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Hamptons.com
September 27, 2022

10 Reasons Why the Hamptons is Awesome in the Fall

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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LOCAL EVENTS

Events

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Hampton Jazzfest & LTV Studios Present Bill O’Connell

August 25 @ 06:00 PM - August 25 @ 08:00 PM
LTV Studios 75 Industrial Road Wainscott, NY, 11975
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Hamptons Jazzfest & LTV Studios Present: The McIver Piano Jazz Series

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75 Industrial Road, Wainscott, NY, 11975
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The Perlman Music Program Alumni Octet

August 25 @ 06:00 PM - August 25 @ 07:00 PM
Jewish Center of the Hamptons, 44 Woods Lane, East Hampton, NY 11937
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The Center at West Park Presents One-Night-Only Staged Reading of All the President’s Men

August 25 @ 07:00 PM - August 25 @ 10:00 PM
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A Miserable Evening with Jackie Hoffman at Bay Street Theater

August 25 @ 08:00 PM - August 25 @ 10:00 PM
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Edwina von Gal Receives LongHouse Visionary Award

Edwina von Gal Receives LongHouse Visionary Award

  • @wagsandwalks @themontaukbeachhouse 

Puppies + Pilates + @montaukila = The Perfect Day

Check out our Events Calendar for more events! (link in bio)

#wagsandwalks #animaladoption #adoptdontshop❤️ #dog #montauk #montaukbeachhouse #montaukila #pilates
  • Check out the Top Hamptons Events This Weekend! ⁠
⁠
✨ 50th Annual Hampton Classic Horse Show⁠
📅 Sun, Aug 24 – Sun, Aug 31, 2025 | 8am–5pm⁠
📍 240 Snake Hollow Rd, Bridgehampton, NY⁠
🐴 One of the largest outdoor horse shows in the U.S., a premier summer destination for competitors & spectators.⁠
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🎶 Apollo in the Hamptons⁠
📅 Fri, Aug 22, 2025 | 6pm⁠
📍 Si Si, 295 Three Mile Harbor Hog Creek Rd, East Hampton, NY⁠
Experience the essence of the legendary Apollo Theater with DJ Cassidy, Doug E. Fresh & more!⁠
⁠
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🦈 50th Anniversary of JAWS Celebration – Montauk⁠
📅 Sun, Aug 24, 2025 | 12pm–7pm⁠
📍 Shark Bar Montauk, 2167 Montauk Hwy⁠
Screening, live music with Molly Scheider, themed cocktails, shark merch 🦈 — all to benefit Hayground School.⁠
⁠
⁠
😂 Chelsea Handler at WHBPAC⁠
📅 Fri, Aug 22, 2025 | 8pm⁠
📍 WHBPAC, 76 Main St, Westhampton Beach, NY⁠
A night of comedy with Chelsea Handler!⁠
⁠
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🎵 The Knocks at Surf Lodge⁠
📅 Sat, Aug 23, 2025 | 4pm⁠
📍 The Surf Lodge, 183 Edgemere St, Montauk, NY⁠
The Knocks bring their signature groove to the Hamptons.⁠
⁠
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🌅 Generation S.O.S – Live From Water Mill Fundraiser⁠
📅 Sun, Aug 24, 2025 | 5pm–8pm⁠
📍 Water Mill, NY⁠
Featuring Jason Biggs, Luke K, & MC Sophie Sumner.⁠
⁠
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🇬🇷 Mykonos Nights at Calissa⁠
📅 Fri, Aug 22, 2025 | 10pm⁠
📍 Calissa, 1020 Montauk Hwy, Water Mill, NY⁠
End-of-summer vibes with DJs, drinks & dancing.⁠
⁠
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👜🐶 Bark Jacobs by Marc Jacobs at The HUB⁠
📅 Sat, Aug 23, 2025 | 11am–7pm⁠
📍 The HUB, 2183 Montauk Hwy, Bridgehampton, NY⁠
Shop Marc Jacobs & get your pup’s portrait or initials hand-painted on your accessories.⁠
⁠
⁠
🐾 Wags & Walks’ Party Cruise⁠
📅 Sun, Aug 24, 2025 | 3pm–5pm⁠
📍 Easy Breeze Cruises, 462 W Lake Dr, Montauk, NY⁠
Cruise Montauk waters with cocktails & adoptable pups.⁠
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🎨 5th Annual Celebrating Creatives of Color⁠
📅 Sat, Aug 23, 2025 | 11am–5pm⁠
📍 The Church, 48 Madison St, Sag Harbor, NY⁠
Showcasing artists & authors of color, with works available for sale.⁠
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Check out more events at Hamptons.com (Link in Bio)⁠
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#hamptons #weekend #hamptonsclassic #jaws #montauk #apollotheater⁠
  • The Southampton Animal Shelter Foundation held its “Sweet 16th” Unconditional Love Gala, a premier Hamptons event celebrating compassion, community, and animal welfare at a private estate in Bridgehampton. The Unconditional Love Gala is SASF’s largest fundraiser of the year, with proceeds directly supporting the shelter’s mission to provide care, rehabilitation, and forever homes for homeless animals. ⁠
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Check out the full gallery at Hamptons.com (Link in Bio)⁠
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#animalshelter ⁠
#fundraiser #hamptons #southampton
  • Make sure you check out the sunset music series before the end of August. For more info on dates and times check out the Wölffer website.

