While summer may be the Hamptons’ signature season, here’s the best-kept secret: the real magic starts when fall rolls in. With the tourists gone and the traffic jams a distant memory, autumn is the time to savor the East End’s charms at a slower, more enchanting pace. The sun is still warm, the beaches are quiet, and the crispness of the air hints at cozy sweaters and pumpkin patches. What better way to embrace the season than by diving into classic fall activities that capture the region’s unique character? Here’s your guide to experiencing autumn bliss in the Hamptons.
1. The Milk Pail U-Pick Farms
[Photo by Hamptons Social]
Autumn is synonymous with apple picking, and no place does it better than The Milk Pail U-Pick Farms in Water Mill. A family-owned farm that has been part of the Hamptons landscape for over 50 years, The Milk Pail offers more than just apples — it’s a way to immerse yourself in the essence of the season. Rows of apple trees stretch out before you, their branches heavy with fruit. Whether you’re in the mood for a tart Granny Smith or a sweet Honeycrisp, picking your own apples feels like a rite of passage.
But it doesn’t stop at apples. The farm is also known for its picturesque sunflower mazes and its pumpkins and gourds, perfect for decorating your porch or carving into jack-o’-lanterns. On weekends, the farm buzzes with activity as families and friends make their way through the orchards, filling baskets and taking photos. The experience is a throwback to simpler times, a reminder of the charm of farm-to-table living. Before leaving, make sure to grab some freshly pressed apple cider or their sensational apple cider sugar doughnuts from their farm stand — the perfect way to savor your haul. If you stop by the Milk Pail’s additional market location at 1346 Montauk Highway in Water Mill, be sure to sample their refreshing Apple Cider Slushie.
The Milk Pail U-Pick Farm, 50 Horsemill Lane, Water Mill, NY
2. Wölffer Estate Vineyard
[Photo courtesy of Wölffer Estate]
Wölffer Estate Vineyard isn’t just a vineyard; it’s a Hamptons institution. Set amidst the rolling hills of Sagaponack, the vineyard offers an idyllic backdrop for autumn festivities. While it’s famous for its rosé during the summer, fall is when Wölffer truly shines. The vineyard’s Annual Harvest Party on the second weekend in October is the ultimate way to toast to the season. It’s an all-day affair at the estate filled with activities that evoke the spirit of harvest — grape-stomping, barrel-rolling, and hayrides through the golden fields.
On Saturday, October 26th, the Wölffer Wine Stand hosts the Pumpkin and Cider Fest from 1:00 PM to 4:00PM at 3312 Montauk Hwy, Sagaponack, NY 11962. Bring the family for an afternoon of fun with live music, a tasting of our festive ciders, and kids activities including a bouncy house, fall crafts, and a puppet show! Enjoy the crisp autumn air, warm pizza, and relax by the fire pits — all supporting Gimme Shelter Animal Rescue. Tickets are $35 and can be purchased here. Please note, additional food and beverage is not included in the ticket price and will be available for purchase a la carte on-site. All activities are included in the ticket price.
For those who prefer a more refined experience, there’s wine and cider tasting, featuring everything from their crisp chardonnays to the signature Wölffer No. 139 dry ciders. Guests are encouraged to roam the vineyard, glass in hand, as live music fills the air and the colors of the season provide a breathtaking backdrop. The vineyard also offers special pairing menus throughout the fall, with dishes inspired by the harvest, making it a must-visit spot for food and wine lovers alike.
Wölffer Estate Vineyard, 139 Sagg Road, Sagaponack, NY
3. The Baker House 1650’s Afternoon High Tea and Apertivo Sunset Cocktails
This fall, the award-winning property Baker House 1650 brings a touch of English tradition to the Hamptons with its delightful High Tea, making it a must-do activity for those seeking a cozy, luxurious experience. On the first Sunday of each month, from 1:30 p.m. to 4 p.m., guests can enjoy an afternoon of tea, champagne, light bites, and sweet treats, perfect for a relaxing time with friends or family. Be sure to RSVP in advance to secure your spot for this sumptuous affair. Here is the RSVP link. From Thursday to Saturday, The Baker House also hosts elegant Aperitivo evenings from 5 p.m. to 8 p.m., where you can sip on signature cocktails curated by their house mixologist while taking in the beauty of the exquisite property. RSVP here. These events offer the perfect way to unwind and embrace the charm of the Hamptons in autumn.
