Enjoy the East End Al Fresco. 
From Riverhead to Orient to Montauk

The Eastern End of Long Island, New York City’s backyard beach getaway, offers a variety of fun activities for all ages and interests. From Riverhead to Greenport to Montauk, there are the Hamptons, North Fork farms and vineyards, breweries, scenic beaches, and stunning views. From tall ship festivals to music festivals to drag racing events, to the Long Island Aquarium, Splish Splash, and the Parrish Art Museum, there’s something for everyone.

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Highlighting the best of the Hamptons and North Fork summer season encompasses dozens of  festivals, outdoor recreational activities, live music and more for couples and families of all ages. The majority of these events take place during the day or on the weekends, with several that span the course of a half or full week.

Below are a few summer events on the East End to help make the most of your getaway.


Reflextions Riverhead

Grangebel Park (Milton L. Burns Park), Riverhead

June 29th  |  August 3rd  |  September 7th  |  7p – 10p

Reflextions is a free, interactive, walkable public art space that takes place in the summer, June – September with an OKTOBERFEST event October 5th. The events feature assorted elements of light based on artist interpretations and designs including LED, fire, Dayglow, and photoluminescent displays. Each illumination event will feature Live Music. 

Rites of Spring

The Rites of Spring Music Festival is an annual event that takes place across the North Fork and the East End of Long Island on various dates throughout the summer. The music festival has quickly become the premier classical and contemporary music festival on the North Fork. In addition to great music, locals and visitors can enjoy a great local food and wine paired with an historic setting and inspiring artist talks. 

2024 Summer Calendar:

Wednesday June 26th,  6p

Music from around the World 

Gil Goldstein, accordion Laura Metcalf, cello Rupert Boyd, guitar

Poquatuck Hall in Orient

Thursday July 4th, 7p- 8:30p

Americana at the Village Green 

MudFlats String Ensemble

American traditional music

Village Green in Cutchogue in Cutchogue

Saturday July 13th, 5p

Le Remede de Fortune 

Medieval Songs of Fate, Fortune & Fin’ amor

Concordian Dawn Music Ensemble

Landcraft Garden Foundation in Mattituck 

Saturday, July 27th, 7p

Spirit in The Machine 

Sinta Saxophone Quartet

Custer Astronomical Observatory in Southold


Sunday August 25th, 6p

Rustic Mid-Summer Concert

Sami Merdinian, violin, Yezu Elizabeth Woo, violin, Hector Del Curto, Bandoneon

McCall Vineyard in Cutchogue

Sunday September 8th, 1p- 3p

Brunch & Vocal Concert at Borghese Vineyard

Susanna Phillips, soprano, Tom Manuel, trumpet, Steve Salerno, guitar

Castello di Borghese Vineyard

Alive on 25

Main Street, Riverhead

July 5th  & August 9th  |  (rain dates) July 19th & August 23rd  

5p – 9:30p

Alive on 25 is a popular, free annual event in downtown Riverhead taking place on two very special Fridays in July and August. The event offers local craft beverages and wine, live music on multiple stages, a car show, artists, street vendors, and activities the whole family can enjoy. The walkable, pop-up festival on main street also features restaurant offerings and specials, artist exhibitions, and much more. There will also be a firework display on July 5th and a laser light show on August 9th at 9 pm.

Jamesport Firemen’s Association Annual Bazaar and Parade

George Young Community Center, Main Road, Jamesport

2024 Schedule: Tuesday- Saturday TBD

A summertime favorite on the North Fork, the Jamesport Firemen’s Association hosts their annual carnival full of exhilarating rides, captivating games and mouth watering bites to eat.  On Wednesday night, the community gathers to pay tribute to local heroes in the Jamesport Parade, and the spectacular fireworks show by the Jamesport Fire Department ends the week’s festivities on Saturday night!