#sumsetmusic #winestand #wölffer #rosé
  • Hilary Matt Interiors is a residential design firm started and located in New York City with projects spanning across the country, including in the Hamptons and East End.⁠
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Hilary, principal and founder, is known for a bold aesthetic that is comfortable and livable. She always keeps her clients at the forefront so they can express themselves as individuals through their spaces. After starting out in the fashion industry, Hilary felt a call to interior design where she has been bringing her unique approach and style to every space as the brand continues to grow.⁠
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Hilary spoke more about her background, how each HMI project differs from one another, and why the Hamptons is such a special place to her. She also shared her top 5 interior design tips as inspiration.⁠
⁠
Can you discuss your background and how you got started with interior design?⁠
⁠
HM: I studied business and apparel merchandising. After graduating, my first job was at a women’s contemporary showroom in NYC. I had always loved fashion and wanted to be in the industry. After a year, I realized it wasn’t quite what I expected. I had always been interested in interior design, so I took a leap of faith and accepted a job as an assistant to an interior designer. I was initially nervous to leave fashion, but I figured I could always return. I ended up loving it and worked with her for eight years, learning the ins and outs of the business. I also took classes on weekends and evenings to learn computer programs, scaling, and other essential skills. After leaving that position and having my first son, I started my own company, which has snowballed into what we are today.⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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#hilarymatt ⁠
#hilarymattinteriors ⁠
#hamptons ⁠
#interiordesigner⁠
#hamptons lifestyle⁠
#interiorstyling⁠
#design
  • Comedian Des Bishop took the stage at Westhampton Beach Performing Arts Center this week and delivered laugh after laugh. A native New Yorker, Des moved to Ireland in his teenage years, which ultimately inspired his start in comedy and a successful career that has spanned three decades.⁠
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His comedy is full of observational humor and nostalgia, whether it be about his many cross-cultural experiences, an ever-changing societal landscape, and his own personal stories growing up. Des brings energy and a unique perspective to every show, evident at his Westhampton show, the place he has spent all his summers since the 90s.⁠
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Des spoke more about his background, how his experiences have shaped his approach to comedy, his connection with the East End, and his WHBPAC show.⁠
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Can you tell us a bit about your background and how you first got into comedy?⁠
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DB: Well, my background is a little complicated, but the quick version is I grew up in Queens, flunked out of St. Francis Prep at 14, and ended up going to Ireland to boarding school in 1990. It was a crazy, life-changing experience, but it definitely saved my education and ultimately inspired a comedy career that in the early days focused a lot on being an outsider looking in. It’s hard to know if I ever would have tried stand-up if I hadn’t been in Ireland. I got sober at 19 and it was a comedian I knew from that world that pushed me to try stand up. Once I got on stage that was all she wrote. I was addicted.⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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#desbishop #comedy #westhampton #whbpac
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