Steal My North Fork Itinerary for October

Hallockville Museum Farm’s Country Fair (Petite North Fork photo)

October always feels like a treat—from the crisp, cool weather to fall festivals (we see you, rescheduled Maritime Festival, now Oct. 16-18) to spooky season happenings. October is here, and there’s so much to do with kids across the North Fork. Let’s go!

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Having old-fashioned fun at Hallockville Museum Farm’s Country Fair, Riverhead

Hallockville Museum Farm’s 45th Annual Country Fair is scheduled for October 3 and 4 from 10 a.m. to 4 p.m. both days. This bucolic North Fork tradition features historical tours and traditional skills demonstrations, including colonial cooking over an open fire, broom making, and traditional bread baking; folk arts demonstrations including basket weaving, spinning, weaving, quilting, needlework, and wood carving; tractor pulls and parades; blacksmith, sawmill, and antique machinery demonstrations; wagon rides; and a children’s train ride with neighboring Long Island Antique Power Association. Our family’s favorite is always the old-fashioned children’s activities, including sack races, crafts, farm skills, and more. New this year will be a scarecrow-making contest, farm animal presentations by the Cornell Cooperative Extension of Suffolk County Farm, and a dress-up photo station featuring colonial costumes generously loaned to Hallockville by North Fork Community Theatre. Admission for the Country Fair costs $12/person for ages 12 and over, $8/child for ages 5-12, and free for those 4 and younger. This year, the Country Fair is offering half-priced admission on Sunday from 10 a.m. to 12 p.m. Tickets available at the door.

Getting spooky at the Long Island Aquarium Haunted Tree House, Riverhead

Five levels of spooky family-friendly fun await us at The Long Island Aquarium on Friday and Saturday evenings through October from 7 to 9 p.m., weather permitting. Best suited for children ages 3 to 11, the haunted tree house includes unlimited access to five levels of climbing, slides, and mazes. Admission to this Halloween excursion also includes an animal interaction, candy bags, pumpkin decorating, Halloween sand art, and crafts. The cost is $25/person; adult admission free with a paid child ticket; walk-ins are welcome, or purchase advance tickets here. Entrance to the Haunted Tree House is located behind the Hyatt Place Hotel, through Scoops Ice Cream Shop within Treasure Cove Resort Marina.

Learning about the Native Americans of Long Island at the Southold Indian Museum, Southold

Teaching my children (and learning alongside them) about the Native Americans who inhabited this land long before we did is an intentional, ongoing lesson. This month, we’ll visit the Southold Indian Museum to learn more about the culture and artifacts of the Algonquin tribe, including pottery, tools, children’s games and toys, and clothing. The museum is currently open on Sundays from 1:30 to 4:30 p.m. Admission costs $5/person. 

Hanging with prehistoric pals at Waterdrinker North Fork’s Dino Days, Riverhead

Giant animatronic dinosaurs have arrived at Waterdrinker North Fork! Head there through October 25 to check it out. Current hours for Dino Days are Monday through Friday from 10 a.m. to 6 p.m., and Saturdays and Sundays from 9 a.m. to 6 p.m. The cost is $20/person on weekdays and $28/person on weekends; admission is free for children two and under. In addition to seeing the dinos, admission also includes access to the pumpkin patch, hay ride, corn maze, mini golf, greenhouse, jump pads, and so much more fall fun. Purchase tickets in advance or at the door.

Supporting Gavyn’s Favorite 5K, Orient

When I heard the news about the devastating loss of beloved North Fork teen, Gavyn Drago, my heart broke, and I instantly felt helpless—probably like many of you. So when I saw that The Gavyn Avery Drago Foundation announced its Inaugural Gavyn’s Favorite 5K, I was eager to support Gavyn’s legacy by walking, running, and donating. The 5K will be held at one of Gavyn’s favorite places to run: Orient Beach State Park on Sunday, October 18. Learn more about the fundraising run and donate here.

Ice Skating and STEM-ing at a fun collab event, Calverton

On Sunday, October 3, from 1:30 to 3:30 p.m., Long Island Explorium is collaborating with Peconic Ice Rinks for an afternoon of ice skating and STEM. Families can enjoy a public skating session (with rentals included), hands-on STEM activities, and interactive experiments with Long Island Explorium educators designed to spark curiosity and encourage problem-solving. The cost is $25/person. Learn more here. 

Watching Hocus Pocus at a drive-in movie screening, Mattituck

Little beats the excitement of a drive-in movie. Pack up the kids and head to Strawberry Fields in Mattituck on Friday, October 9 at 6:30 p.m. for a screening of the Halloween classic, Hocus Pocus. This free event, presented by the Town of Southold Youth Bureau, also features treat bags for the first 50 guests, so head over early to snag your goodie bags and the best viewing spot. No RSVP required.

Enjoying fall festivities at Peconic Community School’s 3rd Annual Fall Harvest Festival, Cutchogue

A day of food, live music, farms, and so much fun for kids of all ages is what you’ll find at the 3rd Annual Fall Harvest Festival at Peconic Community School. This event, which is scheduled for Sunday, October 25, from 1 to 4 p.m. and open to all, is the perfect family-friendly way to spend a crisp fall Sunday. Admission is a $20/family suggested donation. Learn more here.

Choosing favorites at a Rock and Roll Car Show, Cutchogue

With a car-obsesssssssssed kid, there’s little chance we’ll be anywhere but at the Village Green in Cutchogue on Saturday, October 10, from 10 a.m. to 3 p.m. for the 2026 Rock and Roll Car Show. There we’ll be oohing and ahhing and choosing our favorites from tons of collectible cars in every vintage. We’ll also enjoy food, music, and raffles. The cost for admission is $5/person with proceeds funding the Mattituck-Cutchogue High School Youth Scholar Program for a paid internship. More info here. 

Picking pumpkins at Krupski Farms, Peconic

Last, but certainly not least, you’ll find our petite crew picking pumpkins and gourds (the funkier the better!) at fifth-generation family farm, Krupski Farms on Main Road in Peconic. This quintessential North Fork pumpkin farm is our pick for October fun, including pumpkin picking, a corn maze, a haunted barn, and a hay pit. Krupski Farms is currently open daily from 10 a.m. to 6 p.m.