There are two major parking garages in the old port, one on Fore St. and one on Pearl St. They are near all of the stores.

EVO on Fore St was excellent and fun, small plates, eclectic food, good beer and wine, little pricey but worth it. Central Provisions on Fore St also was a good one and Andy's down on Commercial St.

So much depends on the dog and on what you want to do while you are in the Old Port. The Old Port area is famed for its diverse places to shop, dine, and drink. A dog may more OK for some, less OK for others. Exchange Street, in Old Port's heart, has two pocket parks; another is on Commercial Street near Casco Bay Lines. In high season, local summer traffic can be intense at times, both on sidewalks and on streets, and it's not limited just to rush hour times, but extends well into evenings. Early June should be a little less thronged than other summer months. Best of luck to you!

You'll have a wonderful time in Bangor as well as Portland. There are trolleys in Portland that do a combination 1-2 hour trolley trip through the historic spots of Portland which are tremendously informative and cover the entire town in an open-air trolley. They do a short 15 minute stop at one of the best lighthouses surrounded by wonderful gardens... you can even get a lobster roll there at one of the food stands. Then, the boat trip provides a cruise which shows you all of the lighthouses from the ocean-side. It has clean bathrooms, a bar with mixed drinks/beer/wine/soft drinks and light snacks. You can sit outside or inside. In all cases, the views are great. Check my reviews on Portland and Bangor for more details.

I visited Portland Maine at the beginning of October (2018) and stayed in the Holiday Inn by the bay, it was fabulous and all the staff were friendly and helpful, we had a fridge and a microwave in our room, which was helpful as we stayed their for a week

To give a proper answer this traveller must make his question clearer.

Yes they are!

Shops are open later. Especially in the summer. There are a lot of local places all throughout the old port. Tons of restaurants which a lot are open late as well. Good night life as well. Whether you want to go to a pub or dancing it's down there.

Some cobblestone in old port shopping area, but should be able to navigate around them. Shops are small, boutique style, not typically very wide once off the Main Street. Main drag has sidewalks and crosswalks and should be able to find a restaurant that can suit tastes and serve needs. As to the actual warf, not really the attraction of old port IMO. There should be access near the fairy, but other sections may not be accessible. Hope that helps :)