21 Awesome Things to Do in the Hamptons This May

Like slipping into espadrilles and packing away the snow boots—or biting into chocolate soft serve—the Hamptons in May is a treat we eagerly wait for all year. The clam shacks are opening back up, the beaches are ready for lounging and the entire East End is throwing off its winter sleepiness. Hamptons season without the crowds is short and sweet. Get there now: The early bird gets dinner at their favorite restaurant without a reservation. Here’s the only to-do list you need this May.

7 Sandwiches Every Hamptonite Needs to Eat at Least Once

mantauk beach house pool
Courtesy of Montauk Beach House

1. Put on your best Derby attire, sip a mint julep and enjoy some Southern style food at the Montauk Beach House Derby Party, May 4.

2. Are there aliens among us?  Find out when Stony Brook University astrophysicist Phil Armitage talks interstellar visitors at Guild Hall on May 8.

3. See what the LongHouse Reserve is all about on May 17 when the 16-acre outdoor sculpture museum offers free tours for National Public Gardens Day.

4. Lace up your sneakers for a free Saturday morning dance party at the Southampton Arts Center on May 11.

5. You deserve a lobster roll. Get one at The Clam Bar at Napeague, now open for the season.

6. Laugh your butt off at Bay Street Theater’s All Star Comedy Show on May 11.

7. Pop into Sag Harbor’s LoveShackFancy and get your mom something luxurious for Mother’s Day. (The 1509 fragrance oils are a top pick.)

8. Sip a glass of rosé while keeping your toes firmly in the sand at Navy Beach. The popular seasonal spot’s wine list now includes 25 types of rosé from around the globe. 

9. Boogie down at the 10th annual Montauk Music Festival, May 16 to 19.

10. Take your favorite four-legged bestie for a hike at the third annual Paws in the Park at Hamptons Bay on May 18.

11. Meet your farmer with a tour of Sang Lee Farms on May 18.

12. Head to end for the annual Montauk Artists’ Association Juried Art Show, May 24 to 26.

hamptons surf club
Masahiro_Noguchi_NY/Getty Images

13. Surf’s up! But before you hit the waves, take part in the annual blessing of the boards, May 26 at St. Therese Lisieux Catholic Church.

14. Celebrate the unofficial start of summer while helping to raise money for the LGBT Network serving Long Island at the annual Hamptons Summer Kick-Off, May 25.

15. You know summer is just around the corner when Dan’s Rosé Soirée (May 26) descends on the East End with all the pink wine you could ask for.

terra glamping east hampton
Courtesy of Terra Glamping: East Hampton

16. Let the sound of the waves lull you to sleep when you stay at Terra Glamping, a full-service glamping company open in East Hampton’s Cedar Point County Park, May 24 through October. 

17. There’s never a bad time for a taco, especially at Amagansett’s newest restaurant, Coche Comedor—the latest project from the group behind Townline BBQ, Nick & Toni’s, Rowdy Hall and La Fondita.

18. You never know what you might find at Montauk’s Rummage Sale on May 25.

19. Box your way into summer with the Surf Lodge’s Memorial Day Weekend fitness program, which features classes from Gotham Gym, Bari Studio and Powerhouse Yoga.

20. You swooned over the nostalgic pop-up restaurant Jennie’s at Drossos in Greenport last summer; now check out the brother-and-sister team’s new brick-and-mortar spot, Ellen’s on Front.

21. Pick up a new beach tote or straw hat at Frances Valentine. The lifestyle brand started by Kate and Andy Spade and Elyce Arons opens a pop-up in Sag Harbor this month.

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Freelance PureWow Editor