48 Hours in the Hamptons: Memorial Day Weekend Itinerary to Start the Season
Memorial Day weekend marks the official start of the Hamptons summer season. It’s one of the most visited weekends of the year, when travelers from New York City and beyond arrive on the East End to celebrate the beginning of warm weather, beach days, and outdoor dining.
If you’re planning a quick getaway, this 48-hour itinerary will help you experience some of the best things the Hamptons have to offer.
Day 1: Explore the Hamptons Towns
Start your Memorial Day weekend exploring one of the East End’s iconic towns.
Popular places to visit include:
• Southampton Village — historic streets, boutiques, and restaurants
• Sag Harbor — waterfront charm and art galleries
• East Hampton — classic Hamptons scenery and beaches
https://easthamptonvillage.gov/beach-rules/
Take time to stroll through Main Streets, enjoy local shops, and discover the unique personality of each town.
Coffee lovers can begin the day with one of the local cafés featured in our guide:
Best Coffee Shops in the Hamptons
Afternoon: Head to the Beach
No Memorial Day weekend in the Hamptons is complete without time by the ocean.
Some of the most popular beaches include:
• Cooper’s Beach – Southampton
• Sagg Main Beach – Sagaponack
• Atlantic Avenue Beach – Amagansett
These beaches offer wide sandy shorelines and scenic Atlantic views that make the Hamptons famous.
Before heading out, check local regulations and permits:
Hamptons Beach Permits & Rules
Official beach information
Evening: Dinner on the East End
After a day exploring the coast, enjoy dinner at one of the many restaurants across the Hamptons.
Local seafood and outdoor dining are especially popular during Memorial Day weekend.
For recommendations, explore:
Hamptons Dining & Activities Guide
Or try a classic East End favorite:
Day 2: Vineyards, Farms & Scenic Drives
Spend your second day discovering some of the East End’s scenic countryside.
Visitors often enjoy:
• Wine tastings
• Farm stands and markets
• Scenic drives along the coast
One of the most well-known vineyards in the Hamptons is:
It’s a beautiful spot to relax with a glass of rosé and take in the surrounding vineyard views.
Stay Tuned for Our 2026 Opening Season
Hamptons Vacation Inn reopens May 22, 2026, just in time for Memorial Day weekend and the start of the Hamptons summer season.
Located in Hampton Bays, the property provides convenient access to beaches, restaurants, and many of the East End’s most popular towns.
📞 (631) 728-1158
📲 Follow @hamptonvacation on Instagram for weekly event guides, travel tips, and local recommendations throughout the season.