Summer Comedy Show
Chris Plumer headlines stand-up at SquareHead Brewing Company, which means you can pair craft beer with actual laughs instead of just pretending bar conversation counts as comedy. The Holbrook brewery's been hosting comedy nights that actually land, and their food menu holds up beyond typical bar snacks. Show starts at 7:30 PM, so you've got time to grab dinner there first.
Chris Plumer headlines stand-up at SquareHead Brewing Company, which means you can pair craft beer with actual laughs instead of just pretending bar conversation counts as comedy. The Holbrook brewery’s been hosting comedy nights that actually land, and their food menu holds up beyond typical bar snacks. Show starts at 7:30 PM, so you’ve got time to grab dinner there first.
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Other Arts events
Editor's Pick Bay Street Theater — Summer Mainstage Opening Night
Sag Harbor's beloved 299-seat regional theater opens its 2026 summer mainstage season. Premiere-night audience, celebrity sightings, real theatrical ambition. Plan dinner at Tutto Il Giorno or American Hotel — both walkable, both reserve weeks ahead in July.
- When
- Where
- Bay Street Theater, Sag Harbor
- Price
- See ticket page
Editor's Pick Community Crit Night at Studio Kash with Syd Glasser
Syd Glasser hosts a free critique night for Long Island artists who work solo and want feedback in a low-pressure setting. Bring work in progress to Kasher Gallery in Northport—it's a chance to talk through what you're making with other people who actually get it.
- When
- Where
- Kasher Gallery & Studios, Northport
Editor's Pick Kasher Gallery & Studios Anniversary Celebration
Studio Kash is marking one year on Scudder Avenue with an open house—free drinks, snacks, and a chance to see the gallery and studio spaces. It's a casual Sunday afternoon thing, good for meeting the people behind the workshops and checking out the spot if you haven't been yet.
- When
- Where
- 19 Scudder Ave, Northport
Read before you go
- town spotlight Sayville Village: A Local's Guide for 2026 Sayville Village — the South Shore walkable downtown that locals refuse to gentrify, with restored 19th-century Main Street, the Sayville Cab Company since 1958, the Sayville Restaurant Group anchors (Casa Luis, Cull House), the Saturday Farmers Market on Foster Avenue, the Fire Island ferry terminal at the harbor, and an annual event calendar that runs from Memorial Weekend Classic Car Show through Holiday Stroll. Walking distance from the LIRR. The slow-paced South Shore village that works.
- town spotlight Northport Village: A Local's Guide for 2026 Northport Village — the North Shore harbor village with restored 19th-century Main Street, the working harbor + town park, the Engeman Theater, the Saturday farmers market, and the John W. Engeman Theatre + Northport Yacht Club rituals that anchor the village's calendar. Walking distance from the LIRR. The North Shore family Saturday at its best.
- town spotlight Babylon Village: A Local's Guide for 2026 The complete local's guide to Babylon Village — the South Shore's underrated harbor village. Argyle Theater, Argyle Lake, the restaurant strip, Fire Island ferry access, and the off-hours moves locals know.