Baker House 1650; 181 Main Street, East Hampton
4. Marders in Bridgehampton
[Photo by Hamptons Social]
Gardening enthusiasts rejoice — fall is not the end of the planting season. At Marders, a 40-acre garden center and nursery, autumn is when the landscape comes alive in hues of red, orange, and gold. Known for its year-round workshops and events, Marders transforms into a botanical wonderland come fall. Whether you’re a seasoned gardener or a curious beginner, their horticultural workshops provide hands-on learning opportunities, from planting fall perennials to designing your own autumnal flower arrangements. In the autumn, be sure to check their calendar for opportunities to meet rescue Birds of Prey from the Evelyn Alexander Wildlife Center.
The beautiful store is one of the most enchanting places in the Hamptons to shop for gifts from irresistible candles to coffee tables books, nature-inspired toys for children, and unique tabletop creations. There is also a beautiful selection of greeting cards with whimsical artwork and illustrations.
The grounds are a feast for the senses, with towering trees and blooming seasonal flowers creating a tranquil atmosphere. It’s the perfect place to pick up some fall essentials, like tulip bulbs, mums and ornamental grasses, to bring a touch of autumn back home. The customer service is exceptional—staff members are not only friendly but also incredibly knowledgeable. Whether you’re seeking advice on finding the perfect limelight hydrangea tree or learning the best techniques for pruning your roses, they are eager to assist and guide you through every step. Even if you’re not planning to garden, simply walking the grounds is a meditative experience, especially with the fall foliage as a backdrop. Stop by the café for a cup of herbal tea, and spend an afternoon reconnecting with nature.
Marders, 120 Snake Hollow Road, Bridgehampton, NY
5. Stephen Talkhouse
Just because summer is over doesn’t mean the music stops at Stephen Talkhouse. This legendary venue in Amagansett is known for hosting some of the best live music on the East End, and its fall lineup is just as vibrant. Trivia nights, acoustic sessions, and concerts keep the energy high, drawing crowds eager to keep the spirit of summer alive. In fact, the fall vibe at Stephen Talkhouse is one of casual intimacy, where locals and regulars gather to enjoy the music, chat over drinks, and revel in the relaxed pace of the off-season.
Manager Peter Honerkamp’s philosophy of maintaining an “endless roaring party” ensures that every night feels like a celebration. Whether you’re discovering a new local band or dancing to a tribute act, the laid-back, welcoming vibe makes it easy to lose track of time. Grab a drink—like the Talkhouse Encore, the award-winning canned cocktail brand created by Peter’s daughter, Ruby Honerkamp—mingle with the crowd, and let the music carry you through the crisp autumn evenings.
Stephen Talkhouse, 161 Main Street, Amagansett, NY
6. Montauk Farmers Market
End your week with a visit to the Montauk Farmers Market, the largest on the East End. Open every Friday, it’s the place to go for fresh, local produce and a taste of the Hamptons’ seasonal bounty. Stroll through the stands and sample offerings from vendors like The Biscotti Company, Hen of the Woods, and Sag Harbor Honey. From fresh vegetables to artisanal cheeses, the market captures the best of the region’s agricultural heritage.
The atmosphere is lively but relaxed, as locals and visitors alike gather to chat, shop, and enjoy the last of the warm sun before winter arrives. It’s a reminder that even as the seasons change, the Hamptons’ community spirit and love for fresh, local food remain constant. Load up on seasonal favorites like apples, squash, and honey — you’ll leave feeling nourished and ready for whatever the weekend holds.
Montauk Farmers Market, 742 Montauk Highway, Montauk, NY
7. LongHouse Reserve
[Photo courtesy of LongHouse Reserve]
For those who prefer their autumn experiences with a touch of art and culture, LongHouse Reserve in East Hampton is the place to be. This 16-acre garden and sculpture park offers a unique blend of nature and creativity, with pathways that wind through striking art installations and carefully curated landscapes. Visiting in the fall means witnessing the changing colors of the garden, where sculptures peek through trees shedding their leaves, creating a striking contrast.
LongHouse hosts a variety of seasonal events, from Sunday yoga sessions in the garden to guided walking meditations designed to help you breathe in the fresh, crisp air and reset for the week ahead. It’s a place where you can take your time, whether that means exploring the art exhibits, finding a quiet spot for reflection, or joining one of their workshops that blend art with wellness practices. Each visit is a chance to find inspiration and take in the beauty of the season in one of the Hamptons’ most tranquil settings.
