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

Things to Do in Bay Shore This Weekend

This weekend in Bay Shore (May 15 to 17): Shakedown Citi: Throwing Stones Tour at Boulton Center for the Performing Arts (Friday 7:00PM); Island Symphony Orchestra Young Performers Competition Concert at St. Peter's by-the-Sea Episcopal Church (Sunday 2:00PM); Paint & Sip - Red, White & Paint Night at Fire Island Vines (Friday 6:00PM), plus 2 more picks below.

Events for the weekend of May 15 to 17, 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 Bay Shore this weekend.

This Weekend's Top Picks

This Weekend's Top Picks in Bay Shore: Shakedown Citi: Throwing Stones Tour at Boulton Center for the Performing Arts (Friday 7:00PM).

Shakedown Citi: Throwing Stones Tour

Friday, May 15, 7:00PM  |  Boulton Center for the Performing Arts, Bay Shore

The Grateful Dead tribute act returns to Boulton with their full-band Throwing Stones Tour for a night of extended jams and deep cuts.

For Families

For Families in Bay Shore this weekend: Island Symphony Orchestra Young Performers Competition Concert at St. Peter's by-the-Sea Episcopal Church (Sunday 2:00PM).

Island Symphony Orchestra Young Performers Competition Concert

Sunday, May 17, 2:00PM  |  St. Peter's by-the-Sea Episcopal Church, Bay Shore

The next generation of South Shore musicians takes the stage at a stunning Bay Shore church for an afternoon of classical music that families and music lovers will both treasure.

Date Night & Nightlife

Date Night & Nightlife in Bay Shore this weekend: Paint & Sip - Red, White & Paint Night at Fire Island Vines (Friday 6:00PM).

Paint & Sip - Red, White & Paint Night

Friday, May 15, 6:00PM  |  Fire Island Vines, Bay Shore  |  $$

Fire Island Vines pairs guided painting with their tasting-room atmosphere for a relaxed, creative Friday night with someone you like.

Free & Affordable

Free & Affordable in Bay Shore this weekend: Sounds of Silence 5K Run/Walk and 10K Run at Walker Beach (Saturday 8:00AM).

Sounds of Silence 5K Run/Walk and 10K Run

Saturday, May 16, 8:00AM  |  Walker Beach, Brightwaters  |  $$

A waterfront Brightwaters 5K/10K supporting hearing-loss awareness, a strong morning option for runners and walkers.

Also Happening This Weekend

Also Happening This Weekend in Bay Shore: Bingo Brunch at Tula Kitchen (Sunday 11:00AM).

Bingo Brunch at Tula Kitchen

Sunday, May 17, 11:00AM  |  Tula Kitchen, Bay Shore

A Sunday brunch bingo session at one of Bay Shore's standout kitchens.

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