FRIDAY
Friday Night Flights | Corey Creek Tap Room, 45470 Main Road, Southold, 631-765-4168
Enjoy live music from Haig Mathosian from 4-8 p.m. with food available from Roadhouse Pizza Truck. Bring friends and enjoy an evening of music, food and drinks. For more information, click here.
First Fridays on Love Lane | Love Lane, Mattituck
Spend 6-9 p.m. eating, drinking and exploring Love Lane for an evening of family fun as the street closes to traffic. Shops will stay open late, with food, local craft beverages and artisanal goods available to enjoy. This will be the final event of the season. For more information, click here.
Create Your Harvest Blend | RGNY, 6025 Sound Ave., Riverhead, 631-298-0075
Create a custom red blend using estate petit verdot, cabernet sauvignon, cabernet franc and merlot while learning about the art of winemaking. The 90-minute experience includes a guided blending session with a wine ambassador and artisanal snacks, followed by time to bottle a personalized blend; sessions are available throughout the day. Cost is $96 per person. To learn more and to book, go here.
SATURDAY
Country Fair | Hallockville Museum Farm, 6038 Sound Ave., Riverhead, 631-298-5292
Celebrate local agriculture, history and community traditions with family-friendly activities including colonial cooking and traditional craft demonstrations, farm animals, children’s games, Indigenous presentations, local vendors, wagon and kiddie train rides, tractor pulls, live music, food and produce, honey and jam competitions from 10 a.m.-4 p.m. A scarecrow-making competition will also be featured. Admission is $12 for adults, $8 for children ages 5 to 12 and free for children age 4 and younger. The fair will also be held Oct. 4, with half-price admission offered that morning only. For more information, click here.
The Great Pumpkin Palooza | Lenny Bruno Farms, 740 Wading River Road, Manorville, 631-591-3592
Celebrate fall with a full day of pumpkin picking, hayrides, a corn maze and seasonal farm activities, from 11 a.m.-5 p.m. Browse local vendors, enjoy food trucks and autumn treats, and listen to live music while the family takes part in activities such as bounce houses, face painting, fairy hair, permanent jewelry and henna. Beer and wine will be available from Westhampton Beach Brewery, along with special guests, spooky photo opportunities and plenty of fall fun. This event will also be held Oct. 4. Entry is $10; an educational hayride around the farm is $5. For more details, go here.
Witches & Wizards Paddle on the Peconic | Peconic Riverfront, Downtown Riverhead, 631-727-5744
Celebrate Halloween early on the Peconic River with a festive paddle parade featuring witches, wizards and spooky-season enthusiasts in costume from 3-3:30 p.m. Participants can decorate their kayaks, canoes and paddleboards and paddle along Riverhead’s scenic waterfront, while spectators line the Riverwalk and Riverfront for photos and fun. Participants are required to wear a Personal Flotation Device and a whistle for safety, as per the police department. To RSVP and to learn more, go here.
Hampton Vintage Market | Mattituck Historical Society, 18500 Main Road, Mattituck, 631-298-5248
A curated selection of vintage fashion, rare designer finds, handmade goods and independent designers will be on display from 10 a.m.-5 p.m. with free admission and plenty of treasures to discover. For more information, look here.
Deadwood & Friends | Treiber Farms, 38320 County Road 48, Peconic, 516-425-1458
The Grateful Dead tribute band takes the stage at 5 p.m. for an evening of live music, dancing and good vibes. The eight-piece band will perform a unique set list, accompanied by animated visuals and a full light show inside the barn. Admission is $20. Guests are welcome to bring their own beverages and lawn chairs, and food trucks will be on-site. The band will also perform Oct. 4. To purchase tickets and for more information, click here.
SUNDAY
Sculpture @ Sylvester Manor: [R]evolution Guided Tour | 80 North Ferry Road, Shelter Island, 631-749-0626
Explore an outdoor collection of sculptures and installations with curator Tom Cugliani during a guided walk through the historic grounds from 10-11:30 a.m. The free tour features work by a range of East End artists and requires advance registration; recommended for ages 10 and older. Participants should wear comfortable shoes and be prepared for wooded paths and uneven terrain; tick repellent is recommended. The tour is not ADA-accessible. Park in the public lot near the restrooms and meet at the front door of the Manor House. For more information, go here.
Chowderfest | Port Waterfront Bar & Grill, 104 3rd St., Greenport, 631-333-2501
Chowderfest returns from 12-4 p.m., bringing North Fork restaurants together to compete for top chowder honors. Tickets are $35 online or $45 at the door, with proceeds benefiting the East End Seaport Museum and Marine Foundation. For tickets and more information, look here.
We Are Live Fall Fest | Greenport Harbor Brewing Co., 42155 Main Road, Peconic, 631-477-1100
Enjoy a day of fall festivities featuring local vendors, food trucks, live DJs, a cornhole tournament and a golf simulator from noon-6 p.m. The first 200 attendees will receive giveaway bags. Admission is $25 and includes activities and, for guests 21 and older, a first beer. The event also supports the Nick Singh Foundation. For tickets and additional information, go here.
27th Annual Fall Festival | Cooperage Inn, 2218 Sound Ave., Baiting Hollow, 631-727-8994
From 1-5 p.m., gather outdoors for a family-friendly fall celebration with live music by Slingshot, local food, hot spiked cider and craft beer. Admission is free, with food and drinks available for purchase. For more details, click here.