LongHouse Reserve, 133 Hands Creek Road, East Hampton, NY
8. Annual Montauk Fall Festival
Fall may officially begin on September 22, but in Montauk, the season doesn’t truly kick off until the second weekend in October. For the past 43 years, the Annual Montauk Fall Festival has been the unofficial start of autumn, bringing locals and visitors together for a celebration of all things seasonal. Picture strolling along the streets lined with vendor stalls offering everything from local seafood to artisanal crafts. The festival is a sensory experience — the scent of clam chowder wafts through the air, mingling with the sound of live music. Families can enjoy classic games, like ring toss and sack races, while adults sip on craft beer and wine from nearby vineyards.
And then there’s the legendary chowder contest, an event that has become a beloved tradition. At 11 a.m. on Saturday, chowder aficionados gather, spoons in hand, to sample and vote on the best local concoction. Whether you prefer your chowder creamy New England-style or a spicy Manhattan variety, there’s something for every palate. This is more than just a festival; it’s a chance to connect with the community and embrace the flavors of fall.
Montauk Chamber of Commerce, 742 Montauk Highway, Montauk, NY
9. Fairview Farm
[Photo courtesy of Fairview Farm @fairviewfarmatmecox]
For a truly immersive fall experience, Fairview Farm’s eight-acre corn maze is a must. As you navigate the two miles of winding paths, it’s easy to feel transported, surrounded by walls of golden corn that tower overhead. The maze is designed to challenge and delight, with hidden paths and fun clues that guide you along the way. It’s a classic fall adventure that appeals to all ages, whether you’re a thrill-seeker or just looking for a peaceful escape from the city.
The farm also offers a variety of other fall activities, including pumpkin patches and hayrides. After conquering the maze, reward yourself at their farm stand, where you’ll find a selection of seasonal pies, homemade jams, and fresh produce. It’s the perfect way to savor the tastes of the season and bring a little bit of the farm home with you.
Fairview Farm, 69 Horsemill Lane, Bridgehampton, NY
10. Peconic Land Trust
[Photo courtesy of the Peconic Land Trust @peconiclandtrust]
Nature lovers and conservationists alike will find plenty to explore at the Peconic Land Trust’s Autumn Open House. Held on October 5, the event is a celebration of the region’s natural beauty, with guided garden tours, birdwatching sessions, and craft activities that make it an ideal outing for families and solo adventurers alike. The Trust’s mission to preserve the natural environment of the Hamptons is at the heart of everything they do, and their events offer a glimpse into their ongoing efforts.
If you miss the Open House, don’t worry — the Trust’s calendar is filled with activities all season long. From guided hikes that showcase the changing leaves to workshops on sustainable gardening, there’s always something to engage with and learn about. It’s an opportunity to not only enjoy the beauty of fall but to connect with the land in a meaningful way.
Peconic Land Trust, 296 Hampton Road, Southampton, NY
11. Hank’s Pumpkintown
[Photo by Hamptons Social]
No fall experience in the Hamptons is complete without a visit to Hank’s Pumpkintown. From apple and pumpkin picking to navigating a corn maze, this place offers every quintessential activity the season demands. Hank’s is the ultimate stop for anyone looking to soak up the spirit of fall and escape the everyday hustle.
Hank’s Pumpkintown, 240 Montauk Highway, Water Mill, NY
12. Amber Waves Farm
Amber Waves Farm is a quintessential autumn destination that offers more than just fresh produce; it’s a full-on experience. Located in Amagansett, this beautiful farm is the perfect spot to embrace the season. Start your visit by picking out the perfect pumpkin or two from their selection. Then, grab a freshly brewed coffee and pair it with one of their delicious homemade muffins or a farm-fresh egg sandwich — it’s the perfect way to fuel up for a day of exploration.
The idyllic grounds are an open invitation for children to play and roam. The farm features charming wooden playhouses, swings, and friendly farm animals like goats and chickens, making it a magical place for kids to connect with nature. On Saturdays, the farm hosts engaging workshops for children, giving them the chance to explore hands-on activities and learn about farm life.
Be sure to check Amber Waves’ website for more events throughout the fall season — from harvest festivals to farm-to-table dinners, there’s always something new to experience as the leaves change and the air turns crisp.
Amber Waves Farm, 367 Main Street, Amagansett, NY
This post was all about the best activities to do in the Hamptons in the autumn.
