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Insider’s Guide to Catching Long Island’s Fall Splendor

September 22, 2022

Autumn in the northeast is unlike any other region in the United States. As the days shorten and temperatures drop, the leaves begin to change from green to yellow, orange, and red, creating a beautiful array of colors that cannot be missed.

There are dozens of places across Long Island that showcase the colorful foliage as you stroll through the gardens of mansions and arboretums or gaze in awe at the falling leaves of the many trails of our parks and preserves as you hike or bike through. These Instagram-worthy settings are sure to please the senses and that’s why we’ve put together this insider’s guide to catching Long Island’s fall splendor this autumn.

To discover where you BeLong this Autumn, see our full list of Fall Festivities & Seasonal Specials on Long Island.

North Shore

The North Shore is a gold mine for finding nature preserves, sanctuaries, county parks, state parks, bike trails, farms, mansions, and historic sites. The go-to region for scenic fall excursions, the hilly landscapes and miles of trees provide for picturesque fall views that are Instagram-worthy.

Planting Fields

  • Old Westbury Gardens: Located on an elegant estate featuring a sprawling formal garden over 200 acres, this spectacular mansion in Old Westbury is surrounded by fall foliage and autumn colors.
  • Caumsett State Park: Offering miles of walking, hiking, AND biking trails in Lloyd Neck that are ideal for spotting the changing of the leaves and a variety of indigenous wildlife, history buffs will be pleased to learn that the historic Henry Lloyd Manor House built in 1711 still sits on the property.
  • Planting Fields: Featuring 409 acres of greenhouses, rolling lawns, formal gardens, woodland paths, and an outstanding plant collection, Planting Fields is a magnificent Gold Coast estate from the 1920s in Oyster Bay that is perfect to roam and take in the imagery this fall.
  • Sands Point Preserve: Home to three spectacular mansions, Falaise, Hempstead, and Castle Gould, the preserve’s green centerpiece is the Great Lawn. With more than 200 acres of natural and landscapes areas, Sands Point offers six marked hiking trails that weave through woods, scenic cliffs, gardens, and a freshwater pond with views of the Long Island Sound.

North Fork

With a combination of mature trees and meadows as well as a mix of fresh and saltwater wetlands, the North Fork has some of the most scenic trails on Long Island from preserves to county parks that offer access to the Long Island Sound.

Credit: Downs Farm Preserve/Town of Southold/Website

  • Sound View Dunes Park: Located in Peconic with 57 acres of beach, dune, wetland, and forest habitat, the trails at Sound View Dunes offer stunning views of the Long Island Sound with the Beach Trail providing a leisurely hike and the Forest Trail providing a more challenging option.
  • Downs Farm Preserve: Explore Cutchogue’s 51-acre parcel of land with miles of trails that adjoin farmlands and the tidal wetlands of Downs Creek. The National Historic Landmark has the perfect scenic routes for catching the fall splendor of the North Fork.
  • New York State Bicycle Route 25: For the ideal biking path with 67 miles of road, Route 25 connects to the EPCAL bike path and runs from Smithtown east to Orient Point, diverging off Route 25 in parts of Riverhead and Aquebogue and also connects with Route 48 in Southold.
  • Laurel Lake Preserve: With an abundance of wildlife and home to a large water-filled kettle hole formed more than 10,000 years ago, Laurel Lake offers 14 miles of hiking trails in the Town of Southold.

Shelter Island

To experience scenic beauty surrounded by historical significance, Shelter Island has 20+ properties to explore from gorgeous nature preserves to well-marked trails for the avid hiker. Since 1998, the Town has preserved 363 acres of land with fisheries, viewsheds, endangered plants, and animal species.

Mashomack Preserve

  • Mashomack Preserve: Edged in by 11 miles of coastline, Mashomack on Shelter Island is considered one of the richest habitats in the Northeast covering 2,350 acre of interlacing tidal creeks, mature oak woodlands, fields, freshwater marshes, and underwater lands to explore and enjoy.
  • Turkems Rest Preserve: For peace and quiet, Turkems Rest has a single trail that leads to Shelter Island’s largest body of fresh water. The incomparable view is accompanied by the osprey birds that nest in the trees and the gorgeous fall colors that surround the pond.
  • Sachem’s Woods: Accessible through North Midway Road or Route 114, Sachem’s Woods is located on 36 acres of land with a looping trail a little over a mile that winds through an enchanting forest of oak and beech with a large white pine in the majestic center clearing.
  • Bunker City County Park: One of the few places on Shelter Island where you can see beyond the Forks into the Atlantic, Bunker City is best accessible through Menhaden Lane off Gardiners Bay Drive. A coastal preserve, the 35-acre tract of land is home to protected species such as Eastern Prickly Pear Cactus and Red Cedar.

South Shore

While the South Shore of Long Island is most popular for its white-sand beaches in the summer, there are so many go-to places to experience the beauty of fall from state parks to arboretums with well-preserved nature trails and miles of hiking.

Credit: Bridgette Kistenger/Connetquot River State Park

  • Connetquot River State Park: With over 50 miles of hiking, horseback riding, nature trails, and fishing on the Connetquot River, this state park and preserve has over 3,000 acres of land and water for the protection of its animals. Pop in for a hike and leave with some selfies with your new furry friends.
  • Bayard Cutting Arboretum: Located in Oakdale, the arboretum has 690 acres of lawns and open meadows, a wildflower garden, a marshy refuge, and many nature trails for bird watching. Serving as an oasis of beauty and quiet, the arboretum is a source of pleasure, rest, and refreshment.
  • Prosser Pines Preserve: As Long Island’s only true forest, the preserve is one of the most impressive places to catch the changing of the leaves. Offering 15-acres of white pine forest views, this park serves as the ideal backdrop for any fall photography.
  • Cedar Creek Park: This park in Seaford is a great place to be active while taking in the views. With paths available for walkers, runners, AND bikers, this 259-acre park also serves as the entry point for a six-mile paved path to Jones Beach.

South Fork

The celebrity famed Hamptons on Long Island’s South Fork is known for the glitz, glam, and luxury that summer has to offer. But did you know that the South Fork also has gorgeous fall foliage to catch on a hike or while on a biking excursion?

Credit: @alexiscorrykapel/Instagram

  • Red Creek Town Park: Located on Old Riverhead Road in Hampton Bays, the park has a well-marked nature trail that winds over hills and pine barrens. Choose between the 3.3 mile or 1.6-mile hike to get the full fall experience in the Hamptons.
  • Northwest Woods: For those looking for good South Fork hiking AND biking trails, try out the mostly single-track loop for intermediate hikers and bikers in the Northwest Woods. With trails leading to the bay, bikers can breeze by and admire all the splendor fall has to offer.
  • Sears Bellows County Park: A hidden gem of Long Island, the 979-acre Hampton Bays park offers an extensive trail system to attract hikers and horseback riders with a beautiful forest that leads down to the water.
  • Westhampton Dwarf Pine Plains: Known for its rare dwarf pine trees, this preserve is one of three dwarf pine forests in the world. The trail is shorter than most on this list but the trek through the unique and rare ecosystem makes it worth it.

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