South Shore Digest Long Island's South Shore, curated weekly

Things to Do in Sayville This Weekend

This weekend in Sayville (May 22 to 24): Corks & Claws: Saturday Edition at Loughlin Vineyard (Saturday 12:00PM); Corks & Claws: Sunday Edition at Loughlin Vineyard (Sunday 12:00PM); The Oyster Sessions featuring Loughlin Vineyard (Friday 4:00PM).

Events for the weekend of May 22 to 24, 2026

Every week we read through everything happening across the South Shore and keep only what is actually worth your time. Here is what is on in Sayville this weekend.

Date Night & Nightlife

Date Night & Nightlife in Sayville this weekend: Corks & Claws: Saturday Edition at Loughlin Vineyard (Saturday 12:00PM).

Corks & Claws: Saturday Edition

Saturday, May 23, 12:00PM  |  Loughlin Vineyard, Sayville

A laid-back vineyard afternoon with live music from 2–5 PM and a steamed crab boil — bring a blanket and stake out a spot on the lawn.

Also Happening This Weekend

Also Happening This Weekend in Sayville: Corks & Claws: Sunday Edition at Loughlin Vineyard (Sunday 12:00PM); The Oyster Sessions featuring Loughlin Vineyard (Friday 4:00PM).

Corks & Claws: Sunday Edition

Sunday, May 24, 12:00PM  |  Loughlin Vineyard, Sayville

The Sunday version of Loughlin's vineyard crab boil with live music.

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