Embrace the Fall Season on Long Island: Your 2025 Guide to Autumn Activities

Danielle Speciale • September 18, 2025

Fall on Long Island 2025: Best Pumpkin Picking, Festivals & Things to Do

Fall on Long Island is a season like no other. As the air turns crisp and the leaves burst into brilliant shades of orange, yellow, and red, families and friends alike head outdoors to soak in all the beauty and excitement autumn has to offer. Whether you’re searching for pumpkin picking on Long Island, enjoying cozy farm stands, or looking for the best fall festivals Long Island 2025 has to offer, there’s something here for everyone.



In this updated guide, we’ll share the top things to do on Long Island this fall so you can make the most of the season.

Apple and Pumpkin Picking on Long Island


No fall season is complete without a visit to a local orchard or farm. From apple picking in the North Fork to pumpkin patches across Suffolk and Nassau, these classic activities are perfect for families, couples, or even a fun friends’ outing.


Top Picks for 2025:


  • Harbes Family Farm (Mattituck) – Known for its apple orchard, corn maze, and fresh cider donuts.
  • Wickham’s Fruit Farm (Cutchogue) – Historic farm with beautiful apple orchards.
  • Schmitt’s Family Farm (Melville) – A popular pumpkin picking spot with hayrides and fall fun for kids.
  • Fink’s Country Farm (Wading River) – Great for pumpkin picking, hayrides, and farm animals.


Pro Tip: Weekends are busy, so plan to arrive early for the best selection and parking!

Long Island Fall Festivals 2025


The fall season brings a calendar packed with festivals celebrating food, music, and community. These Long Island fall events are must-visits for anyone wanting to embrace the season.


Don’t Miss These Events:


  • Oyster Festival in Oyster Bay (October 19–20, 2025) – The East Coast’s largest waterfront festival featuring local food, live music, and family entertainment.
  • PumpkinFest at Hicks Nurseries (Westbury, September–October) – Perfect for families, with pumpkins, treats, and fall décor shopping.
  • Riverhead Country Fair (October 12, 2025) – Arts, crafts, local food vendors, and live music in downtown Riverhead.
  • Montauk Fall Festival (October 11–12, 2025) – Seafood, Oktoberfest beer, and live entertainment at the “End” of Long Island.
  • Port Jefferson Scarecrow Walk (October 6 - November 10) - View Scarecrows decorated by local businesses, community groups, and non-profits on East Main Street. The Port Jeff Harvest Festival will be on October 18th and 19th.


Seasonal Fall Activities on Long Island


Beyond pumpkins and festivals, fall is the perfect time to explore Long Island’s natural beauty and seasonal experiences.


  • Fall Foliage Drives – The North Fork wine country and Route 25A offer some of the best views.
  • Haunted Houses & Ghost Tours – Long Island is home to historic mansions and spooky attractions that come alive in October.
  • Wine Tasting Tours – Local vineyards like Bedell Cellars and Pindar Vineyards offer seasonal wines paired with stunning autumn backdrops.
  • Farm-to-Table Dining – Many Long Island restaurants incorporate fresh, seasonal harvest ingredients into their fall menus.

Tips for Enjoying Fall on Long Island 


  • Dress in layers: The mornings can be chilly, but afternoons often warm up.
  • Bring cash: Many farms and vendors still prefer cash over cards.
  • Check event calendars early: Popular events sell out quickly, so grab tickets ahead of time.
  • Capture the moment: Fall foliage and pumpkin patches are perfect backdrops for seasonal photos.
  • Local Chambers of Commerce: Don't forget to check your local chamber of commerce events calendar on their website. There are so many Town & Village events happening this fall and we've found by going to your chamber, you'll help to support local businesses in your area!


Make the Most of Fall 2025


From pumpkin picking and apple orchards to fall festivals and foliage drives, Long Island offers countless ways to celebrate autumn. Whether you’re looking for family fun, romantic weekend plans, or unique seasonal events, fall 2025 is the perfect time to explore all that the island has to offer.


So grab your sweater, order a hot cider, and start planning your Long Island fall adventures today!

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