THURSDAY
The 5th Annual Northforker Wine & Food Classic, Borghese Vineyards, 17150 Middle Road, Cutchogue
The weather calls for clear skies tonight, making for a perfect evening of dozens of local food, wine and fun by vines at Northforker’s 5th Annual Wine & Food Classic. Join us at 7 p.m. (6 p.m. if you’re feeling VIP!) for this delicious North Fork tradition — and ultimate way to kick off Labor Day Weekend! Grab your tickets here.
Poetry in the Greenspace | Mattituck-Laurel Library, 13900 Main Road, Mattituck, 631-298-4134
At 4 p.m., enjoy readings from the co-founders of Poetry Street, Susan G. Dingle and Robert A. “Bubbie” Brown, and other local poets; bring an original poem or one to share, or just come to listen. Free; registration encouraged here.
Trivia Night | Greenport Harbor Brewery, 42155 Main Road, Peconic, 631-477-1100
Test your trivia knowledge with head brewer Sean Galligan from 6-8 p.m. in the Peconic tasting room for a chance to win a $25 gift certificate. More information can be found here.
G.E. Smith & the American Blues with Special Guest Samantha Fish | Suffolk Theater, 118 East Main St., Riverhead, 631-727-4343
Former Saturday Night Live house bandleader and renowned guitarist G.E. Smith and The American Blues series is back, and this time with special guest guitarist and singer-songwriter from Kansas City, Missouri, Samantha Fish, from 8-10 p.m. Tickets are $80-$120. For tickets, click here.
FRIDAY
Live Music & Wood-Fired Pizza | Jamesport Vineyards, 1216 Main Road, NY-25, Jamesport, 631-722-5256
From 6-8 p.m., enjoy live music by New York City-based guitarist and vocalist Julian Love and wood-fired pizza paired with your favorite Jamesport wines. Menu prices apply; reservations are recommended. This event is 21 and over. For more information and reservations, visit here.
First Fridays on Love Lane | Love Lane, Mattituck
It’s the second to last First Friday, so bring the family to stroll, shop, eat, drink and listen to music from New York City-based singer, guitarist and songwriter Greg Humphreys at this popular monthly event sponsored by the Mattituck Chamber of Commerce. From 6-9 p.m.; free. For more information, click here.
Hellenic Film Festival | North Fork Arts Center, 211 Front St., Greenport, 631-477-8600
Fans of Ted Lasso won’t want to miss this underdog documentary screening of King Otto from 7-9 p.m. The story focuses on the 2004 phoenix-from-the-ashes rise of the national football team of Greece, a country that had never previously won a single match or even scored a goal in a major tournament, and how they took down the giants of world football to become the unlikeliest of European Champions. Tickets are $30 and are available for purchase here.
SATURDAY
Greenport Boy Scouts Fall Craft Fair | Greenport School Grounds, 720 Front St., Greenport, 631-477-1950
From 10 a.m.-4 p.m., check out this craft fair with over 60 vendors, live music, food trucks and artisanal foods benefiting the Greenport Boy Scouts; rain date Sept. 6. Free admission and parking; for more info, look here.
Live Music: Illusion | Pindar Vineyards, 37645 Main Road, NY-25, Peconic, 631-734-6200
Cover band Illusion, who play the songs of female rockers from the ‘60s to the ‘90s (think Stevie Nicks, Joan Jett and Sheryl Crow) is back at Pindar for a live musical performance from 1:30-5:30 p.m.; free. For more details click here.
Everything Makes Sense | Custer Institute and Observatory, 1115 Main Bayview Road, Southold, 631-765-2626
Beginning at 8:30 p.m., ambient duo Worst Night Ever presents an immersive multimedia live performance under the stars, with guided telescope tours to follow the performance. Tickets are free for children under 16, $28.52 for general admission and $23.18 for observatory members. For more information and to reserve tickets, click here.
SUNDAY
Freestyle Night | Transfiguration of Christ Church, 1950 Breakwater Road, Mattituck, 631-298-9652
From 5-10 p.m., enjoy freestyle hits with DJ Boosted along with food, wine and beer. Tickets are $40 per person, $45 at the door; one drink free with entry ticket. For details, look here.
Balourdet Quartet | Shelter Island Friends of Music, Shelter Island Presbyterian Church, 32 N Ferry Rd., Shelter Island, 631-749-0805
At 6 p.m., Shelter Island Friends of Music continues its 2026 season with a free concert by the award-winning Balourdet Quartet, who will perform works by Ravel and Brahms. A reception with the artists will follow the performance; free. For more information, click here.
Foodie Fest | Tanger Outlets, 1770 W Main St., Riverhead, 631-369-2732
From 12-7 p.m., this event features East End bites from top vendors, gourmet treats, food trucks and festival favorites as well as family-friendly entertainment and activities. This event is free and occurs on Saturday and Monday at the same time as well. For details, look here.
