For our final Regatta Spotlight, we are heading to the Connecticut Coast for the Indian Harbor Yacht Club Classic Yacht Regatta. This stop in the Classic Yacht Challenge Series is a stunning early fall regatta, taking place in Long Island Sound in mid-September. To give us a sneak peak at what's to come later this year, CYOA spoke with Chris Foley:

What is the history and tradition behind this regatta, and how does it influence the experience for participants?

Chris Foley: For the past 13 years, our IHYC Classic Yacht Regatta has flooded Great Captain Harbor with the gorgeous classics, both large and small. Surrounded by some of the old classic boat builders from City Island up the Connecticut Coast, many members and neighbors have painstakingly kept these boats in pristine condition.

Often, one of our long-time launch drivers and local Greenwich legend, Frank, will regale stories he heard from his own father of the classic commuters and yachts from the Roaring 20s that graced the waterfront. That history comes alive as everyone from Cat Boats to a J Class drop their moorings and head out to the race course, up the channel and passing Todds Point in a beautiful parade of wood masts and cloth sails.

Much of the passion behind the event is driven by Lars Forsberg who, with his family, have cared for Alden design Spirit for decades, while also being big part of the Black Watch rehabilitation.

What sets the fleet of classic yachts at your regatta apart from other similar events? Are there specific types of yachts or notable vessels that regularly participate?

CF: We’ve been blessed in a number of ways. Ticonderoga of Greenwich, Spirit, Ranger, Delta House and Golden-Eye are long time loyal participants in The Classic. And we’ve also really embraced one designs that have long histories on the Long Island Sound, like the Shields Class as well as an original IOD Ibis. We hope that extends to the Atlantic class this year and helps create interesting, fresh regatta ideas for such historic classes. And with the local 12 Metre building history, it’s always phenomenal to see the 12 Metre that’s in our harbor, as well Columbia and the America IIs battle for glory.

Not to be forgotten, Cat Boats and the Cat Boat Association also are near and dear to our organization. With several in harbor, it’s of the few events in the area where we see them come out in droves to the starting line.

Additionally, while not a sail boat, spectators have ventured out on classic Trumpies and refurbished Lobster Boats with their beautiful New England water lines.

It’s beautiful to see the passion these shepherds of classic yachts bring, as well as the generational family and teams that clearly put so much love and attention into these yachts.

There aren't too many times in a boats career when a Hinkley Pilot 35 doesn't mind getting rolled by Ranger or Sophie.

What is special at your event to celebrate the classic yacht racing community during the event?

CF: A few years ago, we noticed that boats were making some pretty long hauls to get down the Sound. Coordinating with Sea Cliff who hosts the weekend prior, we also decided to make this a 2 day event. That two day event brings town folk to the edge of the local beach to see the parade, or even just down to the town docks to get a glimpse of these classics.

But that also means the dock party is a 3 day fanfare, with our welcome evening followed by Day 1 Awards/Banquet and then Day 2 Awards.

What’s also unique is that it’s the last of the CYOA Series. Often we hear from crews and owners of the vessels that they are so stoked for our party as they let their hair down and celebrate the end of a great CYOA Series. On Saturday Night, everyone gets out on the dance floor!

What aspects of your regatta make it a must-attend event for sailors and enthusiasts—whether it’s the location, race format, social atmosphere, or something else?

CF: We try to offer something to all with this event. Between the pure beauty of the dock walk alongside our historic club house, we also offer the pursuit start for the larger classics, a “round the islands” for Cat Boats and a one-design circle for those eager for windward leewards. It’s a big undertaking, but that only means a bigger party after with more tales to tell at the Sunfish Bar.

And what’s more, we’re always so thankful at the generosity of many owners who welcome the public onto their boats… and even offer wine, cheese or a beer from their local breweries.

Members who own more modern boats get in on the action too, driving their classic MGs and other iconic autos to park them on the waterfront overlooking the docks.

How does your regatta engage the wider community, and are there unique activities or events that connect spectators and non-sailors with the world of classic yachts?

CF: While the club is private, we try our best to open our doors through dock walks and even a sail! Our Junior program is open to the public, and we host several of the local High School sailing teams in town, all of which come down to the docks over the weekend to enjoy the experience.

Similarly, a local hotel, The Delmar, owned by a descendant of the historic sailing family, Mallory, creates experiences for guests to see the starts and finishes of the different race circles. When we say it takes over Captain Harbor, the view of the event from land looks like a city of boats!

The first regattas of the 2025 Classic Yacht Challenge Series are just around the corner! Sign up today to make sure you're part of all the action!