Sign up for our Newsletter

Claudio’s reopens this month. (Credit: Madison Fender)

May begs us to get outside – dine al fresco, get in the garden, visit a farm, and more. Here are our top picks for things to do on the North Fork this May.

Make Main Street your canvas

Main Street in downtown Riverhead becomes a canvas for the community during this one-day event hosted by East End Arts as the street is turned into works of art in chalk. The Annual Mosaic Street Painting Festival will take place on Sunday, May 28, from noon until 5 p.m. This family-focused event, inspired by the street artists of Grazie di Curtatone, Italy, will include street painting for all, live music, interactive art, a kid’s zone, craft and artisan vendors, food trucks and local restaurants, and more. Visit their website for more details or to reserve an artist square. 

Get your garden going

The 27th Annual Garden Fest kicks off on Tuesday, May 9, and continues through Sunday, May 14, open daily from 9 a.m. to 6 p.m. This plant and shrub sale held at Tanger Outlets in Riverhead contains over 100,000 plants from the top 25 growers in the Northeast and benefits Peconic Bay Medical Center and Operation International. 

Celebrate Sundays at Bridge Lane 

Sunday, May 21, kicks off Bridge Lane Wine’s weekly event: Sunday Scaries with lounge vibes by DJ Henry Oh. Every Sunday during summer from 2 to 5 p.m. indulge in Bridge Lane Bubbles mimosas, North Fork Doughnut Co. doughnuts and live music. Check out the music lineup on their website and make a reservation while you’re at it. 

Play at the Farm 

Beginning on Wednesday, May 31, and running bi-weekly until Sept. 20, Browder’s Birds is launching Farm Tots. This program, for children between 18 months and 4 years old with a caregiver, includes exploring the farm, outdoor craft stations, free play and a snack. It runs from 9:30 to 11 a.m. and costs $35 per session. Sign up here.

Dog moms unite

Celebrate National Dog Mom’s Day at Corey Creek Saturday, May 13. Savor a “wags & wine” flight for $25, which includes four tastes for mom, a cup of Greenport Jerky Co. dog jerky and a Corey Creek dog bandana. Make sure your pooch is wearing their best and enter them into the doggy dress-up contest, which will occur later in the afternoon. All dogs must be present by 3 p.m. and judging will last until 3:30 p.m. This mommy-doggy day runs from noon through 4 p.m. and no tickets or pre-registration are required, but you can find more information here.  

Celebrate all things fleece and fiber

As one of Long Island’s largest celebrations of fleece and fiber arts, The Fleece & Fiber Festival is an immersive experience in the life cycle of fiber, from sheep to sweater. The event features dozens of fiber artisans showcasing their talents and selling their creations. This year will include a children’s activity area and a petting zoo. Watch a sheep shearing by Tabbethia Haubold-Magee of Long Island Yarn and Farm and spinners transforming raw fiber into yarn and weavers creating cloth. This festival will take place at Hallockville Museum Farm on Saturday, May 20 (with a rain date for Sunday, May 21) from 10 a.m. to 4 p.m. Admission is $10 per person. Tickets can be purchased in advance here or on the day of at the gate.

Dance the night away at Claudio’s

This Greenport tradition is back for the summer! Beginning Friday, May 19, head to Claudio’s Waterfront as the band Sahara kicks off the summer season. Listen and dance to music every Friday night from 10 p.m. to 1 a.m., Saturday from 1:30 p.m. to 5:30 p.m. and again at 10 p.m. to 1 a.m., and Sunday afternoons from 1:30 to 5:30 p.m. Check Claudio’s events page here for a full list of DJs and bands performing this summer.

Get Decked Out

Head to the George D. Costello Roller Skating Rink for its second Annual “Decked Out” Fundraiser on Saturday, May 20 from 1 to 4 p.m. Throughout the day, you can watch a runway fashion show and participate in a skate deck auction. This year, the event will integrate an athletic expo within the runway show, showcasing skateboarding, roller and inline skating, scooters and BMX. There will also be over 60 artists for the skate deck silent auction, doubling the number of artists since last year. ​All proceeds benefit the Greenport Skate Park Revitalization Project. Tickets are $10 per person and can be purchased through Greenport Skate Park’s website.

Oysters and wine, what more could you ask for?

Kick off the summer right with an afternoon full of oysters and wine at Suhru Wines Tasting Room in Cutchogue. Join Suhru along with Southold Bay Oysters Sunday, May 28 from 1 to 5 p.m. The complete Suhru menu will be available in addition to freshly shucked oysters. Parties are limited to six people. Make your reservation here

Spend your weekends walking in the garden

Opening for the season on Friday, May 5, take a walk among a picturesque landscape of lush gardens from around the world at Landcraft Garden Foundation. Beginning Friday, May 26, spend your afternoon on a guided tour of their four acres of magical gardens – where something is always in bloom. See their sculpture garden and even explore a subterranean “ruin” — topped by a green roof made of sedum. You’re invited to stroll down the mowed paths and learn about native plants and wildlife Fridays and Saturdays from 10 a.m. to 4 p.m. until October 28. Admission is $20 for adults, $17 for seniors and students, $5 for children under 12 and free children under 2 and all members.