Sound Views this Fall on the North Fork

Sound Views this Fall on the North Fork

There’s something about fall on the North Fork. The roads wind past farm stands piled high with apples and pumpkins, vineyard rows turn shades of gold, the air coming off the Sound gets a little crisper, and Greenport settles into one of our favorite seasons of the year. From apple picking and cider donuts to harvest weekends, maritime traditions and a television festival right here at Sound View, September and October are packed with reasons to head east. If you’re staying with us at Sound View Greenport, consider this your starting point for fall on the Fork.

Apple Picking Season Is Here

September means apple season, and the North Fork has everything from historic orchards and simple pick-your-own fields to full-fledged fall festivals. Picking schedules change throughout the season based on weather and what’s ripe, so we always recommend checking with the farm before heading out.

• Breeze Hill Farm & Preserve | Peconic: One of the closest apple-picking options to Sound View, Breeze Hill is a beautiful stop in Peconic with sprawling orchards and a quieter, old-school North Fork feel. The farm spans more than 75 acres and is a great choice if you want to make apple picking the focus of a long and slow afternoon. The farm stand is currently open Friday through Sunday from 9 AM–5 PM. Call ahead for current U-pick availability.
• Wickham’s Fruit Farm | Cutchogue: A true North Fork institution. Wickham’s is a historic bicentennial farm that has been worked by the same family for generations. Pick-your-own apples are currently offered Saturdays from 10 AM–3 PM, with wagon rides typically bringing guests out to the orchard. Stop at the farm stand afterward for fresh cider, cider donuts, pies and whatever else happens to be coming out of the kitchen that day. Wickham’s is closed Sundays.
• Harbes Farms Jamesport | Jamesport: For Honeycrisp lovers, this is your stop. Harbes Jamesport has acres dedicated to Honeycrisp apples, with weekend apple picking alongside hayrides, an America 250-themed corn maze, jump pads, live music and plenty of fall treats. It’s a particularly good choice for families looking to make an entire afternoon out of apple picking. Open Saturdays and Sundays from 9 AM–6 PM through November 1.
• Harbes Orchard | Riverhead: The biggest fall production of the bunch. Harbes Orchard offers a large pick-your-own orchard with more than two dozen apple varieties throughout the season, plus its corn maze, seasonal food and drinks, family activities and plenty of cider donuts. Apple varieties rotate as they ripen, making this a fun one to revisit throughout the season. Weekends tend to get busy, so our tip is always the same: go early.
• Woodside Orchards | Jamesport: For a more relaxed apple-picking experience, we love Woodside. Their Jamesport orchard opens for U-pick on September 17, with weekend picking from 9:30 AM–5 PM and last call for picking at 4:30 PM. Afterward, head to Woodside’s Aquebogue tasting room for a flight of their house-made hard cider and, naturally, a cider donut or two.
• Lewin Farms | Calverton: Lewin Farms is about as classic as pick-your-own gets. The furthest from us but great to stop on your way off the fork. No elaborate production necessary, just fields, orchards and whatever is ripe. Apple picking runs from late August through October, depending on crop conditions, with pumpkins and gourds joining the lineup later in September. Lewin updates availability frequently, so call before making the drive.

Our fall rule: picking conditions can change quickly. A rainy day, a busy weekend or a particularly good crop can completely change what’s available. Always check directly with the farm the morning you plan to visit.

Next Up: Pumpkin Season

Apples get September. October belongs to pumpkins. As we move into late September and October, North Fork fields fill with pumpkins, gourds, corn mazes, hayrides and plenty of opportunities to embrace peak fall. A few farms to keep on your radar:

• Krupski Farms | Peconic
  A longtime local favorite for pumpkins, gourds and fall décor, with an especially fun atmosphere as Halloween approaches.
• Harbes Family Farm | Mattituck + Jamesport
  On-the-vine pumpkin picking, corn mazes, hayrides and plenty of family activities make Harbes one of the biggest fall destinations on the North Fork. The farm has so much more to offer than just u-pick including a barnyard adventure, award winning vineyard, & farm stand.
• Gabrielsen’s Country Farm | Jamesport
  Specialty pumpkins, gourds and plenty of classic farm-stand charm make this an easy addition to a fall drive.
• Stakey’s Pumpkin Farm | Aquebogue
  A North Fork fall classic with a 26-acre U-pick pumpkin field, multiple pumpkin varieties, hayrides, a corn maze and seasonal food. Opening day for 2026 is September 19, with weekday and weekend picking continuing through October 31.
• Lewin Farms | Calverton
  Pumpkins, gourds and winter squash generally begin in mid-to-late September and continue through late October.

Stay tuned…we’ll be sharing our full North Fork Pumpkin Picking Guide as October approaches, with updated picking schedules, corn mazes, hayrides and our favorite fall farm stops.

September Highlight: The 36th Annual Greenport Maritime Festival

Fall in Greenport officially gets underway with one of the village’s most beloved traditions: the 36th Annual Greenport Maritime Festival, September 25–27, 2026. For more than 35 years, the festival has celebrated Greenport’s maritime heritage, working waterfront and the people who make this village what it is. This year brings a full weekend of food, music, boats, makers and longtime Greenport traditions throughout Mitchell Park, the marina and downtown village.

Friday, September 25 | Land & Sea Gala

The weekend begins Friday evening at 6 PM with the Land & Sea Gala, returning to downtown Greenport in Mitchell Park. Sip, snack and dance the night away with tastings from local restaurants, drinks and live entertainment, all while celebrating Greenport and its maritime history along the waterfront. General admission is $125.

Saturday, September 26 | Maritime Festival

Saturday brings the festival into the streets of Greenport with the Maritime Parade at 11 AM, followed by a full day of village-wide programming. Look for community rowing in Greenport Harbor, the Pie Eating Contest, Fishing Derby, classic boats in the Bug Light Classic Regatta, local vendors, food, live music and the weekend-long Family Treasure Hunt winding its way through Greenport landmarks and businesses.
As evening arrives, the East End Seaport Museum keeps things going with its Regatta, Reggae & Rum Party at 6 PM on the waterfront.

Sunday, September 27 | One More Day by the Sea

Sunday keeps the maritime spirit going with community rowing, the Oyster Shucking Contest at 10 AM, food and activities throughout the village, and one of the weekend’s most entertaining traditions: the Cardboard Boat Race at Mitchell Park Beach. Build it. Float it. Hope for the best.

The festival is free to explore Saturday and Sunday, with select competitions and special events requiring registration or tickets. Find the full schedule, Land & Sea Gala tickets and registration information at the Greenport Maritime Festival website.