We will be landing and departing from Boston and already have lodging reserved there. Is advanced reservations necessary for this time of year or can we book as we go? Like upscale places..luxury (we are on vacation!). Want to drive around New England, stopping for probably one night in each location. Would appreciate input regarding mid-late October. Thanks

This is prime time for the New England area and would definitely suggest reservations.

In northern New England (northern Vermont, the NH White Mountains), foliage is usually well past its peak by late October, so you will probably have better luck getting reservations at the better places. In more southern New England, you will need to make your reservations ASAP. During the peak of the leaf peeping season, almost every place--luxury or basic--is fully booked. I would NOT suggest winging a trip at that time, esp. if you only plan to spend one night in each place. Be aware, too, that many of the best places may require a more than one night's stay over week-ends during "prime time" like the fall foliage and holiday seasons.

The Head of the Charles Regatta is the weekend of Oct 19-21. This is the American equivalent of Henley. Hotel space will be scarce in Boston during this period. It is a good time to view the hinterlands.

For that time period I would suggest touring southern New England. Perhaps staying in Providence and enjoying the wonderful restaurants in that city. I've seen decent color in RI as late as Oct 23 one year but this year color might be early. Or for the first part of the week try Portsmouth NH. Haven't stayed at Wentworth by the Sea but it's definitely a beautiful hotel and Portsmouth has some wonderful restaurants. Color won't peak as early on the coast as it does inland and at higher elevations. Even NH's White Mountains could be a day trip from Portsmouth but check first to see if there are any leaves left on the trees.