East End Summer 2023 Calendar: Can't Miss Events in the Hamptons & North Fork

Plan your summer 2023 on the East End with the most important can’t-miss events and activities in the Hamptons and North Fork from May–September.

East End Summer 2023 Calendar Highlights

May

Memorial Day Weekend at the Southampton Social Club
Friday-Sunday, May 26–28

Don’t miss a kickin’ weekend and a sparkling way to start the summer at the Southampton Social Club, where DJ Lomo, DJ Joey Sik and Jes Button will keep you rockin’. Reserve your spot ahead of time for dinner and bottle service
256 Elm Street, Southampton. 631-287-1400, southamptonsocialclub.com

Memorial Day Weekend at Gurney’s
Friday-Sunday, May 26–28

Enjoy the holiday in style at Gurney’s resort, where the weekend-long celebration includes live music, wine tastings, a beach bonfire and a brunch buffet. Take advantage of beach chairs and umbrellas at the Beach Club while you’re there.
290 Old Montauk Highway, Montauk. 631-668-2345, gurneysresorts.com

Yoga in the Vines
Saturdays and Sundays, 9–10 a.m.

Don’t miss the 10th season of Yoga in the Vines in the bucolic fields of Wölffer Estate, beginning on May 27. Outdoor classes are available Saturdays and Sundays from 9–10 a.m. and 10:15–11:15 a.m. There is a drop-in fee of $38 or you can purchase class packs.
139 Saag Road, Sagaponack. 631-537-5106, wolffer.com

Beginner Country Line Dancing at the Barn
Mondays in May

If you like to do-si-do, you can do-si-do it in style at Spirit’s Promise Rescue on Monday nights throughout the summer. All proceeds will go to benefit the horses and rescue programs. An improver-level class will also be offered.
2746 Sound Avenue, Riverhead.631-875-0433, spiritspromise.com

Planting Day
Friday, May 26, 4–5:30 p.m.

Head to Amber Waves Farm to celebrate the beginning of summer by planting your own lettuce box and learning how to care for teenaged plants at home. Tickets are $60.
367 Main Street, Amagansett. 631-267-5664, amberwavesfarm.org

Mighty North Fork Triathlon
Sunday, May 28

You’ll be flipping your fins for this popular triathlon appropriate even for beginners, with a calm Peconic Bay swim, mostly flat 7-mile bike ride and scenic 3.5-mile run. Register ahead of time and meet at Cedar Beach in Southold.
3690 Cedar Beach Road, Southold. trisignup.com/Race/NY/Southold/MightyNorthFork

Run the Vineyards 5K at Pindar Vineyards
Sunday, May 28, 9 a.m.

Experience wine country in athletic style with a flat 5K through Pindar Vineyards. You’ll also take in live music by Paris Ray, a food truck, a complimentary glass of Pindar wine and a full wine and tasting menu.
37645 Main Road, Peconic. 631-734-6200, pindar.net

Mosaic Street Painting Festival
Sunday, May 28, noon–5 p.m.

Welcome summer in lots of colors in Downtown Riverhead, where you’ll enjoy sidewalks converted into works of art. There’s also live music, street vendors, a Kidz Zone, food trucks, a drum circle and performances.
Downtown Riverhead. eastendarts.org

Dan’s Rosé Soirée
Sunday, May 28, 7 p.m.

Enjoy music, food and beverages from many local restaurants and wineries at the Southampton Arts Center. You can also purchase VIP access and party packages.
25 Jobs Lane, Southampton. danstaste.com/events/rose-soiree

June

Pechakucha Night Hamptons
Friday, June 2, 6 p.m.

Don’t miss your chance to meet many wonderful creatives who call the East End home. Artists, musicians, gardeners, farmers and designers will join the Parrish Art Museum for Pechakucha, a great opportunity for networking and information.
279 Montauk Highway, Water Mill. 631-283-2118, parrishart.org

All Against Abuse Benefit
Saturday, June 3, 6 p.m.

