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Get Ready for Fall in the Hamptons

Get Ready for Fall in the Hamptons

Hamptons September 21, 2022

Get Ready for Fall in the Hamptons

Exciting autumnal events the whole family will love.
While Hamptons summers are certainly memorable, there is something truly unique and special about the Hamptons in the fall. From savoring cider donuts to taking toddlers to their very first pumpkin patch, there are countless ways to celebrate the season. Here are some top things to do in the Hamptons this fall.

Pumpkin Patches & Apple Picking

Nothing welcomes color-changing leaves and pumpkin spice warmth of fall better than visiting pumpkin patches and going apple picking. Fortunately for Hamptons residents and visitors alike, there are countless options to ring in the fall season.

U-Pick Apples & Pumpkins 2022

Milk Pail Orchard welcomes Hamptons residents and visitors to their farm for the U-Pick Apples & Pumpkins event, where guests pick apples from their trees and pumpkins straight from the vine. They are open Friday through Sunday in September and October, offering free admissions for up to six people with the purchase of a half bushel bag which holds about 20 pounds.
Wander the farm and choose perfectly ripe apples for homemade pies, pumpkins for carving and cooking, and fresh squash to up the ante on holiday meals. You’ll be able to pick from over 60 different pumpkins, gourds, squash, and apples, including Honeycrisp, gala, acorn squash, delicata squash, Milk Pail 25, and many more. Parents can warm up with hot cider and coffee while their kids gather their edible treasures from the adorable and accessible dwarf apple trees. Hours of family bonding over apple picking, pumpkin plucking, and cooking await you!

Hank’s Pumpkin Town

A visit to Hank's Pumpkin Town brings more than pumpkin and apple-picking opportunities — it means hours of autumn-themed entertainment for the entire family. Start your day with a visit to the market for freshly baked cookies, pies, cider donuts, candy apples, and other confections. Don’t forget to stop by the Corn Shed for scrumptious roasted corn!
After enjoying a snack, spend the day picking apples and pumpkins, weave through corn mazes, and enjoy wagon rides, tractor train rides, giant slides, games, and playgrounds. If you want to make lasting memories with loved ones and support a beautiful family farm, add Hank’s Pumpkin Town to your calendar this fall.

Fairview Farm Corn Maze

Get lost and found this autumn in the Fairview Farm corn maze. Wander through eight acres of towering corn, nearly two miles of paths, and two bridges to take in panoramic views of the surrounding lush farmland, Mexico Bay, and the Atlantic Ocean. Admission costs a few dollars, with tiny tots three years and younger admitted for free. Fairview Farm provides so much more than a corn maze, allowing your family to test their aim at the corn cannon, pick some pumpkins, and nosh popcorn and ribbon fries at the concession stand.

Ghost Hunting At The Southampton History Museum

With bravery in your heart and a childlike sense of wonder, join the Long Island Paranormal Investigators for an exclusive tour of the Rogers Mansion and Halsey House during the annual ghost hunting. As you make your way through the Rogers Mansion walk-through exhibit, you’ll sense ghosts and ghouls around you as you learn about the history of Southampton whaling captain Albert Rogers. For a real fright, book a private investigation of the Halsey House, where the Investigators shed light on the mansion’s lingering inhabitants.

Hamptons International Film Festival

The annual Hamptons International Film Festival is a highly anticipated event, with this year’s festival featuring ten days of captivating films spread out over two weekends. HamptonsFilm started the festival in 1992, sharing the beloved art of film via various international films and filmmakers. This treasured nonprofit organization hosts year-round screenings of global narratives and documentaries, educational programming, a one-of-a-kind Screenwriters Lab, and educational initiatives that provide invaluable exposure for filmmakers. Opening night is Friday, October 7, so mark your calendar!

Montauk Chamber Of Commerce's 41st Annual Fall Family Festival

Brought to you by the Montauk Chamber of Commerce and Visitors Center, you won’t want to miss the Montauk Chamber of Commerce 41st Annual Fall Festival on October 8th and 9th. This autumn jubilation offers a multitude of exciting family-friendly experiences that highlight the majesty that is Montauk in the fall. Dance the night away in the gazebo to live music, participate in the silent auction, and delight in sweet and savory treats at the food tent. While adults enjoy tasty eats and live entertainment, little ones partake in pumpkin painting, crafts, bouncy rides, street painting, and more.

Wag-O-Ween Spooktacular

What better way to celebrate Halloween and show your community pride than submitting your jack-o-lantern-dressed pup to a costume contest? Head to the 4th Annual Wag-O-Ween Spooktacular on Saturday, October 22, to support the Southampton Animal Shelter Foundation. Pack the car with kids and canines and prepare for a fun-filled day of activities and contests for all. Deck your children and fur children out in their spookiest costumes to compete in the Kiddie Costume Contest & Parade and the Doggie Costume Contest & Parade. Be sure to stop by the Howloween Photo Booth to snap some pics for your family photo album! Additional activities include games and prizes, face painting, and a chance auction. There will also be plenty of baked goods, dog costumes, and dog toys for sale!

East Hampton Village Fall Festival

During the last week of October, locals and visitors gather for the highly coveted East Hampton Village Fall Festival. The East Hampton Chamber of Commerce curates an exciting and entertaining celebration of the Hamptons in October. The festivities encompass a myriad of local businesses, artists, eats, crafts, and nonprofit organizations. Everyone gathers to rejoice in the East Hampton community and bask in the diversity of local businesses and their unique offerings. While parents and empty-nesters enjoy live music and shopping, children romp around the Kidzone, where they paint pumpkins, create science and art projects, climb the climbing wall, participate in the costume parade, and additional holiday-related amusement.

Light The Lighthouse

People of all ages look forward to the annual Light the Lighthouse event, bringing locals from fall to winter with various festivities. Commissioned by Congress during George Washington’s presidency, this event is full of light and love as it is history. The lighting ceremony of the Montauk Lighthouse boasts a beautiful display of holiday decorations strewn about the lighthouse, with some festive music, hot cocoa, and snacks to boot. This is a can’t-miss community event, especially since the Lighthouse is a nonprofit entity dependent on donations to fund the annual holiday lighting.

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