Boating The Housatonic and Long Island Sound

Captain Frank on his Boston Whaler in Long Island Sound
The Housatonic channels waters from The Berkshire Mountains in Massachusetts to Stratford CT where it empties into Long Island Sound. The waters are navigable from The Sound upstream to Derby CT. On a choppy day - take refuge in the deep and silky fresh river waters in Fairfield County.

It was Memorial Day in 2012 and there were forecasts for a drenching. But, my friend still wanted to show me boating New England style. In case the storms ever materialized we decided to stay close to the launch point in Stratford.  There was plenty of great boating to be had in this area.

Frank has a Boston Whaler of his own; he has also had the pleasure of commanding yachts of all sizes - from the Gulf of Mexico to Long Island Sound - so i was in capable hands.

Our first jaunt was over to Milford harbor, then over to the protected side of Charles Island. Along the way we saw many crabbing spikes - seemingly a hazard to me who was not used to having random spikes poking out of the water.  We set the anchor and had a lunch by Charles Island and watched as teenagers got trapped out on the island by high tide - which was very entertaining.  (See my article on Charles Island for an explanation).  After lunch we cruised back to Stratford and headed up The Housatonic.

Wooster Island, The Housatonic, Connecticut
Wooster Island, The Housatonic, Connecticut
The River was bursting with recreational spirit. There were many jet skies, fishermen, swimmers, and other boaters out for a cruise.

We passed by Wooster Island where many other small boats were anchored.  The island has excellent beaches, a few trails and camping sites, and good swimming for kids.  There was a very fun-loving flotilla holding the West side of the Island. Further up-stream we came to Derby CT where the river splits and becomes difficult to navigate. We turned around and found a swimming hole.  It was a very pleasant day, we spent about 5 hours boating.

One thing to note: Hurricane Irene sent plenty of trees into the river and they are mostly submerged.  These obstacles will be lodged in place for years to come - though they might not be visible from the surface.  So, before you break out the water skies, check out the area for debris.


Address for your GPs: 1 Beacon Point Rd, Stratford, CT


Stratford Boat Launch
Coastal Access Guide


Washington Bridge, Housatonic River, Connecticut
Washington Bridge, Housatonic River, Connecticut