Attend a wonderful benefit and support violence prevention and counseling for those who have been abused. The event will take place at The Church in Sag Harbor, but there will also be an online auction.
48 Main Street, Sag Harbor. 631-329-4398, allagainstabuse.org

Full Moon Paddles in the Hamptons
June 3, July 3, August 1, August 30, 6–9 p.m.

Join JB Yoga as you enjoy that magical time when the sun sets and the moon rises in the lovely summer sky. You’ll launch from the beach and spend about 30-40 minutes stand-up paddling before the sun sets. A quick lesson will be available for newbies. Afterward, bask in the glow of a bonfire with organic snacks.
Hamptons. jbyoga.com

Comedy Night at CAST
Saturday, June 3, 7–10 p.m.

Don’t miss this exciting night featuring the best comedians on Long Island. Your ticket purchase will benefit CAST, which helps families in need throughout the East End.
53930 Main Road, Southold. 631-477-1717, castnorthfork.org

Candlelight Hamptons: a Tribute to Taylor Swift
Tuesday, June 6, 6:30 and 9 p.m.

Don’t miss this live, multi-sensory experience honoring the music of Taylor Swift at the Clubhouse. Selections will be performed by DIVISI’s Amp’d String Quartet.
174 Daniels Hole Road, East Hampton. feverup.com/m/126789

Dr. Stanley Epstein Memorial Golf and Tennis Outing
Wednesday, June 7, 9 a.m.

Enjoy a full breakfast at the elegant Westhampton Country Club to tee off this exciting day and raise money for the Westhampton Beach Performing Arts Center. Round off the outing with lunch and a cocktail party.
35 Potunk Lane, Westhampton Beach. whbpac.org

Taste the East End
Saturday, June 10, 7–10:30 p.m.

Swim on over to the Long Island Aquarium to enjoy food, craft beer, wine and live music. Tickets are $85 and reservations are required.
431 East Main Street, Riverhead. 631-208-9200, longislandaquarium.com

Montauk Blessing of the Fleet
Sunday, June 11, 5–7 p.m.

Don’t miss the annual Blessing of the Fleet, when boats will be decorated with colorful flags and line up in the harbor for the clergy to bless. Commercial boats, sailboats, private yachts and Boston Whalers will all participate.
Montauk Harbor, Montauk. montaukchamber.com/event/blessing-of-the-fleet

Mattituck Lions Strawberry Festival
Wednesday–Sunday, June 14–18

You won’t want to miss this annual East End event that’s bursting with flavor. You’ll enjoy live music, craft vendors, rides, a talent show and strawberries prepared in every way imaginable.
1175 Route 48, Mattituck. mattituckstrawberryfestival.org

Sunset Cruise Fundraiser
Tuesday, June 20, 6:30 p.m.

Enjoy an evening of life music, drinks and dancing benefiting the Montauk Chamber of Commerce, setting sail from the Montauk Yacht Club.
32 Star Island Road, Montauk. 631-668-2428, eventbrite.com/e/sunset-cruise-fundraiser-tickets-577740105207?aff=ebdsoporgprofile

Dan’s Chefs of the Hamptons
Thursday, June 22, 7 p.m.

Enjoy delectable bites paired with over a dozen local wines while overlooking the bay at the exclusive EHP Resort & Marina. Oysters, Champagne and caviar are all part of the fun.
295 Three Mile Harbor Hog Creek Road, East Hampton, danstaste.com/events/chefs-of-the-hamptons

Heart of the Hamptons Summer Celebration
Thursday, June 22, 6–9 p.m.

