Here's a list of some favorites:
Onset: Plenty of room to anchor, good holding, great place to wait out he Canal.
Provincetown: Plenty of moorings, and plenty of room to anchor, great place to visit.
Gloucester: Calm night with nothing from the east, Sandy bay outside Rockport to anchor, easterlies, go into Gloucester and stay either at Eastern Point Yacht club or go into deeper into the harbor and get a mooring from the harbormaster, or dock at one of the restaurants.
Annisquam: Assuming your mast it too tall for the 65' bridge, if not, don't go at low tide, go around.
Isle of Shoals: Good weekdays, may be too crowded for a mooring on the weekend. The bottom can be like a pool table, not good for anchoring. Alternative is a few miles away in Portsmouth, if you need a marina by then, Wentworth is nice (pricey), or go up the back channel near the navy base and get a mooring.
Biddeford: Great stop on the way up, you'll probably need to anchor given your size, but the Biddeford Yacht Club has a couple of moorings that might take you.
Casco Bay: Too many places to list. Need some city, go to Portland. Need to some quiet, try places like the Basin, want a resort try Sebasco. Many times we just pass Casco on the way, because the further east you get the better in our minds, but there are LOTS of great stops here.
Booth Bay: Too many places to list. Moorings or docks at the various water front hotels. Good place to provision, tie up, and wash down the boat.
Tenants: Gateway to Penobscot. You might need to anchor outside if Cod's End's moorings are too tight for your length, but some of them can take you. Cruise around and pick one with some swing space.
Camden: The outer mooring field can take handle your size. Want to tie up, call Willies Wharf WAY in advance. Great place to watch the action, and they can fit you, but you might want to call now for next year. Ask to meet MR Willie.
Bucks Harbor: Some moorings can take you, there is room to anchor as the schooners do, try the outside showers.
Swans Island: Plenty of room to anchor in Burnt Coat.
Bass Harbor: Morris has some big moorings.
Frenchboro: one or two of the moorings will take your boat, you can anchor but the holding ground outside the mooring field is questionable. Close to Swans if it doesn't work out. Have lobsta dinner here, outside, bring in a bottle of wine as the sun sets and you look back at Mt Desert.
Bar Harbor: No problem with moorings, lots of tourist action.
Vinalhaven: They did kinda fill up Perry Creek with moorings, too bad, but there is room to anchor, and I think a couple of the moorings would work for you. Plenty of space to anchor outside as a fallback, Seal Cove, Carvers, etc.
Northhaven: Anchor in Pulpit, plenty of room, great view of Camden Hills.
And there are many, many, many more possibilities. You can hop the coast, or go directly from the canal and do an overnight. Either way works great. Given the prevailing SW, hopping back makes a lot of sense. I only wish the boat wasn't put away, it was early August, and I was on my way right now!
Is this really the end of October. I am depressed!