Top 6 Fall Activities on Long Island

Some folks say the sidewalks roll up after Labor Day and that there’s just no action on the East End after the summer season. We challenge these naysayers and want to tell everyone what fall on the East End of Long Island is all about!



  1. Indian Summer is all around us and there is no denying some of the best beach weather is still to come. Autumn brings bright blue skies, dry air and a tranquil beach. Follow the tranquility with a perfect sunset and let’s just say heaven can wait! We love fall strolls on the bay water beaches of Shelter Island, collecting beach glass and stealing the last dip before winters temperatures turn a swim into polar bear competition.
Long Island Sunset
  1. Apple Picking! Farms are bountiful out east, but the apple orchards are some of the best NY State has to offer. We love apple picking on the South Fork & North Fork of Long Island, but one of our favorites is the Milk Pail on the shores of Mecox Bay. Once you taste a fresh picked apple from here, you are spoiled forever and will crave these local delectable treats. We are talking about award-winning apples in a beautiful orchard, ever so close to the sea. Owned by the Halsey family since1640 and still family run by the 12th generation. The history speaks for itself here and the farm stand is also flush with cider doughnuts, just sayin…
apple-picking on Long Island
  1. Tour the Montauk Lighthouse! This world famous lighthouse is located at the tip of eastern Long Island with 360-degree views of the Block Island Sound & Atlantic Ocean. Constructed in 1792, it is the oldest lighthouse in New York State and still serves as a navigation aid. Flush with history, the museum is located in the “keepers” house and has an assortment of historical documents and photographs. For the thrill seekers, an opportunity to climb the 137 iron steps to the lighthouse tower 110 feet high is a must!
montauk-lighthouse on Long Island
  1. Farm Adventures – For one stop farm action you can’t go wrong with Harbes Family Farm and Vineyard for family or adult fun. Complete with a farm stand market and bakery, a 10-acre ‘Barnyard Adventure’ Park, Harbes Vineyard’s Tasting Room, 2 pumpkin patches, 2 Corn Mazes for day and night adventures, Hayrides, Gem mining, Pig races and more. Don’t forget to try the kettle corn!
Pumpkin Patch- a favorite fall activity on Long Island
  1. Hiking amongst the Fall Foliage – Prefer orange, reds, and yellows to green leaves? With over 200 miles of hiking trails on Long Island ranging from easy to adventurist there are several choices. Beauty aside we love the convenience of the Mashomack Preserve right here on
 Shelter Island.  
There are 11 miles of easy hiking trails that run through the oak woodlands, marshes, ponds, and creeks. Keep an eye out for osprey, ibis, foxes, and terrapins. Mashomack Preserve offers a great visitors center and an indoor bird watching window for birding enthusiasts. Check their schedule for guided tours and night walks. For those willing to adventure a bit further, check out the The Paumanok Path, a 125-mile trek through wilderness, with rolling hills with panoramic vistas, sand dunes, coastal ponds, and all things nature.
Couple hiking through the fall foliage
  1. Seal walks with CRESLI at the Cupsogue Beach County Park – These harbor seals are dangerously cute and who doesn’t want to see these aquatic mammals up close in their natural habitat? Seal walks are approximately 1.2 miles round trip, lasting about 1-2 hours and suitable for children. Long Island’s seal species typically included Harbor and Grey Seals, which are relatively abundant in our waters from late, fall until late spring.  The weather can be surprising here, i.e. cool and wet so appropriate dress or a change of clothes for after your walk is highly recommended.
Seal walks on Long Island

Join us this fall at Shelter Island House and try some of these exciting fall activities for yourself! The weather is divine and the crowds are finally thinning out!