Don’t miss premier food and beverages, a silent auction, lawn games and live music at the Wine Stand at Wölffer Estate. Proceeds will benefit the American Heart Association.
Sagaponack. 516-962-0792, ahalongisland.ejoinme.org/MyEvents/20222023HamptonsHeartBall/tabid/1339648/Default.aspx

Garden as Art 2023
Saturday, June 24

Don’t miss this event featuring a morning talk and self-guided tour of four private East Hampton Village gardens to benefit Guild Hall. If you purchase a Patron Ticket, you’ll also enjoy a cocktail prolongé hosted by Cornelia and Ralph Heins.
East Hampton. 631-324-0608, guildhall.org

Get Wild! Benefit
Saturday, June 24, 4–7 p.m.

Enjoy live music, drinks and appetizers in the Sagaponack Sculpture Field. All proceeds will go to benefit the native wildlife treated at the Evelyn Alexander Wildlife Rescue Center.
Wilkes Lane, Sagaponack. eventbrite.com/e/15th-annual-get-wild-benefit-tickets-595769601917

Cutchogue Lions Club Fundraiser
Sunday, June 25, 9 a.m.–4 p.m.

Don’t miss this exciting fundraiser at Pindar Vineyards featuring food trucks, beer, wine and a “People’s Choice” contest judging cars, bikes and military vehicles. Tickets are $5 for adults and free for children.
37645 Main Road, Peconic. cutchoguelions@gmail.com, cutchoguelionsclub.com

An American Picnic with Fireworks by Grucci
Friday, June 30, 7–10 p.m.

Enjoy this annual East End sparkling party featuring a carnival with games, stilt walkers and magicians, as well as a delicious American picnic, music and dancing. And of course, you’ll want to stick around for magical fireworks displayed over Shinnecock Bay!
Meadow Lane, Southampton.631-283-5847, sfah.org/americanpicnic

July

John A. Ward Independence Day Fireworks
Saturday, July 1, 9:30 p.m.

Get in the summer spirit at the Sag Harbor Yacht Club, with fireworks in honor of the Fourth of July. This is a popular tradition among the Sag Harbor community.
27 Bay Street, Sag Harbor. 631-725-0567, sagharboryc.com

Fourth of July Weekend Celebration at Harbes Farm
Sunday–Tuesday, July 2–4

Have some crackling fun at Harbes Farm, where you’ll enjoy live music, a barnyard adventure, wine tastings and a concession stand. Your kiddos can also enjoy bounce pillows, an obstacle course, pig races and even an animatronic chicken show.
715 Sound Avenue, Mattituck. 631-482-7614, harbesfamilyfarm.com

Fireworks at Umbrella Beach
Tuesday, July 4, 9–10 p.m.

Bring out your beach chairs and enjoy this sparkling event sponsored by the Montauk Chamber of Commerce. A Fireworks Cruise will begin at 6 p.m.
Umbrella Beach, Montauk. montaukchamber.com/event/fireworks-cruise

2023 Bay Street Gala
Saturday, July 8, 6:30 p.m.

Line up for dinner, dancing and a live auction at Sag Harbor’s own Bay Street Theater. This year’s honorees include Sara Jessica Parker, Matthew Broderick and Julie Andrews. Funds raised will go to support the work of the Bay Street Theater.
1 Bay Street, Sag Harbor. 631-725-0818, baystreet.org

Dan’s Papers — Gurney’s Clambake
Thursday, July 13

Don’t miss appetizers, seafood, wine and cocktails with oceanfront views at Gurney’s. Purchase a platinum ticket and you’ll also enjoy a bonfire afterparty with cocktails and desserts.
290 Old Montauk Highway, Montauk. danstaste.com/events/clambake

Art in the Park
Saturday and Sunday, July 15–16, 10 a.m.–6 p.m.

