Autumn on Long Island is truly enchanting. As a cool breeze sweeps across the coasts and leaves turn to shades of red and gold, Long Island is filled with an array of seasonal activities and events. Whether you’re looking to explore LI’s rich history against a scenic backdrop, take in the vibrant foliage, or enjoy the season’s harvest, fall on Long Island has something for everyone.

Here’s our guide for things to do on Long Island in the fall.

 

Take in the fall foliage

Fall Foliage Old Bethpage

From lush parks to scenic waterfronts, here are some stunning spots to take in the fall foliage and beauty of fall:

 

Attend a festival

Apple festival

A range of food festivals are coming up this season on Long Island, showcasing local cuisine and seasonal specialties. Here are some festivals worth checking out this autumn:

 

Go pumpkin and apple picking

Pumpkin Picking

Whether you leave them on your porch on display all season, or carve a funny face for Halloween, pumpkins are a must-have fruit of harvest. Here are some places to pick:

Apple picking is another staple of fall here on Long Island. Head out to the East End some time this fall and pick your own from one of these spots:

 

Vineyards & Views

North Fork Lieb Cellars grapes

Fall is the perfect time to explore the North Fork’s picturesque vineyards, where the autumn foliage creates a stunning backdrop for a day of wine tasting. Enjoy the crisp air as you sample award-winning local wines and take in the breathtaking views of the colorful vineyards. Although Long Island Wine Country boasts 75+ distinct wine producers, consider these five favorites for a one-day vineyard-hopping itinerary:

Learn more about Long Island Wine Country here.

If beer and cider is more your style, Long Island has plenty to offer. With a thriving craft brewery scene, sip on a local brew and soak up the autumn colors. Here are some must-visit breweries/cideries to complete your boozy Long Island fall:

 

Explore LI's rich history and admire Gatsby-era architecture

Oheka in fall

2025 is the 100th anniversary of F. Scott Fitzgerald’s iconic novel, The Great Gatsby, which was inspired by the luxurious Long Island living of the early 20th century. The Gold Coast is home to the opulent estates once owned by New York’s elite.

Sprawling over 200 acres, visit Old Westbury Gardens and admire the carved wood architecture, sweeping lawns and beautiful formal garden.

Kevin Jonas and his wife Danielle famously wed in Long Island’s Oheka Castle, a turn-of-the-century French-style chateau now turned hotel, event venue, and restaurant.

Sand’s Point Preserve is home to three spectacular mansions: Falaise, Hempstead House, and CastleGould.

Long Island played a significant role in early American history, including key events during the Revolutionary War, and is home to numerous colonial homes and historical landmarks. Pick a weekend to check out George Washington’s Spy Trail, with sites including Sagtikos Manor and Stony Brook Village Center.

The region also boasts a rich marine and aviation history, from early whaling in ports like Sag Harbor to the pivotal role LI-based company Grumman had in aerospace innovation. Visit the Cradle of Aviation Museum and New York State’s oldest lighthouse, the Montauk Point Lighthouse Museum.

 

See a show

John Engeman Theater

The vibrant theater scene comes alive with a diverse lineup of performances that promise to entertain and inspire.

Live theater:

Concerts:

 

Set sail for sightseeing and seal watching

Seal Watching

Water activities don’t end come fall! Set sail through autumn onboard Easy Breeze Cruises and experience breathtaking ocean views of Montauk.

Catch a buzz with some buddies while on the Tiki Boat this fall. Book the sunset cruise tour for the most gorgeous view of the sun over the water.

Autumn and winter are Long Island’s seal watching seasons, beginning in November. Either watch for seals on the shore with a Seal Walk, or head out on the water on a Seal Cruise with the Coastal Research and Education Society of Long Island, CRESLI.