Some popular locations in the greater Portland Area for photos. Keep in mind that these are meant to be a guide for backdrops only. Different seasons, weather conditions and lighting due to time of year and time of day lead to very different ascetics in photographs that won't necessarily be able to be re-created.
Old Port, Portland in Winter
Some winter scenes around Portland that I found online to give you a feel for how it *could be depending on the snow fall of the season. Note, a lot of these are taken at blue hour.
Going into cafes/pubs, etc can add a nice authenticity to images.
Kettle Cove: Cape Elizabeth
In addition to the rocky seaside, Kettle Cove has some pretty wooded trails.
Bug LightL South Portland
From the Internet on a very wintry day:
4, Portland Head
Portland Head and Fort Williams State Park also offer more interesting locations on the property including rugged shoreline, wooded areas, and cool stone ruins not shown here.
Two Lights State Park: Cape Elizabeth
Maine Audubon Center: Falmouth
Check out some wintry photos here: https://mymaine.org/southern-maine/gilslandfarmauduboncenter
You'd need to be in the treaking frame of mind for this location.
Tidewater Farm in Falmouth:
Photos by Double H Photography
I've not personally shot here but admired the dream like look. Again, in the winter this would be a boots on, walking in the snow type of session.