I’ve always taken physical fitness seriously, but this commitment was seriously tested at around 0200 hours during the first night of the 2004 Block Island Race. I was sailing with my dad and our crew aboard my dad’s modified J/44, Southern Cross, when we ran into some really funky, variable winds, I think somewhere off of New Haven.

Our watch captain and longtime friend Mike didn’t like the way that the number two headsail was flying (it wasn’t pretty), so we swapped to a gennaker, which also displayed poor posture. Then the wind perked up and clocked forward, so it was on to the number three headsail for maybe ten minutes before the wind speed abated and rotated aft, signaling that it was time to go back to the gennaker. Again.

This kept up for the next hour or two, with wind changes unfurling at the ragged end of the just-wait-and-see window. As the guy jumping halyards, I also found myself shedding layers almost as rapidly as we were shifting sail-change gears.

While time has dulled my exact sail-change count, it wasn’t an insignificant number.

The good news is that we kept our VMG up, but the less-than-great news was how utterly shot I was at the end of my watch, which was my first graveyard shift of that season (and before Voke tablets were invented). The wind eventually settled down and we were able to pressgang the number-three headsail for the entirety of my off-watch (those guys will suffer Karmic justice in the next life), but the experience taught me that even a “mini” distance race such as the 186-nautical miles that separate the Block Island Race’s starting line (off of Stamford, Connecticut) from its finishing line (also off of Stamford) can be more physically taxing than climbing a glaciated mountain.

While many crews use the Block Island Race (established 1946) as a warm-up for bigger offshore events such as the Newport Bermuda Race, the Marion Bermuda Race, or the Marblehead to Halifax Race, the course itself provides a great early season challenge and involves navigational conundrums including negotiating the eastern end of Long Island Sound, rounding Block Island, and then rewinding these miles back to Stamford.

Today, the Block Island Race, which starts on Friday, May 28, includes two courses: the 186 nautical mile Block Island Course that I’ve been fortunate enough to have sailed quite a few times, and the shorter, 125 nautical mile Plum Island Course, which also begins off of Stamford and rounds the red and white whistle (Plum Island) to starboard.

This year marks the race’s diamond anniversary, and a glance at the entry list includes boats as diverse as an Express 37, several J/44s (but sadly not my dad’s), a handful of J/111s, J/121s and J/122s, and a Morris 51, not to mention sportboats such as a Melges 20.

I checked in with Ray Redniss, vice commodore of the Storm Trysail Club, via email, to learn more about the diamond anniversary of this classic mini distance race.

What kind of entry numbers are you seeing this year? Also, how do these stack up to previous editions of the regatta?

The initial numbers have been very encouraging since we opened registration. As of May 1st we have 50 entries. As of that date in 2019 we had 40, and in 2018 we had 46. I’d say we’re pretty consistent.

Weather-wise, what kind conditions can sailors expect to encounter on Long Island Sound in late May? Also, what are the best-case and worst-case weather scenarios?

Great question for which there is the gamut of answers! Pretty much anything but snow!!

We have had benign drifters and white-knuckle screamers! From the sublime to the ridiculous!

The best case would be a beautifully steady 12 to 15 knots out of the southwest, which would give us great points of sail around the course.

Worst case would be a toss-up…either not enough air to move a feather, or 30-40 knots from the east!

How important do you think local knowledge will be for this now-classic distance race? Also, if you could offer one piece of advice to visiting (and local) teams, what would it be?

As with any race of this nature, local knowledge can play an important role.

Understanding how the winds behave between the North Shore of Long Island and the South Shore of Connecticut/Rhode Island under the different weather patterns is key right out of the gate.

[The race’s] first order of business is getting out of [Long Island] Sound. Then, you are faced with the decisions of determining the best way to exit… The Gut? The Race? Little Gull? The Sluice? Even Fisher’s Island Sound!!

I’d say the first piece of advice is to be ready for anything. Have all safety gear in tip-top condition and [make sure that] all crew know where it is and how to use it.

[My] next piece [of advice] would be to study the weather predictions, the current charts, and develop a game plan…have a strategy.

What kinds of safe-play pandemic tactics are you and the other regatta organizers planning?

Interesting phrase…”pandemic tactics!” That game has been continually changing.

You can’t design a strategy, so all you have are tactics!! The nice thing about a distance race without a pre-race get-together is just that – you don’t have to put a bunch of people together!

Building on that last question, will you be able to have any shoreside events to celebrate the race’s proud 75th anniversary?

We will have a Thursday afternoon/evening and Friday morning pick-up for YB trackers, and we are planning on an outdoor awards party on Sunday.

[The State of] Connecticut anticipates opening without restrictions by mid-May. I certainly hope conditions allow that to happen!

When you consider the different racecourses, what do you see as the trickiest bits of water to get right from a strategy and tactics perspective? The Race? Plum Gut?

Yes! The Race, The Gut, Little Gull…even Fisher’s Island Sound! The trick is to get out of the Sound with the least amount of adverse current.

I know it’s still early days in terms of entries, but are your eyeing any perennial favorites for strong finishes? What about any dark horses?

Good question! So far, we don’t seem to have any of the big boats entered.

What we do have is a bunch of great teams with some potentially tight rating bands! In looking at early finishers, I’d say we need to watch Temptation-Oakcliff, Christopher Dragon XI, Pterodactyl [and] the Oakcliff Farr 40’s, each of [which] have been among the early finishers in past events.

Can you tell us about any efforts that you and the other regatta organizers have made to try to lower the regatta’s environmental footprint or otherwise green-up the regatta?

This event has always been fairly environmentally sensitive. We usually don’t provide more than the signal boat and a photography boat, although we occasionally have a safety boat to keep spectators from crowding the start line and being in the way of competitors.

That mostly happens when the wind is more northerly and port tack is favored after the start. We have had some very close calls! But in general, the process of running this event is not a fuel or otherwise environmentally-intense effort.

Anything else that you’d like to add, for the record?

This is my 25th year as race committee for the event. I started out in 1994 working with Peter “Luigi” Reggio, who handed it over to me as chair in 1996. Last year would have been my 25th and last as chair and PRO, but COVID delayed that departure to this year.

On behalf of the event, I’d like to thank Stamford Yacht Club for their years of excellent hospitality. I am honored to continue to serve our sport, and thank Storm Trysail for offering me the opportunity.

by David Schmidt