Steal My North Fork Itinerary for September

Circus Splendiferous at Peconic Community School (Photo courtesy of Peconic Community School)

This month, as we trade beach bags for backpacks, we’re not letting the September blues get us down. Nope! Instead, we’re focusing on all there is to do on the North Fork with kids this month. From festivals to special events to time in nature, spend your September on the North Fork with us.

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Joining the circus (well, sort of!) at Peconic Community School’s Circus Splendiferous, Cutchogue

On Friday, September 18, at 5:30 p.m., Circus Splendiferous will return to Peconic Community School in Cutchogue for an evening of splendor. This event, which is open to all, will feature a 45-minute interactive outdoor circus performance followed by a 1-hour workshop experience for children where they’ll learn circus skills like juggling, spinning, and clowning from the circus performers. Tickets will be available at the gate with a suggested donation of $25/family, and don’t forget to bring your own seating — chairs, picnic blankets, you name it! 

Celebrating the North Fork’s maritime heritage at the 36th Annual Maritime Festival, Greenport

From the annual Merry Merfolk parade to the children’s activities in Mitchell Park, the Maritime Festival is always a big hit with our fam and friends. This year, the festival will take place on Saturday, September 26, and Sunday, September 27, from 9:30 a.m. until 5 p.m., with the parade on Saturday at 11 a.m. Visit the Greenport Maritime Festival website for the complete schedule of festival events.

Picking our weight in apples, North Fork

We’re not too proud to say that we are one of those fams who pick apples multiple times each September. Whether we’re bringing along friends from out of town or want a peaceful weekday filler for our own crew, we look forward to apple picking every year when the weather cools. As far as the spot, some of our favs have been Breeze Hill Farm, Harbes Orchard, and Woodside Orchard. Look for our Guide to North Fork Apple Picking hitting Petite North Fork this week. 

Sampling the best of the North Fork on the North Fork Foodie Tour

Picking a favorite North Fork fall event is no easy feat, but the annual Foodie Tour always tops our list. We’ve attended this event for over a decade, and while it was amazing before having kids, taking the kids along to some of the more family-friendly tour stops makes the experience even better. This year, the North Fork Foodie Tour, which celebrates 20 years,  will take place on Sunday, September 13, from 10 a.m. to 4 p.m. Tickets cost $35 per adult, free for children 12 and under. Purchase tickets and view the tour schedule here. 

Making self-portraits and sculptures with Artfully Long Island at Art Lab, Greenport

Art Lab led by Nicole Roccaro of Artfully Long Island invites artists of all ages, from tiny to teen, to create at their own pace using recycled and upcycled materials while enjoying the prettiest setting at Hotel Moraine. This month’s session will be held on Sunday, September 6, from 11:30 a.m. to 1 p.m. There, creators will make self-portraits and sculptures inspired by Alexander Calder. Tickets cost $15/person and can be purchased here. 

Going on a nature scavenger hunt with Group for the East End, Cutchogue

No matter the age, scavenger hunts are a big hit with everyone. Group for the East End will host a late summer nature scavenger hunt on the trails of Downs Farm Preserve on Saturday, September 5, from 10 to 11 a.m. There, we’ll search for natural treasures as we hike this special spot. Registration is required for this free event.

Taking a long walk down Narrow River Road, Orient

While this isn’t a set event, it’s become an annual happening for our family as summer turns to fall and the air begins to crisp. Toss your family’s scooters, bikes, whatever, into the car and head to Orient for a long stroll down Narrow River Road. We like to point out the different things we see and hear along the way and soak in the beauty that surrounds us. And the day isn’t complete without lunch from The Orient Country Store. Highly recommend this family outing.

Looking at the moon and stars (and more!) at Custer Observatory, Southold

Being unapologetically “Look at the moon” people, this evening is SO for us! On Saturday, September 19, at 6:30 p.m., we’ll celebrate “International Observe the Moon Night 2026” at Custer Institute in Southold. At this annual celebration, we’ll listen to live music and guest speakers as we view and learn about the moon and stargaze. This event costs $10 per adult and $5 for children under 16. Bring your own blankets and chairs. Learn more here. 

Learning how to hula hoop at KK’s the Farm, Southold

For something different and interactive, head to KK’s the Farm in Southold for Flow Arts Fridays where people of all ages can learn hoop instruction and more. The sessions kick off on Friday, September 4 at 3:30 p.m., then they will be hosted on Fridays in September at 5 p.m. Each session costs a suggested $20/person, though all are welcome regardless of the donation. You do not have to attend all sessions. These family-friendly sessions are open to all ages and abilities. Find the complete details here.

Building our own LEGO creations at Krafty Hands walk-in days, Riverhead

The notion that “other people’s toys are always more fun” fits just right for this one. At Krafty Hands, located in the Tanger Outlets in Riverhead, families can take advantage of their walk-in days and enjoy a two-hour LEGO building session for $20/child — perfect for a rainy fall day when you just need to get out of the house. No appointment needed. Check out Krafty Hands walk-in schedule here.