We generally drive the Taconic as well when we head up to the Berkshires, although not if the weather is bad. It is windy and hilly and there are speed traps which our daughter found out the hard way, driving up to see her boyfriend in the Berkshires one summer.

In Ogunquit our preference is the Gorges Grant which is a bit farther walk to town but we enjoy that as we hope that we are walking off our dinner. What we like about this place other than immaculately clean and friendly and helpful staff is that the comfortable outdoor pool is in the back of the hotel, not out front. Also as on the north side of town, when you drive to Kennebunkport or Portland, you are avoiding any town traffic. Their sister hotel the Juniper Hill is closer to much of the main part of town and we stayed there years ago when our kids were younger. Both have indoor pools.

So it really depends on where you want to stop and plan your drive or plan your drive and decide from that where you want to stop.

Above post I meant to say winding.. not windy although it can easily be windy as well. There are also local roads that allow residents to enter and exit the highway so watch for those.

One thing that is cool and handy about New England is how small the states are. You could hit a corner or MA, NH, VT, ME in a day if you wanted to :-)

How right you are. I lived where NY, Mass, and Vermont almost meet. I could walk from my front door in the NY part of the Berkshires to Mass in under 5 minutes.

Southern Maine
 

I live in southern Maine. It's already crowded here, so if you plan to come this summer, make your reservations ASAP. Beachside towns include Ogunquit (gorgeous beach and Marginal Way), York (3 beaches, family friendly, beautiful town, and Kennebunk. Kennebunk is nice, but I wouldn't base myself there, especially if you are looking for nice beaches. All of these towns are within easy reach of each other. And you day trip to Portland, Portsmouth, NH, Newburyport, MA, Kennebunkport and other places, all within an hour. Just remember that it's really busy here in the summer right through Indigenous Peoples Day!