We like to leave New York City and head out east to the Hamptons to explore some of the best things. Peak season is over and you wouldn’t realize it, but the best time to go is in the fall when it’s a lot quieter. They. have the best beaches, best restaurants, wine tastings and some of my favorite things to do in the fall season. You can bring the whole family or go for a romantic weekend getaway on the east coast. An easy trip on the Hampton jitney or Long Island Rail Road from Penn Station, it’s the perfect spot to escape for New Yorkers in early fall. Here is our ultimate guide to delicious food, historic charm and real life in the Hamptons this season.
Located in Water Mill, this U-pick orchard is one of the very best! They are great at announcing on their Facebook which product to look forward to and now that it’s apple picking season, this is at the very top of our list!
You can’t go out east and not go to Wölffer, I don’t make the rules! This is the ultimate winery experience and is perfect for a romantic getaway or a girls weekend activity. Located in Sagaponack, the vineyard also has non alcoholic options on top of the best wine and cider around.
Beach Day
No matter where you stay out east, there are tons of beaches around. My unpopular opinion is that the beach is great in the fall. I do love to go in a light sweatshirt and watch the waves crash during a sunrise or sunset. Even during the day, it’s nice to sit and read under the sun while there’s a nice breeze.
This top hotel in Sag Harbor is so much more than just a place to stay. The food is exceptional, they have a spa and constantly a ton of activities to offer. You could stay there the whole time and not explore the Hamptons and be totally fine if you wanted! With a tennis court, lawn yoga and a fall wine dinner series, why stay anywhere else?
This delicious Italian spot has locations all over the Hamptons. It’s incredibly authentic and the bread is what dreams are made of. I always recommend their coffee to anyone who goes for lunch, too. But the pasta is the main event!
With locations in Amagansett and East Hampton, you can check out this farm market and shop all over! They have over 60 crops, herbs, grains and flowers to check out and the artisanal foods at the market are a crowd pleaser. Fresh produce, pastries, seasonal specialties and so much more!
There are few things more fun than checking out cute little boutiques, getting brunch and having a laid back day. When the breeze starts showing up in the fall, all I want to do is stroll with a coffee and get new sweaters. We love coming here because it’s a great way to spend the day and feel relaxed.
This spot has several locations all over the Hamptons, but it’s a must go! They have the yummiest bites in town and it’s a local spot that makes for a great breakfast. Make sure to try their golden pear muffins!
This East Hampton experience has so much to see. We love going here for a nice quiet walk through nature. The best part is that they always have something really cool going on here. Art and exhibitions, educational tours, workshops and so much more.
We typically end a long weekend in Montauk at some point. This state park is an oasis to see the outdoors, fish, have a quiet day on a rocky beach and just ultimately relax. You can bring a dog as long as it’s on a leash!
If there’s one brunch I can offer you, it’s this! It’s in the center of the Hamptons and is actually a hotel you can stay at. The place is beautiful and we often go for a nice brunch or breakfast. The food is incredibly fresh and it’s just a nice, relaxing place to be. People even get married here!
This Montauk tradition is a must-go. They have some of the very best lobster rolls around and not only are they a bar and restaurant, but they also have a hotel. It’s a great place to watch a sunset with a drink in hand for the transitional season.
Located in Water Mill, we go every single fall! In my opinion, this is the best place to get pumpkins. We love how family-friendly they are and they have so much stuff for the kids to do. Beyond pumpkin picking, you can play games, go on a tractor ride, check out the maze park, get apple cider donuts, caramel apples, pastries and so much more! This is a great morning or afternoon activity.
Rogers Mansion
Finally, located in Bridgehampton, this haunted mansion is available for tours. There’s something about fall that screams spooky season and with Halloween around the corner, this is a spooky activity you can check out! The place has been restored and opened back up to the public, so now you can go ghost hunting.
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