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Hamptons.com
September 27, 2022

10 Reasons Why the Hamptons is Awesome in the Fall

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Veronica Chumbiby Veronica Chumbi
in Community, Trending
Home Community

I get it. Summer is over and we are all a little sad about it. But now it’s fall in the Hamptons and this is arguably just as good. Aside from the wonderful weather and fewer crowds, Fall in the Hamptons is very special. Here are the top ten reasons why it’s awesome. 

 

Pumpkin picking – That’s right, I said it. Pumpkin picking. It’s such a fun thing to do with your kids or even your friends if you’re looking for a laugh. Nothing beats Hank’s Pumpkin Town with your family, it’s ear to ear smiles all day. 

 

Fall Restaurant Specials – Because it’s fall, restaurants in the Hamptons no longer tell you that they don’t have a table available and brush you away. The exact opposite happens and restaurants are always coming up with creative ways to keep the locals coming in. Most of the top restaurants out here offer great Fall Prixe Fixes for less than $30. This is a great opportunity to hit up those places that you missed this summer. 

 

Jazz At Wolffer Vineyards – Nothing beats it and it goes on into the winter. Live music, Wolffer wine, lights on the vines as you get deeper into the season, it’s just the best. 

 

Outdoor Firepits – Suddenly, that outdoor firepit that you have in your backyard that you never used during the summer makes a lot of sense. The cool air makes an outdoor firepit feel like a campfire, and with night coming earlier, a nice evening can end by 9pm as you cozy up with your friends by the fire and share stories. 

 

Corn Mazes – My favorite one is located at Mecox on Fairview farm. Not only is the corn maze a blast but they have incredible snacks to enjoy like their homemade French fries with home grown potatoes. 

 

The Montauk Farmers Market in October- This farmers market is just the best and it is a great way to spend part of your day in Montauk during the off season. Speaking of good places in Montauk… 

 

The Montauk Brewing Company – Fall at Montauk Brewing Company is like a celebration of life. The entire brewery forms in a crowd outside to enjoy live music and of course a pumpkin flavored ale magically appears during this time of year. 

 

Oktoberfest at Rowdy Hall – This restaurant in East Hampton simply owns the month of October. If you are in the area you should not miss out on their Oktoberfest menu which only happens during this month. 

 

Beach Walks – Guess what? In the off season, you can park anywhere, at any beach and enjoy it. There are plenty of warmer days during the off season for a little picnic on the beach or a nice beach walk with a cooler breeze. 

 

The Sag Harbor Movie Theater – Movie night is what it’s all about in the fall and the Sag Harbor Movie Theater never disappoints. Nothing beats a nice night out in Sag Harbor with an evening at the theater and a stroll through town in sweater weather!

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TRENDING

The Hamptons’ biggest family event returns to the Children’s Museum of the East End (CMEE) as it hosts the 16th Annual Family Fair. This year’s theme—Endless Summer—promises a joyful morning filled with arts & crafts, water play, live entertainment, food trucks, candy, and more.

16th Annual Family Fair to Benefit CMEE Returns July 18

The Hamptons’ biggest family event returns to the Children’s Museum of the East End (CMEE) as it hosts the 16th Annual Family Fair. This year’s theme—Endless Summer—promises a joyful morning filled with arts & crafts, water play, live entertainment, food trucks, candy, and more.

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Over the past week, there were 25 Listings that went into contract from Westhampton to Montauk.




Compared to this same week last year (2025), there were 25 Listings that went into contract, which is NO CHANGE, year over year.




This same week in 2024, there were 30 Listings that went into contract.

Compared to this past week, there was a DECREASE of 17%.

Hamptons Real Estate Market Data – Week of 7/​7/2026

Over the past week, there were 25 Listings that went into contract from Westhampton to Montauk.

Compared to this same week last year (2025), there were 25 Listings that went into contract, which is NO CHANGE, year over year.

This same week in 2024, there were 30 Listings that went into contract.

Compared to this past week, there was a DECREASE of 17%.

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East Hampton Village and The Baker House 1650 share a similar story - a generational escape, shaped with respect, and elevated by modern comfort.




Every inch of the property is an homage to the timeless luxury of life in the Hamptons - an invitation to stillness. There is no gimmick or kitsch; it is simply a venerated space with an enviable vantage for experiencing East Hampton Village. Credit the state-of-the-art spa for why the boutique hotel looks so chic at age 376. The perfect destination to revitalize after a long day on the beach or night at the Talkhouse.

An Emblem of East Hampton Elegance, Baker House 1650

East Hampton Village and The Baker House 1650 share a similar story – a generational escape, shaped with respect, and elevated by modern comfort.

Every inch of the property is an homage to the timeless luxury of life in the Hamptons – an invitation to stillness. There is no gimmick or kitsch; it is simply a venerated space with an enviable vantage for experiencing East Hampton Village. Credit the state-of-the-art spa for why the boutique hotel looks so chic at age 376. The perfect destination to revitalize after a long day on the beach or night at the Talkhouse.

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  • We visited Gigi’s at Gurneys to check out what’s on the menu this summer. Looking for fresh fish and lobster with sublime views of the ocean? Run, don’t walk.
@gigismontauk @gurneysresorts
  • Last week, Stacey Bendet held a stunning poolside celebration at her Watermill home, signaling the official start of the summer season. DJ Jordan Emanuel from Bravo’s Summer House kept the energy high while guests sipped on LALO cocktails and Wölffer’s iconic wines. Guests were treated to custom bikini charms by Dorne, lymphatic massages, games of beer pong, and a Farmers Daughter pop-up.⁠
⁠
Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#hamptons #aliceandolivia #summer #poolside
  • There are restaurants that simply serve a meal, and then there are restaurants that create an unbelievable memory and experience. Lulu Kitchen & Bar in Sag Harbor is the latter. I recently stopped in for lunch with my co-worker, Val, and from the moment we walked through the door, it was clear why this has become one of the Hamptons’ most celebrated dining destinations.

One of Lulu’s defining features is its commitment to wood-fired cooking. Nearly everything is prepared over a live fire using actual wooden logs, giving the food a distinctive depth of flavor that is difficult to replicate. You can actually see the flames working behind the scenes, adding to the experience.

Lulu also features a fantastic bar with an impressive selection of local craft beers alongside outstanding international offerings, making it just as appealing for an afternoon drink as it is for a full meal.
  • @fellinicoffee pop-up at the @themaidstonehotel serving delicious coffee Friday through Sunday ☕️

#fellini #coffee #easthampton #summer #popup
  • Discovering incredible artists and inspiring artwork at the Hamptons Fine Art Fair. 🎨✨ 

From stunning contemporary pieces to unforgettable creative talent, this is a must-visit for any art lover. 
On view now through July 12. #fineart #art #artist #hamptons
  • Stopped by at @themontaukgeneral where we talked to the owner @kidiament about the stores best selling merchandise
#Matcha #montaukgeneralstore #hamptons
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