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

Things to Do in Islip This Weekend

This weekend in Islip (May 30 to 31): 26th Annual Islip Street Fair at Main Street (Sunday 11:00AM); Fleetwood Macked: The Ultimate Tribute to Fleetwood Mac at CM Performing Arts (Saturday 7:30PM).

Events for the weekend of May 30 to 31, 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 Islip this weekend.

This Weekend's Top Picks

This Weekend's Top Picks in Islip: 26th Annual Islip Street Fair at Main Street (Sunday 11:00AM); Fleetwood Macked: The Ultimate Tribute to Fleetwood Mac at CM Performing Arts (Saturday 7:30PM).

26th Annual Islip Street Fair

Sunday, May 31, 11:00AM  |  Main Street, Islip  |  Free

Islip's biggest street party of the year takes over Main Street with vendors, food, and live entertainment all afternoon.

Fleetwood Macked: The Ultimate Tribute to Fleetwood Mac

Saturday, May 30, 7:30PM  |  CM Performing Arts, Oakdale

(from the website: For over 16 years Fleetwood Macked the Ultimate Tribute to Fleetwood Mac has been enchanting audiences across the US and now Europe. Selling out 85% of ticketed shows in 2024 and hailed as the most authentic Fleetwood Mac tribute band in the U.S., much of the realism comes from the band’s history. Husband and wife musical team Hillary and Michael (Stevie and Lindsey ) and friends Caroline, Jay, Phil and Andrew (Christine, John and Mick), that have made great music together in various incarnations finally all came together with their mutual love of Fleetwood Mac. All the members of Fleetwood Macked are and have always been professional, touring Rock musicians, which also adds to the authenticity of the sound of the band. Fleetwood Macked live brings the passion, depth, heart and the musicianship Fleetwood Mac’s music requires. Whether performing the Rumours album in its entirety or a decade’s show featuring Fleetwood Mac’s hits from the 70’s, 80’s, 90’s and today, every performance transports audiences to another time and place. Complete with costume changes, dialogue and video backdrops it is a show not to be missed.

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