Since I like to photograph people in locations outside of the studio, I try to keep my eyes open for locations with multiple backgrounds. I find that most people think portraits are taken in a studio with nice lighting in front of seamless backgrounds. But this creates a "sameness" that I don't enjoy. You don't want all your photos to look like your subjects were standing in a long line, waiting their turn to step in front of your camera. I want lots of different backgrounds in a more casual setting. What do you look for? You want an area where you can move your subjects as little as possible and have very different scenery behind your subject. I look for ease of access because most folks don't want to have to trek a couple of miles to get to your outdoor studio. Unless you have a landowner's permission to use his property, you want public property. You don't want it to be in an area that is so popular that you'll have a constant audience or, worse yet, people walking through your scene. One of my current favorite locations is near the Manassas battlefield. There are lots of paths, trees, creeks, split-rail fencing, and foot bridges within 100 yards of each other. There are many such locations around your house, too. It doesn't have to be out in the trees. My favorite city of Augsburg, Germany, had a downtown area with old buildings, train stops, car garages, and parks that I used for years with my models and clients. You get the idea.
Use the various backgrounds to give your subjects different looks. I usually have the models bring several different shirts (since most people seem to prefer head-and-shoulder photos). If I have a place for models to change, I'll have them bring completely different wardrobes.
You may worry about lugging all the extra gear, but you easily do these photos with an off-camera flash and a reflector or two. That certainly won't add too much weight to your load.
I shot this last shot outside the Georgetown Mall, after the Kelby Worldwide Photowalk. We were there recovering from the heat and a friend who lived nearby came by for an impromptu shoot. We walked just outside the canal entrance; popped open a couple of reflectors; and completed the entire shoot in just under ten minutes. Quick, easy, and she liked the photos. That always makes for a good day. Have fun.