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22 Things to Eat, See and Do in the Hamptons This May

Dear weather gods: We’ve had enough. One minute we’re outside strolling through the park, the next we’re back to hibernating indoors while a frigid rain pours down. We’re ready for alfresco brunches, followed by afternoons of rosé tastings and nights listening to live music. Here’s everything to put on your Hamptons agenda this month (fingers crossed the forecast cooperates).

The Best Dog-Friendly Spots in the Hamptons


1. Make your reservations now. EMP Summer House reopens on May 25.

2. Have your first beach outing of the season. The water's not quite warm enough for a swim, but it’s a lovely time to stroll along Coopers Beach and gawk at all the fancy beach cottages.

3. Don your fanciest hat for the Lyzon Hat Museum’s Kentucky Derby party.

4. Use Cinco de Mayo as your excuse to eat too many tacos at Amagansett’s La Fondita.

5. While away a Saturday afternoon listening to music and sipping rosé during Bridge Lane Wine’s live music sessions.

6. Head to LT Burger on the first hot day and indulge in the most decadent-looking milkshake on their menu. You deserve it after the winter and early spring we had.

7. Get up close and personal with the horses at Amaryllis Farm Equine Rescue during Mommy and Me every Saturday.

8. Feel the burn while getting into a summer fitness routine with a class at East End Row.

9. It’s finally outdoor-dining season. Dine alfresco at all of your favorite restaurants, like Calissa, Navy Beach and Rumba

10. Take a walk through the stunning gardens at LongHouse Reserve.

hamptons festival crowd stage
Montauk Music Festival/Facebook

11. Check out the 9th Annual Montauk Annual Music Festival from May 17 to 20. More than 75 bands and singer-songwriters will descend on The End to play at more than 30 different venues.

12. Marvel at the incredible work of more than 300 local artists during the 80th Annual Guild Hall Artist Members Exhibition through May 19.

13. Have your first spring picnic at Good Ground Park in Hampton Bay during Concert in the Park on May 20.

14. Treat your mom on Mother’s Day brunch at one of your favorite spots, like Claude's Restaurant or Tillie’s at Gurney’s Montauk Resort.

15. Sip Long Island vino while strolling through the vineyards and learning about the wine-making process from Sannino Vineyard owner and winemaker Anthony Sannino during a Vine to Wine Tour.

16. You never know what you might find at Montauk Community Church’s Rummage Sale on May 26.

17. Browse through vintage furniture, jewelry, artwork and more at Southampton Treasures and Collectables Fair on May 26.

18. Kick off the unofficial start of summer with a cocktail reception for a good cause. The LGBT Network will celebrate summer 2018 at the Bridgehampton Tennis and Surf Club on May 26.

19. Nab some of the East End’s bounty when the Southampton Farmers Market reopens for the season on May 27.

20. Sip and savor the finest rosés from the Hamptons, the North Fork and beyond on May 27 at Dan’s Rosé Soirée.

21. Surf lovers, make sure you head to the 8th Annual Blessing of the Boards on May 27 before hitting the waves.

22. Explore charming Sag Harbor at the Sag Harbor Memorial Day Parade on May 28 while honoring service members who made the ultimate sacrifice. 



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Freelance PureWow Editor