Unbelievable New England Fall Cruising Weather

The last two times we have done this October trip down Long Island Sound, we were battered by freezing temps and constant northwest gales. This year it is an entirely different game.

October 13 – 14, 2021
Stonington, CT, Milford, CT and City Island, NY
Days #2 & #3

What an outstanding trip down Long Island Sound we have had. Two picture perfect days, with runs of 55 miles and 42 miles. Flat water, sunshine (mostly), dry and clear. Mornings have been perfectly crisp, afternoons relatively warm, and evenings simply pleasant. Such a change from our previous trips, which were characterized by ice on the decks, three-day gales that pinned us down on both sides of the Sound, and making mad dashes from one port to another — any port that was safe — during the brief lulls in the nasty weather. We were braced for it again this year, but we need not have worried.

We have also enjoyed consistent running at slow trawler speeds. While we can go 15 to 19 knots if we need to (and we did, regularly, in previous years), it is refreshingly pleasant to cruise along in flat water at eight knots. The boat is steady, the engine is quiet, and the scenery is lovely. I can prepare yummy snacks in the galley. We can relax without hanging on. The boat is dry and clean. In addition, there are few other vessels to cause wake and to require constant focus. We are rested. We could get used to this.

Esmeralde is comfortable living space under way in these prime conditions.
Wednesday October 13

Our stay at Dodson’s in Stonington was typically serene. We departed at a leisurely hour in glassy calm, weaving our way through the lovely fleet of classic yachts in the mooring field. As usual, we didn’t know where we were going, except that we were going west.

We contemplated Port Jefferson on the Long Island side, as well as Milford and Bridgeport on the Connecticut shore. All are different. The only one we had visited before was Port Jefferson, on our first trip south three years ago when we were pinned down for three days in a northwest gale. (It’s not the place to be in a northwest gale, by the way, but we survived.)

We tossed the question of destination out to Bruce’s Facebook group, Trawler Life. The response that came back was unanimous: Milford. I had heard nice things about the town, so Milford it was.

The skies got a little threatening for an hour or so mid-afternoon, caused by a small disturbance moving overhead. We had no rain and just a little breeze around 10 – 11 knots out of the south, which caused us no pain. By the time we approached the entrance to the river at Milford, conditions were back to calm and mostly sunny. It was a pleasant ride up to the the town landing. The river is jam-packed with boats, but few were moving.

We tied up in our slip and did a brief clean-up, as we had taken almost no spray and everything was quite tidy, above and below. Another plus to quiet weather. Jim the harbor master welcomed us and gave us a few tips about visiting town.

We took the pups for a walk to reconnoiter. While we had several dinner recommendations in hand, we ultimately elected to go to the simplest option, Flipside Burgers, right across from the town dock. We did not have high expectations, but it was easy, simple, and they welcomed our pups with open arms. Ultimately we had a great supper. Bruce pronounced his patty melt “The best I’ve ever had,” and I had a terrific arugula and white bean salad — even the beans were home-cooked and tasty. Perfect choice.

Esmeralde lies alongside the town landing in Milford, CT.

Back on the boat, Bruce was inspired to pop open one of our bottles of home-made Arancello for a quick night-cap. It was quite pleasant sitting in the pilot house on a quiet evening, looking across at the town recreation area of Wilcox Park.

We enjoyed a little home made Arancello for a nightcap in the pilot house.
Thursday, October 14

The next morning dawned just as the last: a lovely weather forecast and a relatively easy run of 45 miles. My little furry four-footed alarm clocks went off as usual. They are incredibly reliable. Between 6:00 and 6:10 am the little gentle whimpers start. Our efforts to train them to a square of astroturf have paid off. I carted them up to the cockpit, where they both performed the required tasks on cue. Be still my heart. I could stay in my bathrobe and slippers.

After coffee and breakfast, I walked the pups and Bruce waxed the transom (boats will be boats, after all), and we were off the dock by 9:10. Bright sunshine, a gentle north breeze. Perfect conditions for another day on the sound.

We needed to get ourselves as close to the East River as possible so we could catch the early current through the river and Hell’s Gate. That pointed us to Port Washington, NY or City Island, NY. Both very different destinations. I was leaning towards City Island because it has a storied past in the sailing world, and I had never been there. But as the day before, we tossed it out to our Trawler Life peeps. The feedback was split. We opted for City Island.

The day proceeded much as the day before. The Sound remained incredibly calm and beautiful. The northerly hovered around 10 knots and there were few other boats around. Traffic increased as we pressed west, but travel remained easy and relaxing.

The best moment of the day was getting a call on channel 13 from a the tug Fort Point, with a tow. I panicked because I thought I had screwed something up, but it was a friendly hail from the captain asking “are you the Esmeralde from the Facebook group Trawler Life?” What a hoot! He’s a tugboat captain by day, and has his own tug for private use after hours. What fun!

