Late Summer Events on the North Fork of Long Island: What Not to Miss

As summer is in full swing, the North Fork of Long Island comes alive with some of the season’s most unforgettable events. From vineyard concerts and wine tastings to farmers markets and food festivals, there’s no shortage of things to do on the North Fork in late summer. Whether you’re planning a weekend getaway or just looking for local fun in August, this guide will help you make the most of the final stretch of summer on Long Island’s beautiful East End.

Happy Hours at Little Creek Oysters in Greenport

Sip local wine, slurp fresh oysters, and soak up the harbor views during late summer happy hours at Little Creek Oysters in Greenport, a must-visit stop on the North Fork for seafood lovers. Wednesday Night Shucker’s Club is back and better than ever with oyster specials- raw, grilled and Shuck Your Self, plus drink specials and the killer $5 hot dog menu! Happy hour runs from doors open at 5pm and goes all night! 211 Carpenter Street Greenport, NY

Aldo’s Coffee shop X Disset Chocolate Paint Night in Greenport

Experience the ultimate creative evening in Greenport with a unique Paint Night collaboration between Aldo’s Coffee Company and Disset Chocolate—complete with rich espresso, artisan sweets, and hands-on fun. Join Disset at Aldo’s Coffee Company for a one-of-a-kind evening with chocolate painting, cocktails, and creativity in collaboration with Disset Chocolate. Paint with naturally colored cocoa butters on a canvas made entirely of chocolate. Sip on a tasting flight of espresso martinis. Indulge with our menu of craft cocktails, including two specials that are exclusive to this event! Space is limited – book now to reserve your canvas! 103-105 Front Street Greenport

Shakespeare’s Othello at Mitchell Park in Greenport

Catch a magical night of theater under the stars as Mitchell Park in Greenport hosts a live outdoor performance of Othello, bringing classic drama to Long Island’s scenic North Fork waterfront. Devised by The Company of Players using Shakespeare’s Original Practices. 7:00 PM FREE! Donations graciously accepted. Bring a chair or blanket! Don’t miss the loca theatre- its one of the best events of a North Fork Long Island Summer!

Alive on 25 Street Festival in Riverhead: July 18 and August 1

Alive on 25, Riverhead’s summer block party, is taking over Main Street and beyond with live music, craft beverages, local food, art, and family fun and a new downtown crawl to enjoy more beyond the street closure during the event and after hours! This walkable free event features over a dozen music spots, restaurant specials, artisan vendors, kids’ activities, car shows, Riverhead Race Cars, laser tag, local breweries and more! Additional live music and entertainment to be announced! Special fireworks display on the river behind the town square on July 18. Bring your lawn chairs to these events and enjoy live music everywhere. Schedules subject to change so check our social and website prior to the event. Theres nothing more quintessentially North Fork Long Island Summer than an Alive event!

For updates: aliveon25.org

Introduction to Herbalism class at Sang Lee Farms in Cutchogue

Learn the basics of plant medicine with a hands-on Introduction to Herbalism class at Sang Lee Farms in Cutchogue, blending education, wellness, and organic farming on the North Fork.  Join Kayla Barthelme in this foundational class, where we’ll explore the fundamentals of working with these incredible botanical wonders. You’ll learn the basics of using bioregional medicinal herbs to support your health and well-being. We’ll explore common herbal allies and their properties, along with the basics of creating safe and high-quality, albeit simple preparations like teas, tinctures, and salves. Sang Lee Farms 25180 County Rd 48. Tickets here.

Mattituck Park District Summer Concert Series

Enjoy free live music all season long at the Mattituck Park District Summer Concert Series, where local bands bring good vibes and great tunes to this laid-back North Fork community gathering. Join your friends and neighbors overlooking beautiful Peconic Bay for a  free concert staring The Eagle River Band. Bring your blankets and chairs. Food and beverages are available for purchase. Tickets here.

Riverhead Courtyard Concert Series: Mambo Loco

Get ready to dance in downtown Riverhead during the Courtyard Concert Series, featuring the energetic Latin beats of Mambo Loco—a perfect late summer night out on the North Fork. Mambo Loco is in the house! Concerts will begin at 5:30 p.m. and takes place in the library’s Front Entrance Courtyard. In case of bad weather, concerts are moved indoors. Attendees are encouraged to bring a lawn chair and enjoy the music. Riverhead Free Library 330 Court Street Riverhead Details Here

Tall Ship KALMAR NYCKEL Sails in Greenport

Step aboard history with a sail on the Kalmar Nyckel, a majestic tall ship docking in Greenport for public sails and dockside tours—an unforgettable maritime experience on Long Island’s North Fork. Adventure awaits when you take a 2.5-hour sail on Kalmar Nyckel, The Tall Ship of Delaware on July 22 to August 3 from the Village of Greenport. Haul lines, set sails, and hear tales from the crew, or simply relax and enjoy the ship. Discover the remarkable story behind Kalmar Nyckel, a full-scale replica of the 1638 Swedish merchant ship. Hands-on history and fun for all ages.

Tickets are available online (www.KalmarNyckel.org/explore) or by calling 302.429.7447 for $75 per adult and $40 per child 12 & younger. Advance reservations are highly recommended. Sails depart from the dock adjacent to the L.I.R.R. train station, 104 Fourth St., Greenport, NY 11944.