Cozy Fall Harvest Escape Itinerary

2 Days / 1 Night

Theme: Autumn romance, farm-fresh flavors, and cozy coastal moments

There’s something special about the Hamptons in the fall. Crisp mornings, apple orchards, farm-fresh flavors, and quiet beaches set the scene for a getaway that’s equal parts cozy and refreshing. Whether you’re planning a romantic escape or a weekend with your closest friends, spend a couple of days savoring the season’s simple pleasures, from countryside strolls to sunset picnics and intimate dinners.


Day 1: Farm Fields, Apple Picking & Sunset Views

Morning | Breakfast at Amber Waves Farm

Begin your fall getaway at Amber Waves Farm. Enjoy a farm-fresh breakfast and explore the beautiful surroundings, where open fields and seasonal harvests offer a peaceful start to the day. Check for public access and seasonal café hours before visiting.

Afternoon | Apple Picking at The Milk Pail

Head to The Milk Pail U-Pick Farm for an afternoon in the orchard. Pick fresh apples, take in the autumn scenery, and embrace one of the East End’s most beloved fall traditions.

Late Afternoon | A Gourmet Picnic by the Beach

Stop by Cavaniola’s Gourmet to put together a picnic of artisan cheeses, charcuterie, and other gourmet favorites. Then make your way to East Hampton’s Main Beach, where the quieter shoreline creates a beautiful setting for a late-afternoon picnic and sunset stroll.

Evening | A Cozy Dinner in East Hampton

End your day with an intimate dinner at The Tavern at 1770 House, known for its historic charm and inviting atmosphere. For a more casual evening, try Lion’s Nook Bar & Grill for comforting fare in a cozy setting.

Day 2: Coffee, Village Strolls & a Little Culture

Morning | A Leisurely Start at Journey

Enjoy a slow morning at Journey before heading out for coffee and a stroll through East Hampton Village. Browse local boutiques, discover charming shops, and savor the unhurried pace of fall.

Afternoon | Catch a Film at Sag Harbor Cinema

Before heading home, make your way to Sag Harbor Cinema for a movie. This historic cinema is a fitting final stop for a cozy fall getaway, especially on a chilly or rainy afternoon.