The air is crisp, homemade pies are bubbling and pumpkin spice lattes are in high demand. What better way to take in the splendor of the fall season than with a selection of scenic road trips through this iconic East Coast destination. With a coastline that spans over 120-miles in length and charming downtowns perfect for exploring, it’s no secret that Long Island is ideal for scenic road trips year-round but there is something special about the changing leave colors that make a fall road trip an essential experience.

Whether you are on the hunt for the perfect fall foliage, an over-the-top back-to-school shopping experience or the perfect u-pick day on the farm, the following road trips will have you in a seasonal state of mind in no time.

Follow The Foliage

Dubbed by USA Today as one of the most incredible destinations to visit in the fall, Long Island’s foliage factor is impressive to say the least, but why not add a twist of history to your trip this year. Take a drive through the region’s storied Gatsby-esque Gold Coast, once home to society’s who’s who and now these grand estates and gardens are open to visitors who wish to relive history. Start your trip at Sands Point Preserve, the famed “East Egg” of F. Scott Fitzgerald’s The Great Gatsby. Gardens and trails are open Wednesdays through Saturdays from 11 a.m. – 6 p.m. and Sundays 9 a.m. – 6 p.m. Drive through the tree-lined roads of the North Shore to Old Westbury Garden’s featuring 200-acres of formal gardens. Pre-purchase tickets for visitation 11 a.m. – 6 p.m. on Mondays, Wednesdays, Thursdays, and Fridays. End your road trip in Oyster Bay at Planting Fields Arboretum and explore 400-acres of gardens designed by the Olmsted Brothers, known for the gardens at New York’s Central Park, open daily from 9 a.m. – 5 p.m.

An Elevated Shopping Experience

Renowned for its buzzing summertime vibes, The Hamptons is also a picturesque fall escape, where chic inns transition from beachside escapes to cozy hideaways, and fewer crowds make fall shopping excursions luxurious outings. Take a drive down Montauk Highway and stop at some of the 13 hamlets that officially make up The Hamptons region lining Long Island’s South Fork. Start in Southampton and pop into the many chic storefronts that line its Main Street, around the corner the Southampton Arts Center boasts an array of art installations the perfect complement to any shopping experience. Drive on to Watermill and brush up on your art history with a visit to the Parrish Art Museum, where artworks ranging from Alec Baldwin to Roy Lichtenstein line the walls. Stop at The Milk Pail to pick up some farm-fresh goodies at their market or grab a bag and pick-your-own selection of apples and pumpkins- it is fall after all. End in East Hampton, the original Hamptons hamlet, for the ultimate shopping experience. Pop into some of the many boutiques that line Main Street and if you want to extend your visit stay overnight at The Baker House 1650, an award-winning B&B complete with a luxurious spa and lap pool – the perfect way to end your fall shopping retreat.

Harvest Check List

With over 30,000 acres of active farmland on Long Island, a Fall road trip itinerary wouldn’t be complete without a visit to a few of our seasonal favorites. Start at the Suffolk County Farm and Education Center in Yaphank, the perfect all-in-one fall spot if you are looking to avoid traveling further East. Pick pumpkins, feed the animals, or take a wagon ride through their sunflower field for the ultimate Instagram-worthy shot, either way, this centrally located, family-friendly farm is perfect for fall adventuring. Continue east to our iconic North Fork, home to over 60 vineyards and generations of family-owned farms including some note-worthy names you may recognize like the largest baked good brand in the United States, Entenmann’s Family Farm. Stop at Harbes Family Farm and Barnyard Adventure in Mattituck, a harvest season extravaganza complete with apple and pumpkin u-pick options, and tons of outdoor adventures for the kids with everything from corn mazes to farm animals, plus fresh flowers, gourmet treats, and farm stand favorites. Be sure to make a stop at Love Lane in Mattituck for either a quick bite at Love Lane Kitchen or to stock up on some local favorites at boutique shops including The Village Cheese Shop, Sweet Shoppe, or Lombardi’s Market. End your day at Greenport Harbor Brewery in Peconic and toast a seasonal lager as your grand finale.

If you are looking for more ideas, check out our Off-The-Beaten Path Harvest Adventures or see these Multi-day Trip Ideas!


Be sure to tag #discoverlongisland so we can follow along. Happy adventuring!