in action(Augustus).
Having enjoyed the history of The War of 1812 in junior high school, and how it shaped both my country and the US, I'd like to visit inter-colonial "Upper Canada" (now Southern Ontario) and see some of the things that went on. The Americans burned down most of the town of "York" which is now known as Toronto. We set fire to the White House. They painted it white to hide the charring. Laura Secord crawled/hiked over many miles of bush, through the Niagra Escarpment, mostly at night, to inform the British of a pending US invasion. Laura Secord Chocolates are named in her honor, and for those of you familiar with the area in Niagra Falls, "Lundy's Lane" was one of the trails she took to reach the british army.
For me, it would be the late 1960's. I would LOVE to have seen the first Woodstock, and I've always been fascinated by Hippie Culture. Heck, if I was around in the 60's, maybe I could have been one of the pioneers of Hockey Night in Canada, or at the very least be calling hockey games on the radio when people still actually sat with their family and listened.
At the moment, the exact time and place I put the original valuations at work in a safe, secure spot that I can now no longer remember. Fuck. Generally, my last day of high school. From there on out, I would have done things a lot differently.
I would like to go to two different time periods. Ancient Rome - Being a history and architecture nut, I would have loved to see everything in Rome be built. If possible, I would also like to jump from around 25 B.C. right when Augustus Caesar was in power and the Forum was developed before jumping to about 125 A.D. after all of the cool architecture like the Pantheon and the Colosseum had been built. It would also require me to have some sort of universal translator so I wouldn't be killed, but I think seeing Rome during these two time periods would be amazing. 1920's America - Not only a cool time period to live in, but I also have heard that people today are a lot larger and more athletic than people in the past. I would have liked to see what I could do against some major league baseball players (doubt I would have been successful since the professional ballplayers back then were just incredible) before jumping to star in the NFL since I would probably be taller, faster, and more athletic than most of the people in the league. Also, to steal from a previous post, ride high on Wall Street and bail out before the crash.
The Old West. There, I would find a little town that is lax on laws, set myself up a brothel and become the most prominent madame in the area. Anyone who thought to fuck with my establishment would be dispatched at the point of my pistol, since if I'm living in the Old West, I will also be learning to shoot everything in sight. Then some days we would go out and hunt for buffalo! But only be able to carry 247lbs back to our wagon. It's the quasi-lawlessness that makes it so awesome. If you can be clever about it, you can get away with it. Plus, much less people around.
I'll have to agree with what a few other have already said and say the 1970's. Specifically a suburb in the Midwest or Texas. I'm thinking Dazed and Confused here. Hanging out drinking beer, smoking a little weed here and there, and going to some awesome concerts. I think even more so, though, I would like to go back to the early 90's. I would follow Phish around the country and catch as many of their shows as I could. That was really their prime in my opinion, from the early 90's untill they went on Hiatus in 2001, and I think the scene would be pretty fun...even though it was full of damned dirty hippies.
Besides the obvious ancient times to see how some of the massive structures and whatnot were truly built, I would probably go with the "Gilded Age" of the early 20th century in America. I have a mini obsession with ridiculous mansions, especially historic ones, so I would love to go back and see what boulevard living was like. Living in Chicago, the South Side is commonly known as less desirable than the North Side, but back then, with Prairie Avenue and the likes, it was the place to be. I've seen pictures of the big open boulevards with the ridiculously opulent mansions of people like Marshall Fields and other industry tycoons of the time in what is now urban blah. Same with areas in Milwaukee, Euclid Avenue in Cleveland, etc... It was a crazy time of over the top spending by the "haves" and if I was just visiting, I would love to see these areas in their heyday. Cause what remains now is almost awkward in its out of place setting, whats not been demolished for more development.
Anytime I have ever thought about time travel I have thought about using it in order to get laid more when I was in high school.
I can't talk about the Jesus era, but............. I was a Rollermaniac. Seriously. Living in Winnipeg as a 10 yr. old in 1975, I was swept up in the movement for several years. My best friend stole ALL of her brother's albums and sold them for money to buy tickets to a Bay City Roller concert for six of us. Of course, I was one of those twits sitting outside their hotel all night, singing their music, screaming, crying and generally annoying every adult within a mile radius. Turns out I'm a creative liar when pressed and bold enough to weasel my way to the front of the stage (our tix were in the nosebleeds of Winnipeg Arena). Shitty about my friend getting pushed against/under the stage so hard her arm was broken. I can't even talk about the day I found out Ian was leaving the group - it's still too painful. I didn't leave my house for over 1 1/2 yrs. without my Roller gear on. The world needed to know of my fierce allegience to the wunders of the BCR, and by-golly, my outfit would show them. Trouble started when I moved to Edmonton in 1977. Turns out that they weren't quite as enthralled with my beloved Rollers as I was. Over the next few months, my tartan and stripes quietly got replaced with more acceptable Junior High wear. I still have all of their albums and have been known to play them while shitfaced at 6am, but don't tell anyone.
1976. Look, let's not kid ourselves - the 60s were too crazy and the 70s was like this nasty disco hangover, but you pick that shit right up at the end and you're golden all the way through the dot-com bubble burst in '00. That's twenty-four years! You'll have to suffer through the tail end of the gas crisis but you know that ends quickly. Get a nice cushy job at an Aerospace company or something and ride that shit out until everything goes to hell in a decade. Get yourself an Atari 2600 and buy yourself a small 4-bedroom house in the suburbs that will octuple in value as the burb gets built out. On the weekends just dress badly and pop in for a movie at the mall. What should you see? Close Encounters? Raiders of the Lost Ark? Yeah, I hear those are good. How about that Star Wars movie? Enjoy the Reagan years with the knowledge that 1) while everything is getting fucked up, nothing seriously bad is going to happen, and 2) you won't have to pay for it until at least like 2000, maybe 2001. Ignore the disco burnouts and the yuppies and enjoy a simpler time.