Need help with night time lighting

I am going to be photographing people as they are about to go on a carriage ride. This will be at night, and the location of the photograph will be constantly changing depending on where the carriage starts out at. The general area where the carriages park is an open parking lot, so no option for bouncing flash. Since I will be having to move all around the parking lot, a large softbox or umbrella is not really practical, not to mention that it is now winter time, and more than likely there will be a strong wind blowing. (Tough enough scenario? )

So my thoughts are to pump up my ISO to either 1600 or 3200 with a SS of around 1/60 to let in some of the ambient Christmas lights that will be in the background, and just use a bare flash with TTL, on a stand right beside me that I can easily take with me from location to location. Yes, this will be harsh, but it's not a formal portrait, just capturing the moment, so to speak.

I consider myself very proficient with the use of off camera flash, and maybe I am trying to make this tougher than it needs to be, but if anybody has any suggestions as to how I can keep my subjects from looking like a "deer in the headlights" I would really appreciate it.

Thanks.


Edit:
Here is a sample shot I took at the location the other night to show ambient. This is at ISO 3200 f/3.5, 1/80. I figure for some group shots I will probably have to close my aperture down to f/5.6 or even smaller.

IMAGE LINK: https://flic.kr/p/BsRS​jf

IMAGE LINK: https://flic.kr/p/BCrt​hK

The easiest solution for achieving what you want to do is to bring your daughter or another assistant and have them carry one off camera light firing thru a small softbox. This will give your lighting a more natural look. You already have the exposure settings down so concentrate on light placement. Of course two lights would be better but since you'll be moving around, it probably isn't practical.

The second solution is to put a small bounce card on your on-camera flash and go with it. This will give you maximum mobility.

Most nights I am doing this will be during the week, so bringing my daughter with me is really not an option. I have thought about using 2 flashes, 1 on a stand beside me, and the other on-camera, but how much help would that be, and would there be issues with cross-shadows?

I have an umbrella, along with an umbrella style softbox that I am going to experiment with. But if the wind is blowing at all, and I have to use a sand bag for support, I am afraid it will be too difficult to quickly move from place to place.

Are you getting paid enough to hire an assistant? If you're having to move around, it will make you so much more efficient and agile -- which will make you look more professional and capable to your employers, not to mention giving you better images. And next year, include the assistant in your budget.

tim1970 wrote in post #17800420
Most nights I am doing this will be during the week, so bringing my daughter with me is really not an option. I have thought about using 2 flashes, 1 on a stand beside me, and the other on-camera, but how much help would that be, and would there be issues with cross-shadows?

I have an umbrella, along with an umbrella style softbox that I am going to experiment with. But if the wind is blowing at all, and I have to use a sand bag for support, I am afraid it will be too difficult to quickly move from place to place.

Why would you put two flashes next to each other? The second flash I mentioned should be used as a backlight to give the photos some depth. Example below.

IMAGE LINK: http://s182.photobucke​t.com …kevin/lupton-462.jpg.html

IMAGE LINK: http://s182.photobucke​t.com …ing/wedding-1378.jpg.html

Definitely bring and assistant, will be worth it ten-fold in the end.