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Log 31: Conley Reunion in Stratford / Milford

Updated: Mar 15, 2023

Crew Log for October 6th, 2022


Trip Summary:

  • Thimble Islands to Stratford / Milford, Connecticut

  • Trip Distance of 24.4 NM, Total Distance To-Date of 1,067.9 NM

  • Departed at 0900 hours and arrived at 1430 hours

  • Trip Tracks


It was a beautiful sunny day and a bit warmer than it has been for the past week or so. We had a nice 5 – 8 knot breeze out of the north to move us down the Connecticut side of Long Island Sound to Milford, which is directly across the Housatonic River from Stratford. You’re unlikely to see this as a stop on many cruisers trip logs to the Bahamas, but we had an important reason for making the effort.


One of the things we were most looking forward to during this trip, was to be able to reconnect with family and friends. At the risk of speaking for Judy (a mistake I’ve made too many times in the past), while we enjoy each others company most of the time, it is a treat to have other special people come into our lives, even if it is only briefly. A welcomed change of scenery so to speak.


My cousin Jane, aka Liz as she’s know in these parts, is a nurse in Stratford and, well, that was the perfect excuse to chart a route down the Connecticut coastline. Fortunately for us, Jane was also off work the day we arrived.


We had a restful night on anchor at the Thimble Islands. It was so peaceful and still that you won’t know you were on a boat, which was in sharp contrast to what we had heard about the conditions, given the lack of protection from most wind directions. As we prepped the boat for our departure, Judy took some beautiful shots of the locals (birds). If you haven’t seen them, go back to the previous post and have a look.


There is a really strong tidal current in Long Island Sound. If you plan your trip right, you get a boost of 1.5 – 2 knots, but of course, you have the current against you if your timing isn’t right. We wanted to arrive in Milford by early afternoon to give us time to explore since we were only there for an overnight. The wind the following day was forecasted to be perfect to cross the Sound to Long Island and so our visit with Jane would be brief.



Stratford / Milford, are a long way the Housatonic River. We arrived on an outgoing tide and so in addition to fighting powerboat wakes, we had to contend with a 2.5 knot current, which made for some slow progress up the river. Our route took us by some beautiful salt marshes, which were home to numerous birds, including some beautiful white swans. A little further up the river we went by hundreds of boats on moorings at the local yacht clubs and marinas. The conditions and activity in the river required attention from both if us, so we apologize for the lack of pictures.



On the recommendation of one of the members at the North Cove Yacht Club back in Old Saybrook, we were staying at the Dockside Marina, which was literally right next to the Dockside Brewery and Restaurant on the Milford side of the river. We did however have to request a bridge opening for the Hamilton St. Bridge, which was undergoing repairs at the time. The Bridge Master asked as to hoover 100 yards from the bridge to give them time to move equipment and the workers off the bridge. After a short wait, they opened one side of the bridge and we made our way through to Dockside.


The Dockside Marina is bordered by Hamilton St to the south and I95 and the railway line to the north. Tying up here was a sharp contrast to the quiet, stillness we left at the Thimble Islands. However, it was a nice change to be "on a dock" where we could simply step off the boat without getting into the dinghy and where we could refill our water tanks, easily.



After a smooth docking, we made our way on foot across the bridge to Stratford to the West Marine. I was browsing around the store when I heard Judy talking to someone. To my surprise, my cousin Jane found us in West Marine after I had texted her and told her we had arrived.


After a quick visit to Elizabeth M, we went “up river” to Ayer’s Landing Marina, which is operated by Jane’s good friend Ned and his brother. Oh the stories these guys could tell! Ned’s marina is on the Housatonic River, in Shelton. Our trip took us by the hospital that Jane works in, which was directly across from the Sikorsky Helicopter facility. From there we made our way back to Stratford to Jane’s house and her beautiful property. It was obvious that she acquired Aunt Janice’s green thumb.



Ned and Jane treated us to a delicious meal at the Bridge House, across the street from the Dockside Marina. It was a perfect afternoon and evening in Stratford / Milford and a real treat not only to reconnect with my cousin Jane, but to meet Ned, who’s company we really enjoyed. My only regret was that we enjoyed the evening so much, none of us had thought to take a picture.


Tomorrow we would be heading due south, across Long Island Sound to Port Jefferson. The trip across was expected to be 15 miles or so and would be one of our shorter travel days While we were excited to get to Long Island, our trip seemed boring compared to one Ned took several years before. Ned, who loved fast cars on a quarter mile (hence his lack of hearing) and vintage motor bikes, also used to water ski. He told us a story of him water skiing from Stratford to “Port Jeff” one sunny afternoon. I still smile when I reflect back on some of Ned’s stories.


It was so nice to reconnect with family and we are really happy we got to Stratford. Unfortunately, our trip back down the Housatonic doesn’t go nearly as smoothly as our trip up. It was without a doubt, a real shit show.


But, more about that, next time.


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