Festivals, Fairs & Family Fun

🌻 North Fork Family Guide (Sept 11–19, 2025)

Here are the special events, organized by date, with where and when so you can plan easily.

🗓 Thursday, September 11

• 8th Annual Scarecrow Contest – Entry Week
  • Where: The Shoppes at East Wind, 5768 Route 25A, Wading River
  • When: Entry period runs until Friday, Sept 19 (setup by Sept 24; voting starts Sept 27).
  • Details: Families can design and register their own scarecrow. Great craft project for kids; plus the Shoppes have a carousel, candy shop, and family dining.
• Cruise Night Car Show
  • Where: The Shoppes at East Wind, Wading River
  • When: Wednesday, Sept 11 | 5–9 PM
  • Details: Classic cars, music, food trucks, and a carnival-like feel—fun for kids who love shiny vehicles.

🗓 Saturday, September 13

• Fall Native Plant Sale
  • Where: Roy Latham Nature Center, Inlet Pond County Park, Greenport
  • When: 9 AM – 1 PM (also runs Sunday, Sept 14)
  • Details: Buy and learn about native plants. Great excuse to walk the trails with kids and explore the park.
• Fall Garden & Meadow Tour (ReWild North Fork)
  • Where: Self-guided, with sites in Cutchogue, Southold, Greenport, East Marion; one site at Custer Preserve, 1115 Main Bayview Rd, Southold
  • When: 10 AM – 1 PM (rain date Sept 14)
  • Details: Free tour of gardens and meadows. Kid-friendly outdoor exploration; bring walking shoes and snacks.
• Rock ‘n Roll Car Show
  • Where: Cutchogue Village Green
  • When: 10 AM – 4 PM
  • Details: Vintage cars, food vendors, raffles, DJ music. Great for kids who love cars and for a lively family day outdoors.
• Peeko Oysters Tour (for families with older kids)
  • Where: Southold (Peeko Oysters farm)
  • When: 2 PM
  • Details: Learn about oysters, aquaculture, and the bay. Adults can taste oysters; kids can enjoy the water and hands-on learning.
• One-Act Theatre Festival
  • Where: Corchaug Repertory Theatre (likely in Southold/Cutchogue area)
  • When: 7 PM (also runs Sept 14)
  • Details: Short plays. Best for older kids/teens interested in drama.

🗓 Sunday, September 14

• Fall Native Plant Sale (Day 2)
  • Same details as Saturday, Sept 13.
• Garden & Meadow Tour (Rain Date)
  • Same details as Sept 13.
• Relaxing Sunday at Sannino Vineyard
  • Where: Sannino Vineyard, Cutchogue
  • When: 1–4 PM
  • Details: While wine is the focus, the vineyard is kid-friendly outdoors with open space and live music.
• Brunch a la Mexicana at RGNY Winery
  • Where: RGNY Winery, Riverhead
  • When: 11 AM
  • Details: Outdoor brunch with live music. Some wineries provide lawn games and open lawns that kids enjoy.
• One-Act Theatre Festival (Day 2)
  • Same details as Sept 13.

🗓 Thursday & Friday, September 18–19

• Burger Nights at McCall Wines
  • Where: McCall Wines, Cutchogue
  • When: Thursday, Sept 18 & Friday, Sept 19 | 4 PM
  • Details: Grass-fed beef burgers, fries, chocolate treats. Family-friendly—kids can enjoy food and outdoor space while parents sip wine.
• Sannino Vineyard After Hours (older kids/teens only)
  • Where: Sannino Vineyard, Cutchogue
  • When: Friday, Sept 19 | 8–11 PM
  • Details: Live music, cocktails, nightlife vibe—not ideal for younger children.

🎠 Ongoing Family Activities (Any Day, Sept 11–19)

• Mitchell Park Carousel – Greenport; classic ride overlooking the harbor.
• East End Seaport Museum – Greenport; lighthouse and maritime exhibits.
• Farm Stands & U-Pick – Wickham’s Fruit Farm (Cutchogue), Harbes Family Farm (Mattituck) often have apple picking, pumpkin patches, corn mazes, hayrides starting mid-September.
• Nature Walks – Hallock State Park Preserve (Riverhead) and Orient Beach State Park are great for family hikes and picnics.

🗺️ Quick-Glance Family Schedule