This Under-The-Radar New York Destination Is A Celebrity Refuge That Comes Alive With Vibrant Fall Foliage

There's an underrated celebrity paradise in Southhampton, Long Island. Home to ornate celebrity mansions, fresh farmer's markets, and some of the most vibrant fall foliage in the United States, Water Mill should be at the top of your fall travel itinerary. Water Mill is small-ish village with a population of around 2,500 and a history going back to the 1600s.

While many flee to the Hamptons in the summer to escape the scorch of New York, fall is when this area really comes alive. Visit the Long Island region later in the year and you will see the trees transform, their leaves turning shades of red, orange, and pink. Water Mill is also home to impressive architecture, so take a drive around town to see what you might find. 

There are a few luxury hotels nearby, including A Room at The Beach, a highly rated leafy resort where rooms start around $300 a night in the off-season at the time of writing; the opulent 1708 House, where rooms are half the price; and a selection of other luxurious and mid-range hotels in Southampton. New York City is around 95 miles from Water Mill, and it takes anywhere from 90 minutes to two and a half hours to drive there, depending on traffic. You can also catch the No. 38 bus from 40th & Lex to Water Mill. The bus is direct, arrives more or less every half hour between 8 a.m. and 11:30 p.m., and takes around two hours. If you want something a bit cheaper after visiting Water Mill (it is the third most-expensive zip code in the U.S., after all), then check out New York's more affordable alternative to the Hamptons.

AFAR magazine suggested in 2024 visiting Water Mill between November 4th and November 11th for the best fall foliage views. Fall foliage dates aren't precisely consistent year to year, so to make sure you track down the very best autumnal views, consider following I Love NY's weekly fall foliage report or consulting a number of fall foliage finder apps. I Love NY's report tracks the state's changing leaves week to week to help visitors plan their trip to get the best fall views.

Soak up those autumnal vibes with a visit to Pumpkintown. Open from early September until the end of October, Pumpkintown has 30 acres of farmland where you can pick pumpkins and apples, go on a wagon or tractor ride, race (plastic) ducks, get lost in a giant corn maze, learn how to milk a cow, and buy autumnal snacks like apple cider donuts, caramel apples, and hard cider made from local apples.

Pumpkintown is open from 9:30 a.m. to 5:30 p.m. It costs $24 per person on holidays and weekends to explore the full farm and all its activities, and $17 during the week. Pets and outside food are not allowed on the farm. There is also a cute winery in town called Duck Walk Vineyards just across the street, so stop by for a wine tasting and some cheese.

Water Mill has been known to attract celebrities and public figures, and Jennifer Lopez, Anthony Scaramucci, Richard Gere, and the Hilton family each currently or formerly owned property in the village. While you could take a self-guided walking tour of all the rich people's homes, it might be a better use of your time to turn those eyes to Water Mill's Parrish Art Museum. This museum houses over 3,500 works of art, including landscapes, impressionist work, and sculptures predominantly by people who lived in or were influenced by the Long Island area.

While you can certainly visit year-round thanks to Water Mill's wonderfully diverse landscape, the town is even more striking in the fall. Exploring this area between September and November will take you to farmland, woods, nature preserves, and viewpoints where you can gaze out at the autumnal colors making their way across the leaves.

Scenic places to explore include Tuckahoe Hill Preserve, where you can wander through quiet meadows and past trees as you share silence with the local deer and turkeys. Or head to the short, mile-long Long Springs County Park loop through the woods and feel the leaves crunch under your feet. For more activities on Long Island, Port Jefferson offers interactive museums and several parks perfect for a hike.