The tug Fort Point hailed us on channel 13 asking if we were the Esmeralde from the Facebook group “Trawler Life”. Yes we were!

We passed Port Washington. New York City rose above the horizon in the sparkling afternoon sun, and we turned south of Hart Island in towards City Island. We hailed Minneford Marina and were guided into an easy slip alongside.

Once settled and showered, we hooked up the pups and went for a walk. While I knew City Island was part of The Bronx, I was surprised when we turned onto the main drag that it really felt like “The Bronx”. I don’t know what I was expecting, exactly, but I had this sense of City Island as an historic sailing Mecca, a focal point for traditional boatbuilding and sailmaking. There’s not much of that visible anymore, aside from a few murals along the sidewalks.

However, we wandered around and found a small local restaurant, The Black Whale, that allowed us to sit with our dogs at a sidewalk table for dinner. It was incredibly warm for an October evening: we ate in our shirt sleeves. We had a very pleasant dinner with surprisingly good food. The locals wandering by paused to chat, especially with the puppies, which gave the whole experience a friendly neighborhood feel.

Our appetizer at The Black Whale was grilled shrimp with guacamole. It must be a thing around here: we had never heard of it before, but we had it last night at the burger joint in Milford also.

The next few days will be a dance with the weather. We will be up in the morning at O-dark-hundred and will catch the early current down the East River along Manhattan. This is always an exciting ride and we are looking forward to it. We’ll then pass through New York Harbor, under the Verrazano Narrows Bridge, and on to New Jersey. If the southerly hesitates, we will push down the shore to Manasquan and duck inside. That will give us options as the weather deteriorates. We can run inside the New Jersey ICW, or we can run outside, or we can sit tight. We like options.

Here is a video of our departure from Milford Landing, and down through Milford Harbor to the breakwaters.

16 thoughts on “Unbelievable New England Fall Cruising Weather”

  1. Love hearing your updates again! happy cruising to you guys and the pups! One quick question if you have time, Do you use any weather service for planning ever? I know you mostly only go when when conditions are right, but from time to time a little help is nice on tricky passages. Thanks and Take Care!

    Liked by 2 people

    1. Hi Roger, We do not use any weather service for planning. I do refer to several resources. First and foremost is NOAA. Then there are all the various apps, depending on exactly what I am trying to figure out. Windy, PredictWind, SailFlow, WindFinder Plus and RadarScope, plus buoy reports, are all in my quiver. If we were to be doing a lot of offshore passages I might look into a routing service, but for our current coastal cruising I find it is not necessary.


  2. We were up in Barnegat Bay yesterday sailing north past Tices when we saw this trawler and wondered if it was you. We’re enjoying following your new journey! Nancy and Chris

    “Be joyful in hope, patient in affliction, faithful in prayer.” Romans 12:12


    Liked by 1 person

    1. Hi Nancy and Chris, Yes, that was us! So funny you recognized us! We had a lovely day yesterday, and visited with friends las night at Silver Cloud on the Forked River. Had a wet and blustery, but not too difficult, run to Atlantic City today. On to Cape May tomorrow, where I will hopefully have a chance to update the blog. Thanks for saying hi!


      1. We’re at Rick’s Marina on Forked River. We must have still been out sailing when you passed our Marina going up the river. I took a picture of your boat passing by us in the opposite direction on the bay. Not a great picture but enough to identify it was you 😁 Did you go out Barnegat Inlet or Manasquan?

        Liked by 1 person

      2. Actually from Forked River we went south, and stayed inside the ICW all the way to Atlantic City. With the southerlies yesterday (and with two puppies on board) we didn’t really want to go outside and bash into it. We were fine inside, although there were three places in the marsh at Great Bay where it got really skinny. Today we ran outside in the WNW breeze from AC to Cape May. We stayed close into the beach, and it was fine. Sorry we missed you at Forked River! It’s a great spot, and we’ll definitely be back!


      3. Funny, I thought I answered this but now I can’t find it so I’ll try again. We actually stayed inside all the way to Atlantic City. It was just too windy out of the south to go outside, especially with the puppies. We found some skinny spots, but we were OK. I wouldn’t want to do it with a lot more draft than we have, and I would never do it with exposed props or pods. We’re in Cape May now, waiting for the north westerlies to calm down so we can run up the Delaware.


  3. Hi guys, glad you have finally been able to throttle back and enjoy the passage. The weather Gods have certainly been with you for this portion of the trip. Hallelujah! You have quite a support group as well.
    Looking forward to all the good times aboard with you all, it brings back so many great memories
    Dean and Kathy

    Liked by 1 person

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