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

Things to Do in Sayville This Weekend

This weekend in Sayville (September 10 to 13): Backroads BBQ & Wine Down at Loughlin Vineyard (Friday 3:00PM); Fall Kickoff Weekend: Saturday Edition at Loughlin Vineyard (Saturday 12:00PM); Fall Kickoff Weekend: Sunday Edition at Loughlin Vineyard (Sunday 12:00PM), plus 3 more picks below.

Events for the weekend of September 10 to 13, 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: Backroads BBQ & Wine Down at Loughlin Vineyard (Friday 3:00PM).

Backroads BBQ & Wine Down

Friday, September 11, 3:00PM  |  Loughlin Vineyard, Sayville  |  Free

Chris Devine plays live from 4:30 to 7:30 while Crossroadsque works the smoker and the wine and beer flow into the evening on the farm.

Also Happening This Weekend

Also Happening This Weekend in Sayville: Fall Kickoff Weekend: Saturday Edition at Loughlin Vineyard (Saturday 12:00PM); Fall Kickoff Weekend: Sunday Edition at Loughlin Vineyard (Sunday 12:00PM); Trivia Night at the Vineyard Hosted by Tango Time at Loughlin Vineyard (Thursday 6:00PM).

Fall Kickoff Weekend: Saturday Edition

Saturday, September 12, 12:00PM  |  Loughlin Vineyard, Sayville

Orchard Street cooks a fall menu all day and Rodehauss plays 2 to 5 at the vineyard.

Fall Kickoff Weekend: Sunday Edition

Sunday, September 13, 12:00PM  |  Loughlin Vineyard, Sayville

Orchard Street and Tall Mutha Shucka oysters all day, with live music 2 to 5 at the vineyard.

Bottles & Bloom Workshop

Thursday, September 10, 5:00PM  |  Loughlin Vineyard, Sayville

A hands-on floral-and-wine workshop for a relaxed Thursday evening.

Mahjong at the Vineyard

Thursday, September 10, 5:00PM  |  Loughlin Vineyard, Sayville

A social mahjong session at the vineyard.

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