Finger Lakes, New England Fall Drive and NYC

A couple of ideas to throw out. First I would cross Vermont on Route 4 from Rutland to White River Junction. Very nice in the fall and you can stop and take a lift to the top of Killington Ski area. Very beautiful scenery. Also on the east end of route 4, the views from the bridge over Quechee Gorge are fabulous.
When crossing New Hampshire, be sure to take Kancamagus highway from Lincoln NH to Conway. Again fabulous views.
The most fantastic view in New England is a drive to the top of Mount Washington. This would require a drive north of North Conway.
When traveling from Kennebec south, I would take coastal Route 1. Route 1 takes you thru small New England towns all the way to Boston. Interesting towns on the Maine and New Hampshire coast are Freeport (home to LL Bean open 24 hours a day 365 days a year), York Maine, (Cape Nedick Light House, the most photographed lighthouse in America.) Portsmouth NH. However if you look for signs there is coastal route 1 (aka route 1a) that will take you along the beach from Portsmouth to the Massachusetts border.
Go around Boston on I95 when heading to the cape, unless you want to stop in Boston.
From NYC take Route 9 once you are out of the city and follow the Hudson river north via Route 9. Many nice spots to stop enroute to Albany. West Point, Bear Mountain, and Hyde Park N, home to the Roosevelt (FDR) estate.
I would drop the car in Albany and take the train back to New York City. Once in the city you should not need (or want) a car.
In NYC, my favorite spots are St John's Cathedral, the Cloisters, Metropolitan Museum of Art and a round trip on the Staten ISland Ferry (free but gives you GREAT view of New York Harbor and the Statue of Liberty).
Your trip is very ambitious for not wanting to drive more than 4 hours in a day. You may need to be a little flexible

You do have potentially a lot of driving. Sandwich is a little close to Boston to set you up well for Cape Cod--the most interesting places tend to be further East. I'd skip the Hudson Valley and turn your Kennebunkport day into the coastal drive suggested above.

You may get fall colors throughout your trip, although the intensity will vary. The finger lakes are may be too cool for some of the usual activities like boating. Corning is notable for its glass museum. You might stop off in Ithaca or Chautauqua, although I'd imagine that the latter is more active with cultural events on weekends.

Fall is expensive in NYC--you'll pay less outside of Manhattan and all the major chain/franchises have properties in Brooklyn and parts of Queens like Long Island City. Also consider Jersey City, Fort Lee (conevnient to George Washington Bridge) and Newark--the Hilton connects to Penn Station & connections to WTC (via PATH) or midtown (PATH and NJ Transit Trains).

October weekends mean a lot of people looking for colors.

You really won't have much time for hiking/walking, except at Acadia and in NYC. Brooklyn--DUMBO/Brooklyn Heights (views of Mnahattan); Williamsburg (art--galleries open on weekends) are the most accessible.

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