Upstate NY/New England October 2018

Even if you are adding on another week after you are done in Cooperstown, that's an awful lot of places you are trying to cover and you'll be spending a large part of your time just driving and not really stopping long enough to enjoy it all. If your goal is to see fall foliage, you are starting your trip a little bit past peak. The further south you are in New England (think Connecticut/Rhode Island) you might catch some before it's gone - but up north in Vermont's Green Mountains, NH's White Mountains or NY's Adirondacks, not so much. You can find maps online to see when a particular region is past peak or at peak.

If you are not going to be in Boston or in NYC, you'll want to keep the car with you. Honestly, if you are saving Boston for another trip and you are just planning to go for a single night, I'd suggest saving Cape Cod/Nantucket for that time. You could substitute it for something like Newport, RI (see some of the grand mansions there) or maybe head towards Mystic, CT - you can take a quick flight from Westerly, RI or a ferry from Pt. Judith to get over to Block Island, RI for a day trip if the weather is good, or stay overnight - there are still a few of the larger inns open for tourists and it's a nice time of the year if you want to bike around.

Saratoga is a great town. Give yourself time to explore, wander, enjoy good food and drink. Https://www.saratoga.com/things-to-do/. The Hudson Valley is also lovely, with several towns, mansions, places to hike. It is also home to Thomas Cole and Frederic Church whose homes you may enjoy visiting. Here’s a place to start http://travelhudsonvalley.com/

Thanks everyone for the input. Being from near San Diego where it takes only a few hours to drive a couple of hundred miles I had no concept of the travel times there in NE. It appears I will definitely need a car to see the smaller towns. Also, I gather from your comments that we should focus on a specific area and likely leave Nantucket/Cape Cod for when we take our Boston trip in the future. We do hope to see fall colors so will keep following the various websites devoted to that. What about driving over through CT to RI and some of those coastal towns (Newport, etc.)? Then we could ferry down to Long Island thereby avoiding NYC?

I forgot to mention that we will be driving to NJ (I'm told about an hour from Tuxedo) to visit another friend possibly on 10/18.

Your proposed itinerary is a sort of quantum ping pong ball. Proceeding south from the western reaches of the Hudson valley to Rockland and New Jersey , even Mystic and Newport are inconvenient outliers given your time frame . Mystic will be at least three hours from there and Newport another hour from Mystic . Don't misread me , they are both worth visiting , ( having maintained memberships at both Mystic Seaport and The Preservation Society of Newport County for twenty five years ) I spend a fair amount of time there . Given your general routing and your desire to visit West Point , you can go east from Albany to US route 7 toward Bennington Vermont and then south through Williamstown Massachusetts through the Berkshires ( wonderful hiking around Mt Greylock ) and numerous sites worth Seeing , The Norman Rockwell Museum in Stockbridge is just one . This will save you hours of tedious driving along the I95 corridor , and route 7 is a country road , among the most scenic in New England , and peppered with quintessential New England villages . Save the coast for a future trip . Writing from Firenze ,Italy .

https://www.amazon.com/Along-Route-Journey-Through-Western/dp/0764333720?ref=silk_at_search take a look at this to whet your appetite .

I second the suggestion to drive east to Bennington, Vermont, then south to the Berkshires, where there is plenty to enjoy, including famous writers' homes (Edith Wharton, Melville, others) and loads of scenic back roads, including country stores, covered bridges and village greens with white steepled churches.

In that area, Columbus Day weekend is usually peak foliage, but it depends on the year's weather. If you keep south to the Connecticut Berkshires, you're likely to hit nice foliage even if farther north it's already passed.

Be aware, though, that October weekends are likely to be all booked up already in the area. Weekdays you should be OK if you do the research and reserve now.

Taking a break from a visit to The Uffizi , here are two examples of places that Marcia brought to your attention - country stores : Baldwin's in West Stockbridge MA - https://www.bing.com/search?q=baldwins+west+stockbridge+ma&qs=n&form=QBRE&sp=-1&pq=baldwins+west+stockbridge+ma&sc=0-28&sk=&cvid=B6DB52672EB54DF2A8F1136322F1C1C4 the vanilla extract is the best ! And a good example of a New England covered bridge , in West Cornwall CT , right on RT 7 , truly iconic - https://en.m.wikipedia.org/wiki/West_Cornwall_Covered_Bridge

There's quite a bit to explore in the Hudson Valley between Albany and NYC. Two examples, among many: Hyde Park (home of FDR); Rhinebeck (Aerodrome with WW1 planes in working condition). Plus, beautiful views.