FRIDAY
Friday Night Music with Julian Love | Rooted North Vineyards, 13050 Oregon Road, Cutchogue, 631-734-1100
Kick off the weekend with live music by local musician Julian Love from 5-7 p.m. Enjoy wines by the glass or bottle alongside seasonal food specials in the tasting room. Weather permitting, music will take place outdoors on the terrace near the firepits; otherwise, the performance will move indoors. Reservations are recommended. For more information, click here.
Artist Showcase featuring Mike Meehan | Bridge Lane Wine, 35 Cox Neck Road, Mattituck, 631-298-1942
Meet local artist Mike Meehan during an evening of art and wine from 5-7 p.m. Explore his oil and watercolor paintings inspired by the landscapes and waterscapes of Long Island’s North and South Forks while enjoying a glass of wine. His artwork will remain on display through Dec. 20. More details are available here.
Absolute Adele with Jennifer Cella | The Suffolk, 118 East Main St., Riverhead, 631-727-4343
Enjoy an evening of Adele’s biggest hits performed by vocalist Jennifer Cella, best known for her work as a lead vocalist with the multi-platinum group Trans-Siberian Orchestra. Accompanied by a group of musicians, Cella recreates the sound of the Grammy-winning singer in a live tribute performance beginning at 8 p.m. Tickets are $40-$80. For tickets and additional information, go here.
SATURDAY
Riverhead Pumpkin Smash | Riverhead Yard Waste Facility, 532 Youngs Ave., Baiting Hollow
Give Halloween pumpkins one last hurrah at the Town of Riverhead’s free, family-friendly pumpkin-smashing event from 11 a.m.-3 p.m. Bring your jack-o’-lanterns and pumpkins to smash with a large mallet, toss or watch as heavy equipment crushes them. All pumpkins will be composted on site (please remove candles, paint and plastic decorations before bringing pumpkins). The event is open to all ages and will take place rain or shine. For more information, click here.
PAUMANOK 2025 Barrel Tasting | Paumanok Vineyards, 1074 Main Road, Aquebogue, 631-722-8800
Get an inside look at the winemaking process with winemaker Kareem Massoud during an intimate tasting in Paumanok’s barrel cellar. Sample 2025 red wines, including malbec, merlot, cabernet sauvignon, cabernet franc and petit verdot, directly from the barrel. The experience also includes barrel-fermented chardonnay and late-harvest sauvignon blanc served from the bottle, accompanied by cheeses, breads and pâté. Tastings are offered at 1 and 4 p.m. Tickets are $50 per person, with the tasting fee credited toward the purchase of 2025 vintage futures. Reservations are required. Email [email protected] for reservations. For additional details, go here.
SUNDAY
Contemporary Art Quilts Exhibition and Sale | Unitarian Universalists of Southold Gallery, 51900 Main Road, Southold, 631-765-3494
Spend an afternoon exploring contemporary quiltmaking and textile artwork by Mary Richards. The exhibition and sale run 1-5 p.m., offering visitors an opportunity to view the artist’s work. For additional information, call 631-765-3494.
The Chaotic Hypnotic Game Show | The Suffolk, 118 East Main St., Riverhead, 631-727-4343
Get ready for an interactive evening combining live stage hypnosis with the excitement of a television game show. Hosted by master hypnotist Tim Miller, alongside Michelle Miller and featured guest comedians, the 90-minute production invites audience members to participate in the action, either from their seats or onstage. Participation is voluntary, and guests must be 18 or older to participate onstage. Doors open at 6 p.m., with the show beginning at 7 p.m. Tickets are $40-$70. To learn more and to purchase tickets, click here.
