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  • Writer's pictureKaty Morris

The Off Season Guide to The Hamptons | Best Things To Do in The Fall, Winter and Spring

Updated: May 11, 2023

Pack your bags and head to The Hamptons during the off season. Vacationing in The Hamptons during the off season is a perfect time to explore the towns and villages without a crowd or needing endless reservations! The Hamptons has phenomenal restaurants, fun wineries, places to explore and walk, lots of history.

I highly recommend traveling to The Hamptons during the off season as it is peaceful, quiet and laid back. If you are looking to enjoy warmer weather, I suggest planning your trip during September (post Labor Day), October, April or the beginning of May (before the Memorial Day weekend crowds). Some restaurants have outdoor dining with heaters during the off season which allows for fun outside meals. Even during winter trips to The Hamptons, Mother Nature gives the occasional warm day to eat outside. If you travel to The Hamptons outside of the warmer off season months when it is snowing, the snows makes The Hamptons glisten in all its beauty!

The Hamptons have endless delicious restaurants that are open during the off season. Below are my favorite breakfast, lunch and dinner restaurants in The Hamptons during off season.

Baron's Cove - located in Sag Harbor, is a welcoming and cozy nautical themed restaurant that is open daily for breakfast and dinner. Baron's Cove has delicious food and drinks. After dinner, walk downstairs to the bar to enjoy live music and a drink by the fireplace.

Estia's Little Kitchen - is a fabulous breakfast restaurant with fresh and healthy meal options. I enjoy the vegan bowl that includes mixed vegetables, beans, sprouts, avocado and salsa. Estia's Little Kitchen is a popular location so expect a lively atmosphere!

Page at 63 Main - situated in the heart of Sag Harbor, is a fun dinner restaurant with outstanding food and cocktails. This is my staple restaurant in The Hamptons. I highly recommend the vegan grain bowl and the vegetable risotto paired with The Lawsuit cocktail.

Jean-Georges at Topping Rose House - in Bridgehampton, is an upbeat, elegant casual dining location with farm-to-table cuisine. The restaurant's colorful interior creates an inviting and bright atmosphere!

Tutto Il Giorno - is a chic Italian restaurant located in Sag Harbor. The first class service, beautiful interior and superb food makes Tutto Il Giorno a restaurant to dine at time and time again!

During the off season explore the wineries, lighthouse and beaches. Although it may be chilly, it is fun to take a walk on the beautiful beaches. Before going on your beach walk, pick up a warm beverage at Hampton Coffee Company. This will keep you warm for your stroll!

Duck Walk Vineyards - located in Water Mill, is a fun place to try great wines! I thoroughly enjoy the wine tasting and always buy plenty of the excellent wine to take home. When you sample the blueberry wine, ask for a piece of chocolate - eat the chocolate first then sample the wine - this makes for the perfect pairing. I especially recommend the Vidal Blanc Ice Wine, Gatsby Red and Aphrodite.

Wolffer Estate Vineyards - is an upscale wine tasting experience with an elegant interior. I enjoy ordering a wine flight with a hummus platter. They have numerous wine flight options as well as a variety of small bites. The rich and luxurious environment, delicious wines, good food and pretty vineyard views make it a memorable stop on your trip!

Hank's Pumpkintown - situated across the street from Duck Walk Vineyards is an outdoor fun zone filled with pumpkin and apple picking, a corn maze, interactive games and activities as well as freshly baked sweet treats. It is a definite must fall activity, however, unfortunately it is closed during the winter months.

Montauk Lighthouse - is an historic and scenic place to visit. In addition to the incredible views where you can see Rhode Island, Connecticut and Block Island, there is plenty to learn. Bring lots of questions as the Montauk Lighthouse staff is incredible knowledgeable. Before or after touring the lighthouse and walking the grounds, explore Camp Hero located next to the Lighthouse.

Happy Traveling!



Katy Covey Morris The Collection By KCM


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