Long Island Farm Experience

Waterdrinker Family Farm & Garden, Riverhead

Saturday, July 20th – Friday, August 2nd  |   10a – 6p

The Long Island Farm Experience aka LIFE is having its grand opening ceremony at the Waterdrinker Family Farm & Garden on July 20th. LIFE is a celebration of one-hundred years of rich, natural history right in our own backyard! Long Island is home to hundreds of farms and Waterdrinker invites us all to learn a little bit more about the importance of farming while having loads of fun! The event hosts a variety of activities including Walter Drinker’s Waterdrinker Express, the Fun Farm Facts Game Show, LIFB Beer Garden and a planting workshop. On Wednesdays through Sundays there’s even more fun to be had with barnyard animals, a farming museum, miniature golf, jumbo jump pads, adventure avenue, sand castle slide, pedal car raceway, basketball hoops, wooden play area, vintage tractors, & tons of photo opps!

a both days, as well as a corn eating contest, plus the opportunity to explore Harbes Barnyard Adventure that offers plenty of fun for the whole family. Admission includes a Musical Hayride tour of their 100-acre farm, famous Pig Races, adorable farm animals, and much more.

Paddle Battle

Peconic Riverfront, Riverhead

Saturday, July 27th

Paddle Battle is an annual event that benefits the NY Marine Rescue Center is a rescue and rehabilitation organization that promotes marine conservation. There are two separate races. One is a 2 1/2 mile recreational race, the second is a competitive 5 mile race. There are different categories per race. For instance, categories include recreational kayak, stand up paddle boards and more, depending upon the race. Estimated race start times will be given at check-in. CLICK HERE for more Individual race details and to register and CLICK HERE for Team Challenge.

Cardboard Boat Races

Peconic Riverfront, Riverhead

Saturday, August 3rd   |  9a Registration  &  11a Races

Grab your cardboard and duct tape and get crafty! One of Riverhead‘s most exciting summer events is The Annual Cardboard Boat Races. Participants have the opportunity to race in various categories including the Youth Regatta, Grand National Regatta and more. Prizes are given out for the best spirit, best captain, best constructed, most creative, and more. Online pre-registration is required.

The Hampton Classic

Snake Hollow Road, Bridgehampton

August 25th – Sept 1st

The Hampton Classic Horse Show is a longtime annual Hamptons event that traditionally takes place over the last week of August until right before Labor Day. Well into its fourth decade, it is one of the largest outdoor horse shows in the United States and is widely popular for everyone of all ages. At this week-long show, top equestrians from around the world compete for more than $800,000 in prize money. National champion hunter competitors, Olympic medalists, and scores of children and adult amateurs make up the field throughout the event.


In addition to watching world class equestrian sport, event goers enjoy onsite boutique shops, International food stations and food trucks, daily activities in the kids’ play area and more. 

Day and weekly passes are available for purchase as are individual and carload tickets.

Garlic Festival

Waterdrinker Family Farm & Garden, Riverhead

Saturday, September 14th & Sunday, September 15th  |   9a – 6p

The 22nd Annual Garlic Festival will be back in Riverhead this season at the Waterdrinker Family Farm & Garden! This festival is all about celebrating the harvest season with live music, the local garlic vendor market, food trucks and family fun! This event is jam-packed with fun adventures! Take a stroll through the sunflower fields, grab a few pumpkins in the picking field, get lost in the Corn Maze, explore Waterdrinker’s Adventure Avenue, go on a Garlic Scavenger Hunt, or learn all about Garlic on the Musical HayRide. You won’t want to miss this!

Annual Maritime Festival – Greenport Village

Saturday, September 21st  &  Sunday, September 22nd   |   10a – 5p

Hosted by the East End Seaport Museum, the Annual Maritime Festival celebrates all things nautical and marks the end of the summer season on the East End. With over 100 artisan craft and food vendors to explore, weekend highlights include the Merfolk Parade (Sat. 11a), kayak and cardboard regatta races, sea shanty performances, live music, children’s activities and Mermaids!