Once the summer crowds thin out and that first cool breeze rolls off the Atlantic, Long Beach transforms. The boardwalk empties just enough to feel like yours again, the surf takes on a steelier hue, and suddenly everyone's swapping beach bags for flannels and planning their next trip "out east." If you're settling into one of Long Beach, NY's, apartments for rent, you're already in the perfect spot to experience the best of what fall has to offer on this island.
Because here's the thing most people don't realize until they live here: Long Island in the golden season is spectacular. We're talking apple orchards glowing under blue skies, vineyard rows heavy with the last grapes of the term, and forest trails carpeted in copper. Some of the best foliage around here rivals anything you'd find in New England, and it's all less than an hour from your front door. The lineup of fall activities in Long Island runs deep, and this guide covers the experiences worth building your weekends around.
Apple Picking, Corn Mazes and Cider Donuts
No fall is complete without at least one trip to a farm. It's practically a rite of passage once the agenda flips to September, and the options range from sprawling rural destinations to dirt-under-your-nails operations. For residents looking for the best apple picking in Long Island, NY, two spots deserve a permanent place on the calendar.
Hank's Pumpkintown in Water Mill is the one your coworkers won't stop talking about, and for good reason. This 420-acre harvest destination sits out in the Hamptons and features just about everything you'd want from a fall outing:
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Apple picking across multiple heritage varieties
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Massive corn mazes that genuinely challenge your sense of direction
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Pumpkin patches stretching farther than you can see
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Freshly made cider donuts that sell out for a motive
The drive is roughly 90 minutes from Long Beach, which makes it ideal for a full Saturday adventure.
A quick tip: weekday visits are significantly less hectic, so if your schedule allows a Tuesday or Wednesday trip, take it.
For something a bit more low-key, Lewin Farms in Calverton offers a wonderfully rustic alternative. As Long Island's first pick-your-own farm, it carries a no-frills authenticity that feels refreshingly honest. Fall brings bushels of crisp apples, pumpkins in every shape imaginable, and seasonal gourds perfect for decorating your apartment. Lewin sits about 75 minutes northeast of Long Beach, and since it's close to the North Fork, you can easily pair a morning of picking with an afternoon of wine tasting.
The drive itself is part of the experience. Route 25 through the North Fork is dotted with roadside farm stands selling fresh pies, local honey, and late-season sweet corn. Keep your windows down and a few extra dollars handy because you will stop.
Harvest Season in North Fork Wine Country
October on the North Fork is something special. This is crush season, when the vineyards are actively harvesting their grapes and the tasting rooms start debuting new releases. The light turns golden earlier, live music floats across the rows, and the whole region feels celebratory without the summer intensity. For couples especially, an afternoon spent exploring the vineyards of Long Island, NY, is one of the most memorable seasonal experiences the island offers.
Among the many fall festivals in Long Island that pop up during harvest period, the North Fork wine trail hosts some of the most inviting. Dozens of events feature local food vendors, barrel tastings, and outdoor concerts set against a backdrop of amber-tinged vines.
Jamesport Vineyards is a longtime favorite for good reason. The tasting room pairs award-winning wines with wood-fired pizzas, and the whole setting is wonderfully relaxed. Grab a table outside, order a flight, split a pie, and let the afternoon unfold.
For a completely different atmosphere, Kontokosta Winery offers a modern tasting room perched right on the bluffs above the Long Island Sound. The waterfront panorama is stunning, particularly in October when the surrounding foliage and the Sound's blue-gray water create a dramatic contrast. Their cool-climate whites are especially worth sampling.
The North Fork is home to over 50 wineries in Long Island, NY, most of them clustered within a manageable stretch between Jamesport and Greenport. That means you can comfortably visit two or three in a single afternoon. Between stops, the charming downtown of Mattituck and its Love Lane corridor offer farm-to-table lunch spots and local boutiques worth browsing. It's among those fall things to do in Long Island that feel effortlessly sophisticated.
Foliage Walks and Nature Drives Worth the Trip
You absolutely don’t need a weekend trip to Vermont to see gorgeous fall color. Long Island's own preserves and arboretums put on a show every October and November, and two spots in particular stand out for their beauty and accessibility.
Planting Fields Arboretum in Oyster Bay spans over 400 acres and feels like stepping onto the grounds of an English country estate. This hidden gem on Long Island features Coe Hall, a stunning Tudor Revival mansion, surrounded by landscaped gardens and towering specimen trees that ignite in shades of crimson, amber, and gold each fall. It's perfect for a reflective morning walk or a leisurely afternoon spent photographing the grounds. The drive from Long Beach takes about 50 minutes via the Meadowbrook Parkway, making it a very doable half-day outing.
Closer to home on the South Shore, Connetquot River State Park Preserve in Oakdale offers a wilder, quieter kind of beauty. The trails follow the Connetquot River through forests of oak and maple, and in peak season the canopy reflects off the water in ways that genuinely stop you mid-stride. White-tailed deer sightings are common, and birders often spot osprey circling above the river. For fun fall activities, few things beat a morning hike here followed by lunch at one of the nearby Oakdale cafés.
Your October Day-Trip Roadmap from Long Beach
Planning these outings is simple once you know the routes. For eastbound trips to the farms, the North Fork, and fall festivals in Long Island, hop on Sunrise Highway (NY-27) or the Southern State Parkway early. Weekend traffic heading east can thicken by mid-morning, so aim to be on the road by 8:30 or 9:00. For North Shore destinations like Oyster Bay, the Meadowbrook north to the Long Island Expressway is your best bet.
A few practical tips to elevate the experience:
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Bring a cooler. You'll want it for farm-fresh pies, cider, and any bottles you pick up along the wine trail.
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Dress in layers. Mornings on the island can be cool and breezy, warming considerably by midday.
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Plan your pairings. Lewin Farms and the North Fork wineries sit close enough to combine into one incredible day. Pumpkin picking farms in Nassau County can be paired with Planting Fields for a shorter North Shore loop.
There's no shortage of fall things to do in Long Island, and the best part about calling Long Beach home is how effortlessly you can access all of it. Head east for orchards and vineyards, north for foliage and history, and then circle back to the boardwalk just as the sun drops low over the ocean.
That golden-hour walk home after a full day, cooler packed and boots a little muddy, is the kind of moment that makes this town feel like more than just a summer destination. If you've been thinking about planting roots in a community where ocean living meets seasonal adventure, our Long Beach residences might just be the perfect place to start your next chapter.