Best is to visit their website and most queries get answered. I have been there.Its quite a relaxing walk.

There are a number of cruises that will take you out to the islands, or more specifically out fishing. I'm sure that anyone, regardless of age would enjoy doing this. The visitors center can help in directing you to the desired cruise.

We stayed outside of Plymouth proper so I don't know much about the in-town accommodatations, but along Water Street you can see much of what the Pilgrims saw. If you want to really understand the evolution of the settlement, take the walking tour from the Jenny Museum. As far as staying in the historic center of town, I think that's virtually impossible now, as little remains, but it's still a stirring memory of early days of our history, and worth a visit.

We stayed at the Best Western. It was within walking distance to the waterfront and the historic district and very close to the beach. We ate at a restaurant named Martini's and it was excellent; highly recommend. It is on the main street with the shops.

There were a lot of people with dogs walking around the waterfront. I imagine that in October the things you would want to do our the indoor area - restaurants, museums, stores. i didn't see any dogs in any of those places. We walked the entire historic area an drove around the other area and didn't see a doggie day care. I would Google to see if there is one in the area.