There's a whole world to explore just between Stonington and Mt. Desert, all that is covered in the Taft Guide...
Beyond Schoodic, however, things change pretty dramatically - considerably fewer boats venture further east. I love the area out around Jonesport - Mistake Island, the Mud Hole, the Cows Yard, and of course Roque Island are all beautiful anchorages with great exploring ashore...
The area out around Cutler and Eastport is pretty cool, I really enjoyed hanging out in Eastport for a couple of days... That town is barely hanging on, much of the main street was boarded up, but nevertheless I found it very welcoming and friendly, and the enterprising efforts of the locals to keep it alive inspirational. One of the best Mexican cantinas I've ever found anywhere was in Eastport, go figure...
Crossing Fundy to NS can be pretty ambitious at times, and even with a month in hand, that could be pushing it a bit... I'd suggest you give some thought to staying on the west side, and cruising Passamaquoddy Bay and perhaps the St John River, instead... I loved the town of St Andrews, and a trip through the Reversing Falls and up the St John can be every bit the adventure that sailing across to NS could be... You'll do plenty of motoring in there, to be sure, but it's a wonderful area to explore, and plenty of sailing opportunities if you're willing to make the effort, and be patient...
Not to mention, after some time along the chillier and perhaps foggier coast, the inland warmth of the rivers and lakes of the St John basin offer a real treat... A wonderful and unique cruising ground, highly recommended...