One night in Salem. . .
I begin to worry that I sound like a broken record. Still I have to recommend The Crooked House Bistro. Salem has other nice restaurants but Crooked House is the only one I'm aware of that could hold it's own in a major market. I gather from your handle that you are a wine lover and Bernard always has something I enjoy. His selections are either excellent local pinots or French.
To the point that you might consider Portland I can only reply that we love the Portland dining scene but friends come from there to enjoy the food and ambiance at Crooked House with us and are invariably pleased that they do.
I understand that there's little incentive to come to Salem but I'd love to hear the impressions of someone else who spends an evening with Bernard and his family. Please consider giving them a try and let us know what you think.
I'd encourage others to make the trip and see what I mean....
No need to go all the way to Portland, there are some very nice restaurants in Salem.
I've been to Bentley's many times and have enjoyed every meal. Orupa and La Capitale are really nice, and Gamberetti's on the ground floor of Pringle Parkade is just a block away and has a great Lobster Fra Diavolo Ravioli dish.
Any of those can actually be walked to from The Grand, and they all have online menus.
If you're in the mood for something specific as the time gets closer, let me know and I'll come up with something!