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

Things to Do in Sayville This Weekend

This weekend in Sayville (August 27 to 30): Saturday Sounds with Paris Ray featuring food by Orchard Street at Loughlin Vineyard (Saturday 12:00PM); Pizza Night at Loughlin's with Chef Clemente at Loughlin Vineyard (Friday 4:00PM); "Recreate a Masterpiece" Exhibit & Photo Contest at Long Island Maritime Museum (Thursday 10:00AM), plus 5 more picks below.

Events for the weekend of August 27 to 30, 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: Saturday Sounds with Paris Ray featuring food by Orchard Street at Loughlin Vineyard (Saturday 12:00PM).

Also Happening This Weekend

Also Happening This Weekend in Sayville: Pizza Night at Loughlin's with Chef Clemente at Loughlin Vineyard (Friday 4:00PM); "Recreate a Masterpiece" Exhibit & Photo Contest at Long Island Maritime Museum (Thursday 10:00AM); Sunday Sounds with Julian Love and Food by Orchard Street at Loughlin Vineyard (Sunday 12:00PM).

Pizza Night at Loughlin's with Chef Clemente

Friday, August 28, 4:00PM  |  Loughlin Vineyard, Sayville

Wood-fired pies with live music by Sippin' On a Sound; walk-ins welcome. Held out of Date Night for the Loughlin de-stack.

"Recreate a Masterpiece" Exhibit & Photo Contest

Thursday, August 27, 10:00AM  |  Long Island Maritime Museum, West Sayville

A creative exhibit and photo contest at the Maritime Museum; not listed on the museum's own site, aggregator source only.

Paint and Sip with Palmette

Thursday, August 27, 5:00PM  |  Loughlin Vineyard, Sayville

A guided paint-and-sip evening in the vineyard.

Red Rue Express

Saturday, August 29, 4:00PM  |  Sayville Theater

A live show at the Sayville Theater.

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