Cafés. I stumbled upon a great local café called Local Sprouts. This Café is organic and supports local farmers. You can check out a painted map of Maine on the wall of all the local farms you are supporting by eating there while you sit on a cob bench [made of Earth] and sip iced tea from a maison jar.
Museums. I found that the art Museum in the middle of town is free after 5pm on Fridays. I like modern art so this museum wasn’t really my style – it was mostly paintings. It was about four floors of paintings and some other art [including a café].
Stores. There were a lot of cute shops and a nice walk through town. Backpacking stores, pizza shops, books, toys, and much more.
Getting Around: Portland is not big so it’s super easy to walk the entire town a few times. I parked outside of the main streets of the town so that I could parka for free and it was only about a 12 minute walk back to the car.
Must Try: Maine Lobster. Maine is known for it’s Lobster [Although places in Canada say Canadian Lobster is better]… $20 spent at the Lobster Company right on the water will get you a Maine lobster, corn on the cob, a baked potato or fries, and coleslaw. The Lobster Company was a great place to eat on the water with outside tables, outside bar seating overlooking the water, inside tables if it’s chilly, and an outside bar serving drinks.