WE ARE TWO COUPLES IN OUR 50s AND WE PLAN TO SPEND A WEEK IN MAY DRIVING FROM NEW YORK THROUGH CONNECTICUT, MASSACHUSETTS, VERMONT AND CANADA TO NIAGARA FALLS AND BACK TO NEW YORK. WHERE WOULD YOU RECOMMEND TO STAY AND WHAT SIGHTS ARE ALONG THE WAY? WE THOUGHT TO BOOK AS WE GO. WOULD THIS BE VIABLE?
I. MCMARTIN, LIVERPOOL
Google "National Geographic Ultimate Road Trips" to find several drives, including one along New York's Hudson River Valley, another through the state's Finger Lakes, a drive through Montreal's wine country and another through Pennsylvania that you can stitch together and help you plan this trip in detail. If you follow the Hudson River Valley out of New York, once you get close to southern Massachusetts, Route 7 leads north through the gorgeous Berkshires into southern Vermont, then you turn slightly east to pick up Vermont Route 100, a narrow, wandering sylph of a road rated one of the loveliest drives in the country. The road ends at Newport, on the Canadian border. From there you can cross to Montreal, then Niagara Falls and back to New York City. This is a lot to fit in, however. If I were you I'd forget Canada and turn east out of Vermont and explore Cape Cod, then head back to New York City.
There's so much to see in this part of the world it's not possible to construct a definitive list. It depends on your interests. My own list would include West Point, Hancock Shaker Village, the Norman Rockwell Museum, Green Mountains National Park and the villages of Rhinebeck, Great Barrington, Stockbridge and Grafton and the grounds of Harvard University.
In May you should be fine to book accommodation as you go.