City Island Yacht Club

Incorporated 1907

Big Tom Wednesday Night Series


Big Tom Yacht Racing’s name stems from a pesky rock named “Big Tom” at the northeast corner of Eastchester Bay near the shore of City Island. This rock has snared far too many unsuspecting sailboats. It is near the location for the starting mark for our events.

City Island YC along with our partnered neighboring club, the Harlem YC, established Big Tom Yacht Racing in 2020 in an effort to revive yacht racing on Eastchester Bay. For a variety of reasons, participation under the prior organization had been dwindling. Our new organization stressed simple, friendly, fun, inclusive racing. In our inaugural year, despite the Covid pandemic, participation in our Big Tom events increased dramatically as compared to recent years.

Big Tom Yacht Racing administers the following two events that can be accessed via the links:

Additional information for both events can be found at and below. 

Big Tom Events:


The Big Tom Wednesday Night Series (BTWNS) is administered by City Island Yacht Club. This series is a new version of a long tradition of fun Wednesday Night “Beer Can” Racing on Eastchester Bay that goes back over 40 years.

The BTWNS is designed to be a welcoming, fun and inclusive event attractive to both experienced competitors and novice racers alike. It features interesting windward-leeward and triangular/courses, low number of races to qualify, multiple throw-outs and a low series cost.  

The BTWNS is a weekly event consisting of sixteen (16) scheduled races held every Wednesday from19 May 2021 through 01 September 2021 for PHRF Spinnaker, PHRF Non-Spinnaker and One Design Divisions (minimum of 5 boats) divisions.

The first start is scheduled for 7pm each week and races are usually done by about 9 pm so skippers and crews can get some essential “post race” food and drink and meet and greet their competitors back at the yacht club restaurant and bar.

Big Tom Wednesday Night Racing is managed on Yachtscoring’s web site. This is the leading web site for management of yacht racing events. Registration and payment may be made on this web site. The Notice of Race and Sailing Instructions are also posted here as are general announcements and results.

Big Tom Racing Skippers’ Meeting – May 12, 2021

After a great inaugural season, Big Tom is back! Learn more about this successful Wednesday night series and the plan for ...
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BIG TOM CITY ISLAND CUP – JUNE 12 and 13, 2021

BIG TOM CITY ISLAND CUP – Saturday and Sunday JUNE 12 and 13, 2021 This regatta is administered by our partnered ...
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Big Tom Yacht Racing News

Commodore’s Update (July 3, 2020)

Dear Friends, This weekend, the weather is expected to be exceptionally fine. Celebrate July 4th with expanded al fresco dining ...
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Big Tom Yacht Racing is the New Version of a Classic Weeknight Sailboat Racing Event…

At the westernmost end of Long Island Sound, the Big Tom Wednesday Night Series offers 16 weekly sizzling summer evening ...
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