Steal My North Fork Itinerary for May
Welcome to the month of May! If you’re looking for a month jam-packed with family-friendly events, May is your girl. From street festivals to celebrations and shows, you’ll find it all and more on the North Fork this month. See you and your petite crew there!
Steal My Itinerary is made possible by Mariah Mills, your local Real Estate Advisor — helping families buy, sell, and rent homes across the North Fork.
Kicking off the First Fridays season, Mattituck
What a way to welcome the month of May! Our favorite in-season event series is back on Friday, May 1, from 6 to 9 p.m. on Love Lane, and will feature the soulful sounds of Bubba Jam. First Fridays is a monthly family-friendly event that welcomes you and your crew to eat, drink, dance to live music, shop, and play in a block-party hangout. First Fridays are free to attend and open to all.
Watching school buses (and more!) race at Riverhead Raceway, Riverhead
The action returns this month at Riverhead Raceway! On Saturday, May 16, our fam will be in the stands cheering on all of the evening’s races, including one of our very own petite crew members competing in the juicebox race. The evening will conclude with the excitement of watching the school buses take on the figure 8 course. Grandstands open at 5 p.m. with opening ceremonies at 6:30 p.m. Admission, which is cash only and available at the gate, costs $30/adult, $20/child ages 6-12, and is free for children 5 and under. Ear protection is highly suggested. Learn more here.
Climbing Horton Point Lighthouse, Southold
After successfully climbing the Fire Island Lighthouse with the kids this winter, we were eager to take our courage to the North Fork. Horton Point Lighthouse reopens for the season MDW, and will be open Saturdays and Sundays from 11:30 a.m. to 4 p.m. throughout the summer. An inside tour will give you a look into the lives of former lighthouse keepers and staff, and a climb to the top, which features 27 circular steps to the top, plus seven steps to the watch tower and another seven to the lantern, presents sweeping views of the lighthouse grounds and the Long Island Sound. Admission to the lighthouse is $10/family, cash only. More info here.
Celebrating the almighty dandelion at the Dandelion Festival, Southold
Celebrate the almighty dandelion at this annual event that always leaves a lasting impression on our family. On Sunday, May 3, from 11 a.m. to 5 p.m. at KK’s Farm in Southold, gather for a day of farm tours, educational workshops and discussions, live music by Brady Rymer, Points East, and others, hula hooping, kids’ crafts, animal encounters, and more. This event is free to attend. Park in dedicated lots or on the south side of Main Road; no parking is allowed on the north side.
Seeing Greenport through a camera obscura, Greenport
Greenport’s camera obscura — one of about 50 public camera obscuras left in the world — gives you a view of Greenport as you’ve never seen before. Perfect for a game of eye-spy, a camera obscura reflects a live, 360-degree, two-dimensional image of the outside onto a viewing table. This is made possible by the reflection of light from mirrors on top of the building, filtered through a small pinhole, then projected onto the viewing table. Greenport’s camera obscura is open to the public on Saturdays and Sundays from 10 a.m. to 12 p.m., with donation-based admission. Learn more here.
Watching the street come alive at East End Art’s 30th Annual Mosaic Street Painting Festival, Riverhead
Prepare to watch Main Street in downtown Riverhead transform into the most colorful and vibrant street you’ve ever seen. On Sunday, May 31, from noon to 5 p.m., during this free, family-friendly event,East End Arts and the local community will create mosaic-style street art using chalk for all to enjoy. There will also be live music, dance and theatre performances, a drum circle, children’s activities, local food trucks, and more to enjoy. And, don’t forget to swing by the “Kid Zone” with your petite crew.
Cheering on the tractor pulls and checking out the hit and miss engines at Long Island Antique Power Association’s Spring Show and Plow Day, Riverhead
The annual spring show day at Long Island Antique Power Association is always on our list, and not just because we have a vehicle-obsessed kid. The day features tons of family fun for all, from watching the tractor pulls to hay and barrel train rides, to learning about hit and miss engines, and watching blacksmith and sawmill demonstrations. This year’s show is scheduled for Saturday, May 30, and Sunday, May 31, from 10 a.m. to 4 p.m. The cost is $10/adult and is free for children under 12 and veterans.
Creating record collages and weaving projects at Art Lab at Hotel Moraine, Greenport
Make Art Lab a part of your MDW! Art Lab at Hotel Moraine, 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. The May session is planned for Sunday, the 24th, from 1:30 to 3 p.m. Tickets cost $15/person and can be purchased here. This month’s session will feature collaging on upcycled records and weaving projects using various materials.
Attending a “fin-tastic” birthday party for Long Island Aquarium’s Jimbo, Riverhead
The Long Island Aquarium is throwing a birthday bash in the waterfront Sea Star Ballroom for everyone’s favorite shark: Jimbo! This family-friendly party, which is set for Sunday, May 17, with bookings at 11 a.m. and 2 p.m., will feature a kid-friendly buffet, a mascot parade with performances, DJ entertainment, Jimbo’s birthday cake presentation, complete with a group Happy Birthday song, photo opportunities, and more. Admission to the party also includes admission to the aquarium for a visit before or after the party. The cost is $59.95 for adults ages 13+, $39.95 for children ages 3-12, and $10.35 for children under 2. Member discount available. Book here.
Meeting and learning about turtles at Turtle Rescue of the Hamptons World Turtle Day, Jamesport
On Saturday, May 23, from 10 a.m. to 1 p.m, join us at World Turtle Day hosted by Turtle Rescue of the Hamptons. At this outdoor celebration dedicated to protecting New York’s native turtles, we’ll get to meet the sanctuary’s turtle ambassadors and learn about their rehabilitation work. Guided outdoor sanctuary tours will also be available, including a guided tour of the sanctuary, a behind-the-scenes look, and a chance to meet and learn about the resident turtles and their habitats. The celebration is free, but the guided tour costs $25/adult and is free for children under 12. Email turtlerescueofthehamptons.ny@gmail.com to reserve your tour spot.