Autumn Escapes: Best Long Island Weekend Getaways Close to Home

Who says you need to hop on a plane to feel worlds away? Fall on Long Island is basically a postcard come to life — golden leaves, cozy inns, and the smell of apple cider in the air. Whether you’re a local looking for a quick reset or scouting your next dream-home destination, these weekend getaways are all about charm, comfort, and that “I could get used to this” feeling.

🍂 1. North Fork — Wine, Water Views & Weekend Zen

If you haven’t done a fall weekend on the North Fork yet… what are you waiting for? Between the vineyards, farm stands, and seaside towns like Greenport and Cutchogue, it’s peak cozy season vibes. Sip local reds, stroll through pumpkin patches, and stay at a boutique B&B that smells like fresh-baked muffins. Bonus? You can tour some stunning new construction homes while you’re at it — think modern farmhouses with vineyard views.

🌊 2. The Hamptons — Off-Season, On Point

When the crowds head home, the Hamptons truly shine. Fall here is peaceful, stylish, and just a little bit magical. Picture: empty beaches, bonfires, and brunch without the waitlist. Plus, home-hunting in the off-season means you can explore new builds and luxury listings without the summer chaos. Try a weekend stay in Sag Harbor or Amagansett — where every corner feels like an Instagram story waiting to happen.

🌾 3. Oyster Bay — History Meets Small-Town Chic

Oyster Bay’s fall charm is unmatched. Tree-lined streets, waterfront views, and cozy coffee shops that make you want to linger all afternoon. Spend your Saturday exploring the historic district or hitting a local fall festival, then imagine calling this town home.

And if you’re serious about staying for good, check out two stunning new construction homes now available in Oyster Bay:

🏡 758 Connecticut View Dr, Oyster Bay, NY — a sleek new build by Pironi Homes that blends modern luxury with timeless coastal style.

🏡 762 Connecticut View Dr, Oyster Bay, NY — elegant craftsmanship, spacious design, and those dreamy water-view sunsets you can’t find anywhere else.

Both homes are minutes from the marina, parks, and all of Oyster Bay’s historic charm — the perfect blend of small-town warmth and modern living.

🌳 4. North Shore Nassau — Cozy Luxury with a View

From Roslyn to Sands Point, the North Shore knows how to do autumn. Picture grand homes surrounded by fiery foliage, waterfront walks, and candlelit dinners. Stay at a local inn or luxury hotel and soak up the Gold Coast charm.

And if you’re ready to make that Gold Coast lifestyle permanent, don’t miss:

🏡 36 Cow Neck Rd, Sands Point, NY — a breathtaking new construction estate in Port Washington’s exclusive Sands Point community. This modern masterpiece offers unmatched design, serene surroundings, and the kind of craftsmanship you only find in the area’s most sought-after homes.

Who says “close to home” can’t feel like a five-star escape?

🌻 5. Huntington — Arts, Eats & Autumn Nights

Downtown Huntington has that perfect mix of culture and comfort. Catch a live show, grab dinner at one of the town’s foodie-favorite restaurants, and browse the local boutiques. It’s a vibe — and a great way to see how new construction homes are blending modern design with small-town life.

🏡 Your Fall Getaway Might Just Become Home

The best part about living on Long Island? You don’t need to go far to feel like you’ve gone somewhere. Every weekend trip could be a sneak peek at your future neighborhood — and with new construction homes popping up across the island, your perfect “escape” might just become permanent.

🍁 Find your next home-sweet-home at mylestonehome.com — where local living meets luxury new construction.

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