Fly into Portland, spend a couple of nights exploring the city then drive south to one of the beach areas like Wells, York, Ocean Park, etc. and let the little one have some fun in the sand.

Or, fly into Providence, drive about 45 minutes to the Mystic, CT area, visit the aquarium, Mystic Seaport, take a ride on one of the boats that offers rides into Long Island Sound, visit the shops along the main street by the draw bridge, visit the little park with swings etc. near the bridge, visit the shops in "Olde Mystic Village", eat dinner at Daniel Packer's or the Oyster House, breakfast at Kitchen Little , lunch at Sea Swirl, or Cove Fish Market or over in Stonington Burough at Noahs or on the water or over to Noank at Abbotts. Take a ride to Watch Hill, RI for a ride on the antique merry go round and more good eats or go to the beach there. If you really need adult entertainment, the casinos are 15 to 30 minutes from there.

Here's the perfect thing: Quebec. Spend a few days in Quebec City, then a few more in the Mount St. Ann ski area....it's off season for the ski resorts, so the prices are low - mountains, hiking, cool temps, etc.

Check out Newport, Rhode Island. Right on the water, beautiful colonial architecture everywhere, lots of shopping, dining, and nightlife, close to beaches, mansions, the Cliff Walk, etc. A short drive from Providence or Boston. Unfortunately, the traffic can be quite bad in the summer.

I would also highly recommend the White Mountains in New Hampshire, but it sounds like you want to stay put more than drive around and sightsee... however, the mountains are beautiful and the weather would be relatively cool there (cooler than Newport, although Newport has a sea breeze...). The Lincoln/Woodstock area is just about 2 hours from Boston and 1.5 hours from Manchester, NH. North Conway is a bigger town but farther from Boston; it's about 2 hours from Manchester or an hour and 15 minutes from Portland, ME.

The most comfortable summer weather in New England is probably along the Maine coast. Personally, I prefer the coast north of Portland (look into Boothbay Harbor), but you'll have to fly into Portland itself.

Quebec City is another excellent recommendation; it's an incredibly beautiful city, but I'm pretty sure you need a passport to fly to Canada.

Maine.

Great recommendations...thanks!

If we wanted to go West, perhaps NW, any recommendations there?