Essex, Connecticut is a former ship-building harbor with a rich history. There are places that you can point to where one says that "The first Continental Navy war ship was built here," or "This is the oldest continuously operating inn in America," or (upon walking into that inn), "These are the muskets that were used to kick the British out of here in 1814". Today, there is a main street (called Main Street curiously enough) dotted with shops that make the area every bit as tony as Martha's Vineyard or Nantucket (without getting on a ferry). Essex also has the distinction of being "the best small town in America".
For paddling, the old harbor is separated into three distinct coves: North Cove, Middle Cove and South Cove. The paddling ranges between river conditions and bay or ocean conditions. One must pay attention to the tide as the current can run pretty strong on either the ebb or the flood. The wind must also bear some attention, there is always an island or two where one can find a leeward side.
This is also a yachting area. It should be said that one should be careful to look for boats coming out from between slips and that it would be seaman-like to remain to the outside of the channel and let the other boats that draw more water go by.
North Cove extends to the north of Essex Island and into Falls River. One can spend about 5 hours touring this area alone. Middle and South Coves (extending to the southerd of Essex Island, beyond the Connecticut River Museum, and down to Thatchbed Island) can buy you another four hours of paddling. At various times of the year, one can expect to see anything from geese and swans to eagles.
For wildlife observation, you will find that the Nature Conservancy is based right on Main Street.
Griswold Inn... the inn mentioned above. Numerous other B&B's and hotels in the area of Essex, Westbrook and Old Saybrook.
There are two free launch sites.
Follow either Interstate 95 or 91 to Route 9, get off at exit 3 and follow the signs into town.