Enjoy over 45 exhibitors selling their paintings, sculpture and mixed media.
51 Pond Lane, Southampton. festivalnet.com/81945/Southampton-New-York/Art-Shows/Art-in-the-Park

Hamptons Fine Art Fair
Thursday–Sunday, July 13–16

Take part in this boutique, curated fine art fair especially designed for avid collectors and investors. Enjoy an intimate, casual setting and lots of upscale art.
605 County Road 39, Southampton. hamptonsfineartfair.com

The Clamshell Foundation Fireworks Show
Saturday, July 15

View the Fireworks over Three Mile Harbor while listening to music simulcast on WLIW-FM with host Brian Cosgrove. The rain date is Sunday, July 16.
Three Mile Harbor, East Hampton. clamshellfoundation.org/fireworks

Montauk Lighthouse Triathlon
Sunday, July 16, 6:30 a.m.

Don’t miss your chance to enjoy one of the best finish lines around! You’ll swim a half-mile starting at Gin Beach, bike 14 miles through Montauk and around Gosman’s Dock and finish at the lighthouse, where you’ll run a 5K through spacious paved roads.

2000 Montauk Highway, Montauk. trisignup.com/Race/NY/Montauk/LighthouseTriathlon

The Lords of Menantic Musical
Thursday–Sunday, July 20–23, 6 p.m.

Don’t miss this musical written and directed by Lisa Shaw and presented at the Shelter Island Historical Society. It’s the story of three sea captains and two maiden sisters who owned a beautiful estate on the Menantic peninsula in 1804.
16 South Ferry Road, Shelter Island. 631-749-0025, shelterislandhistorical.org

Summer Soiree
Friday, July 21, 6 pm.

Enjoy this tented event benefiting East End Arts overlooking the Peconic River. You’ll take in wine, beer and delicious cocktails from local favorites. There’s also live entertainment and a live auction.
Riverhead. eastendarts.org/featured-events/summer-soiree

Polo in the Hamptons
Saturdays, July 22 and 29, 4–7 p.m.

Enjoy a polo match along with an open bar, appetizers and preferred seating. Tickets are limited and the event will take place rain or shine.
900 Lumber Lane, Bridgehampton. admin@polohamptons.com, polohamptons.com

Midsummer Dream
Saturday, July 22, 6 p.m.

Don’t miss your chance to support Longhouse Reserve and view its iconic gardens, sculptures and plants. Music, cocktails and food will all help to make it an evening you won’t forget. Purchase tickets for singles, couples or tables.
133 Hands Creek Road, East Hampton. 631-329-3568, longhouse.org

Paddle Battle 2023
Saturday, July 29

Enjoy this exciting race for paddlers at all levels to help raise money for the not-for-profit NY Foundation to save the turtles.
Riverhead Waterfront, paddlebattleli.com

The Body: The Watermill Center’s Annual Summer Benefit
Saturday, July 29, 6–9 p.m.

Enjoy this dynamic event featuring works by a variety of groundbreaking international artists. Performances and installations will take place throughout the property. Proceeds will go to benefit the Watermill Center, a home-away-from-home for artists from all over the globe.
39 Water Mill Towd Road, Water Mill 631-726-4628, watermillcenter.org

34th Annual Summer Gala
Saturday, July 29, 6–10 p.m.

Join the South Fork Natural History Museum for their annual Summer Gala featuring guest hosts like Yvon Chouinard, the founder of Patagonia and Dan Emmett, founder of UCLA’s Emmet Institute. You’ll enjoy a VIP cocktail reception and a tasting menu served up by favorite local eateries, as well as dinner and dancing.
377 Bridgehampton-Sag Harbor Turnpike, Bridgehampton. 631-903-7217, sofo.org

Hallockville Barn Dance Fundraiser
Saturday, July 29, 6–9:30 p.m.

Don’t miss this family-friendly event with Chart Gutherie, who has been calling dances since he was in fifth grade and always works with live music. Children are welcome.
6038 Sound Avenue, Northville 631-298-5292, hallockville.org/barn-dance

August

Cardboard Boat Race
Saturday, August 5, 9 a.m.

