THURSDAY
Booked & Reserved: Book Discussion Group | Kontokosta Winery, 825 North Road, Greenport, 631-477-6977
From 3-4 p.m., take your love of books on the road for an afternoon of conversation, wine and North Fork scenery. The Cutchogue-New Suffolk Free Library will launch its first traveling book discussion with a look at The Anthony Bourdain Reader: New, Classic, and Rediscovered Writing by Anthony Bourdain. Jul Fedele, a Wine & Spirit Education Trust Diploma candidate known from the library’s wine tastings, will lead the discussion and share her knowledge on wine while participants explore the connections among food, travel, culture and literature. Registration is required. To learn more, go here.
“From Settlement to Hamlet: Stories of Cutchogue’s Colonial Past” | Cutchogue-New Suffolk Library, 27550 Main Road, Cutchogue, 631-734-6360
The Cutchogue Civic Association will host an evening exploring the community’s colonial-era roots 5-6:30 p.m. Mark MacNish of the Cutchogue-New Suffolk Historical Council and the local history librarian, Mariella Ostroski, will discuss the people, places and stories that shaped the area’s development from an early settlement into a hamlet. The program is free and open to the public. For more details, go here.
Thursday Night Bingo | American Legion Post 803, 51655 Main Road, Southold, 631-765-2276
Doors open at 6 p.m., with bingo kicking off at 7 p.m. Come ready for an evening of fun, friendly competition and the chance to take home cash prizes, with payouts based on attendance and sales. Everyone is welcome. Bring along your favorite food and nonalcoholic drinks, but remember to bring cash, as it’s the only form of payment accepted. The bar will be closed. For more information, click here.
FRIDAY
Chris Devine | Twin Fork Beer Co, 807 Raynor Ave., Riverhead, 631-209-4233
Enjoy an evening of live acoustic country music with Long Island singer-songwriter Chris Devine from 6-9 p.m. Grab a craft beer, relax with friends and enjoy live music. For more information, go here.
Friday Night Flights | Corey Creek Tap Room, 45470 Main Road, Southold, 631-765-4168
From 4-8 p.m., enjoy live music by George Tebbit alongside food and treats from Roadhouse Pizza Truck, Barbara’s Sweet Treats and North Fork Big Oysters. A longtime musician, Tebbit got his start after being inspired by The Beatles, eventually performing with Long Island rock band Good Rats and later taking part in projects including Tuesday Afternoon, Beyond Fab and Sir Paul. Today, he performs solo at vineyards, restaurants, weddings and private events, covering a wide range of musical styles. For details, click here.
The Smithereens | The Suffolk, 118 E Main St., Riverhead, 631-727-4343
At 8 p.m., The Smithereens will bring their rock ’n’ roll sound to the stage with special guest vocalist Marshall Crenshaw. Formed in New Jersey in 1980, the band has spent more than four decades building a following with its energetic performances, guitar-driven songs and melodic hooks. With 17 albums and more than 2,500 live shows, the group continues to carry on the musical legacy of founding frontman Pat DiNizio, who died in 2017. Tickets are $60-$90. To purchase tickets and to learn more, go here.
SATURDAY
Autumn Antiques, Fine Art, & Crafts Fair | Southold Historical Museum Maple Lane Campus, 55200 Main Road, Southold, 631-765-5500
From 9 a.m.-5 p.m., Browse antiques, fine art, pottery, photography, handmade crafts and vintage treasures from a variety of vendors. Live music will add to the atmosphere as visitors shop and explore the vendors. Presented with the Old Town Arts and Crafts Guild, the fair offers something for collectors, shoppers and art lovers alike. Admission is $5 for adults and includes a free raffle ticket. The fair will also be held Sunday. For more details, look here.
Riverhead Fire Department Open House | Riverhead Fire Department, 540 Roanoke Ave., Riverhead, 631-727-2751
Bring the whole family for a fun and educational day at the firehouse from 1-4 p.m. Explore fire trucks up close, watch live demonstrations, learn important fire-safety tips and enjoy activities for children. Meet local firefighters and emergency-service personnel while enjoying complimentary refreshments. The event is free and open to the public. A rain date is set for Sept. 27.
Jeff LeBlanc | Terra Vite North Fork Winery & Vineyard, 250 Manor Ln., Jamesport, 631-722-3416
From 1:30-4:30 p.m., enjoy an afternoon of live music with singer-songwriter Jeff LeBlanc. Known for his blend of soulful, acoustic-driven music, LeBlanc has performed alongside artists including Chris Stapleton, Tori Kelly and Michael McDonald. Relax, enjoy the music and take in the vineyard setting. Reservations are strongly recommended. For more information and to make a reservation, go here.
SUNDAY
Wading River-Shoreham Chamber of Commerce Fall Festival | The Shoppes at East Wind, 5768 Rt. 25-A, Wading River, 631-929-3500
From 11 a.m.-5 p.m., enjoy a free day of fall fun featuring live music by SouthBound, line dancing, food trucks and local vendors. Kids can bounce, create and play with a variety of crafts and activities while adults browse local goods and enjoy the community atmosphere. Admission is free and the event will be held rain or shine. For more, look here.
Chloe Halpin | Riverhead Ciderhouse, 2711 Sound Ave., Baiting Hollow, 631-591-0217
Enjoy live music from 2-5 p.m. surrounded by the cider tasting room. Chloe Halpin will perform a selection of original songs blending singer-songwriter, country and pop influences, with music exploring themes of life experiences, relationships, faith, adventure and connection with others. For more details, go here.
