

Embarking on a journey from New Haven, CT to Tarrytown, NY is an exciting opportunity for any boater. This trip traverses a stretch of Long Island Sound before entering the Hudson River, providing scenic vistas, charming waterfront towns, and several opportunities for recreation and safe harbor. Designed with safety and pleasure in mind, this itinerary outlines essential navigation considerations, potential hazards, and delightful points of interest along your route.
1. Departure from New Haven, CT Begin your journey from New Haven Harbor, a busy waterfront facility catering to both recreational and commercial traffic. Before setting off, familiarize yourself with local conditions through reliable weather forecasts.
Here, New Haven Lighthouse serves as a prominent navigation aid on your departure, located near the harbor entrance (GPS: 41.2461° N, 72.8760° W). Ensure your charts and electronic navigation devices are up-to-date, and keep an eye out for tidal currents that can affect your departure.
2. Sailing towards Branford and Guilford As you navigate eastward, the coastline unfolds with opportunities for brief stops in Branford and Guilford. Both towns feature attractive harbors, friendly locals, and various dining options. In addition, these areas provide safe haven should weather conditions shift unexpectedly.
Watch for Faulkner's Island with its beautiful lighthouse and nature trails (GPS: 41.2526° N, 72.8160° W). It is a great spot to take pictures and stretch your legs.
3. Gradual Approach to Madison and Clinton Continuing northeast, the shoreline meets Madison and Clinton, known for their scenic beaches and charming downtown areas. The Clinton Harbor is well-equipped with docks and services for short stays.
A major navigational aid to note is the Clinton Lighthouse (GPS: 41.2883° N, 72.5098° W), which helps guide vessels into the harbor. Keep your electronic charting system updated, as this area can be busy with local bash boats, especially on weekends.
4. Passing through Long Island Sound Now headed toward Old Saybrook, your course will bring you through an open stretch of Long Island Sound. Be mindful of navigation aids like the Saybrook Breakwater Lighthouse (GPS: 41.2874° N, 72.3913° W). Monitor wind and wave conditions as they can become challenging in this area.
If poor weather arises, nearby Hammonasset Beach State Park can be an excellent spot for temporary anchorage, providing a safe and calm environment.
5. Rounding the Connecticut River As you near Old Saybrook, the Connecticut River appears, leading northwest toward the mouth of the Hudson. This is a significant point of interest due to its rich history and wildlife. Feel free to stop at marinas along the river if you desire a longer break.
Pay attention to any river traffic regulations, including no-wake zones and local fishing regulations, to ensure compliance.
6. Entering the Hudson River Upon entering the Hudson River, the scenery transitions beautifully. Look out for the Gilette Castle State Park on the opposite bank, which could inspire a future trip. As you approach Essex, the small towns along the coastline boast enjoyable dining options and small shops for stocking up on supplies.
As you approach Tarrytown, be prepared for drafting changes due to the rollicking river currents. Near Tarrytown Lighthouse, you'll find calming waters and safe berthing options, including marinas that can accommodate various sizes of vessels.
Be sure to admire the Hudson River’s beauty as you glide into Tarrytown. Make a stop to visit the Kirkland Museum or enjoy the historic downtown area filled with eateries, shops, and parks.
The new boater or experienced sailor alike will find this route engaging and manageable. While the journey features beautiful vistas and pleasant stops, maintaining vigilance regarding weather changes and other boaters is paramount. Always prioritize safety, respect local regulations, and be aware of changing conditions on the water.
This trip is not simply a route on a map; it's an experience woven with moments of serenity, adventure, and the joyful discoveries of waterfront life along one of America’s great waterways. Enjoy your voyage!