Create your own vessel using cardboard and duct tape and watch it set sail on the Peconic River! A Youth Regatta, Grand National Regatta, games, activities and an awards show will all be part of the fun.
Downtown Riverhead. 631-440-1350, downtownriverhead.org

Dan’s Grillhampton
Saturday, August 5, 7 p.m.

Don’t miss this delicious competition pitting six East End chefs against six Manhattan chefs at The Clubhouse Hamptons. You’ll enjoy tasty bites, cocktails and live music.
174 Daniels Hole Road, East Hampton.danstaste.com/events/grill-hampton

17th Annual Lecture Luncheon Benefiting the East Hampton Historical Society
Thursday, August 10, 11 a.m.

Join acclaimed author Stephen Sills as he discusses his third book, A Vision For Design, at the Maidstone Club. He will talk about his current projects at some of the most luxurious homes in the country, including several on the East End.
50 Old Beach Lane, East Hampton. 631-324-6850, flipcause.com/secure/cause_pdetails/MTc4OTk3

Dan’s Taste X Gurney’s
Thursday, August 17

This fine dining event unites the talents of renowned chefs who lead top resorts for a one-of-a-kind event. VIP tickets include a Champagne toaste with the chefs and a beach bonfire.
290 Old Montauk Road, Montauk. danstaste.com/events/taste-of-montauk

Art Show on the Green
Friday–Sunday, August 18–20

Enjoy a juried art show featuring the works of local painters, sculptors and ceramicists. Apply early to be an exhibitor.
Montauk. montaukartistsassociation.org

75th Annual East Hampton Artists & Writers Charity Softball Games
Saturday, August 19, 2 p.m.

Enjoy hot dogs, hamburgers and ice cream while playing ball and raising money for those in need on the East End. The suggested donation is $10 per person.
67 Newton Lane, East Hampton. awgame.org

Bow Wow Meow Ball
Saturday, August 19

Enjoy an evening of dinner and dancing at The Clubhouse while you celebrate the Animal Rescue Fund of the Hamptons’ Home Project Team. You’ll also view a parade of animals, which you’ll be helping to support with your ticket.
124 Daniels Hole Road, East Hampton. give.arfhamptons.org

Ellen Hermanson Foundation Summer Gala
Saturday, August 26, 6:30 p.m.

Enjoy a night under the stars with dinner and music at the Bridgehampton Tennis and Surf Club. The Ellen Hermanson Foundation supports patient-centered care for those diagnosed with breast cancer.
231 Midocenan Drive, Bridgehampton. ellenhermanson.org

Box Art Auction
Saturday, August 26, 4–8 p.m.

Don’t miss this time-honored tradition benefiting East End Hospice. You’ll bid on boxes created by local artists featuring everything from landscapes to abstract art. Boxes can be previewed on August 23 and 24.
18 James Lane, East Hampton. eeh.org

Hampton Classic
Sunday–Sunday, August 27–September 3

Round off the summer in style at the Hampton Classic, one of the largest horse shows in the country, featuring the finest riders from around the world competing for over $800,000 in prize money. While you’re there, enjoy 80 on-site shops, lots of international food options and daily activities in the kids’ area.
240 Snake Hollow Road, Bridgehampton. 631-537-3177, hamptonclassic.com

September

Shinnecock Powwow
Friday–Monday, September 1–4

Celebrate one of the largest Native American gatherings on the East Coast in the Hamptons. Enjoy drum and dance contests, food, crafts and three sunset fire lightings. Tickets are $20 for adults and $10 for children, seniors and military members.
Southampton. 631-283-6143, shinnecock-nsn.gov/annual-powwow

Westhampton Beach Festival of the Arts
Saturday and Sunday, September 2 and 3

Get out and about on Labor Day weekend to enjoy wonderful art on the Great Lawn across from St. Mark’s Episcopal Church in Westhampton Beach. Admission is free.
Great Lawn, Westhampton Beach. festivalnet.com/43051/Westhampton-Beach-New-York/Art-Shows/Westhampton-Beach-Festival-of-the-Arts