Where Oh Where...

So... one of my good friends got engaged at right about the same time as I did and because of the proximity of our engagements we've been swapping resources and ideas. We both have booked the same photographer, All Angles. Included in our package is an engagment session as I'm super excited about taking engagement pictures as I am obsessed with pictures, scrapbooking, you name it, I love it! But I have a huge dilemma coming up. My friend is already talking with the photographer about when and where she is planning to have her engagement pics taken. I'm so torn because I'm not sure when would be the best time of the year to book it and what types of settings I want.

So these are the ideas I'm playing with:

I L-O-V-E the fall season, I was born in Novemeber, our wedding is going to be in October and the outdoors is sooo beautiful.

I also love the country/rustic/outdoor/farm-ish look as well. I really like black 4 post fences and in the proper setting I think they could make a beautiful backdrop.

I also like the playfulness associated with playgrounds. I think it would be really neat to incorporate a tree swing. It would add fun and simplicity.

Ok, I know this is kinda weird, but I know of a friend who had his and his fiance's engagement pictures taken at a train trestle. This particular train trestle is literally a few miles from my house and I think it's a really neat idea. And no, we wouldn't be walking ON the trestle-that's just dangerous. But the supports come down to a road and a field that passes underneath where we would take the pics. The trestle is very rusty and surrounded by trees, I think it would be a cool element in the pics.

I'm also toying with the idea of taking pics at waterfront park and subsequently in the downtown area. I feel like it's a little cliche but the pics that I've seen are so gorgeous it might just be worth it!

Any suggestions? What do you think?