Yes it does, we (those doing this route frequently) usually leave it down to traverse Lake Champlain and have it raised again in Sorel where the Richelieu flows into the St-Lawrence. Depending on your eventual destination you may wish to go from Waterford to Oswego, on the Erie-Oswego canal, raise the mast, cruise lake Ontario, the Thousand islands (NY and Ontario), sail down-river to Montreal, Québec City or even the Saguenay fjord (see the belugas) turn back to Sorel, lower the mast, go to Waterford through the Richelieu, lake Champlain and the NYS Canal. That's a lot of cruising! From the Chesapeake I'd say 2 to 3 months...
I'm just back in the St-Lawrence at 45°10'N, 074°20'W (if you Google, the boat is at 45.159661,-74.336032) after spending the last nine months cruising the US east coast, the Bahamas and back up the east coast.
Whatever your destination, remember that the cruise starts the day you leave; it's not the destination it's the whole trip.