The Ultimate North Fork Fall Guide

Okay travelers, I went all out for this one. Yes, I tried every apple cider donut on the North Fork for you all. It was tough — believe me — my taste buds thanked me, but my waistline… not so much. It was 100% worth it.

There’s something truly magical about autumn on the North Fork (aside from the apple cider donuts). The light softens, the vines and trees blaze in hues of amber and gold, and the salty air carries a new crispness. For me, fall is the season that grounds us in both tradition and change. It’s the time when locals and visitors alike wander the fields, baskets in hand, ready to pluck apples straight from the tree or haul pumpkins home for carving and baking. There’s a nod to tradition, nostalgia from our youth, and a celebration of the harvest.

I wanted to give you a good breakdown of where you can enjoy all things fall — plus a list of some great wellness experiences to balance out all the pumpkin beer, cider, and goodies galore. I believe in enjoying life to the fullest; everything in moderation is key. So, take what you will from this little love note to a North Fork fall.

The North Fork has a way of weaving nostalgia into every moment. Standing in a pumpkin patch at Krupski’s or crunching leaves underfoot at Arshamomaque trail, you’re not just celebrating harvest season, you’re connecting to the rhythm and heartbeat of this place.

At Sound View, we believe that the ultimate luxury is time spent immersed in the simple joys of the season: a warm cider when you check in, a walk by the water, a sack of apples heavy in hand (for the pie you’ll make when you head home). This fall, let the North Fork show you why its traditions endure.

If you’re staying with us at Sound View Greenport, you’re in the heart of harvest country. Here’s your ultimate North Fork fall guide to the best orchards, pumpkin patches, and seasonal stops.

Apple Picking on the North Fork

Breeze Hill Farm & Preserve (Peconic)

With 75+ acres of apple trees, this farm feels expansive and less crowded — perfect if you prefer a slower pace and broad variety. Closest to us, it’s an easy jaunt from the hotel.

Tip: Open 9 AM–5 PM, Thursday–Monday. Closed Tuesday & Wednesday. Always call to check U-pick status: (631) 876-5159

Harbes Family Orchard (Riverhead)

One of the most beloved farms, Harbes boasts over 27 apple varieties (Honeycrisp, Fuji, Crimson Crisp, Jonagold, and more). They pair their orchard with family-friendly fun — corn mazes, pony rides, and live music.

Tip: Arrive early to avoid Sound Avenue traffic. Once you pass the Mattituck Harbes, traffic clears heading east. These are my favorite cider donuts on the North Fork and you can find them at all Harbes Farms.

Open Monday–Friday 10 AM–5 PM, Weekends & Holidays 9 AM–6 PM.

Harbes Farms Jamesport (Jamesport)

Honeycrisp apples only. Open weekends and holidays. An easy stop on your way to or from Greenport.

Woodside Orchards (Jamesport & Aquebogue)

A quieter alternative to the big farms, Woodside offers U-pick apples alongside a hard cider tasting room. It’s perfect for those who like their apples both fresh and fermented.

Tip: Aquebogue tasting room open 11:30 AM–5:30 PM (Thursday–Monday). Jamesport U-pick weekends only, 9 AM–4 PM, cash only.

Wickham’s Fruit Farm (Cutchogue)

A historic bicentennial farm with U-pick apples. On Saturdays, enjoy wagon rides to their pumpkin fields. Don’t miss the cider and donuts at the farm stand, a perfect half-day or quick stop for goodies.

Tip: PYO apples 10 AM–3 PM. Retail stand open Monday–Saturday 9 AM–4 PM. Closed Sundays. No pets allowed.

Lewin Farms (Calverton)

A true U-pick pioneer, no frills here, just fields. They offer both apples and pumpkins, ideal if you want to do it all in one place. Not technically on the Fork, but a great stop on your way back to NYC or Brooklyn.

Pumpkin Picking on the North Fork

Harbes Family Farm (Mattituck & Jamesport)

Beyond apples, Harbes offers on-the-vine pumpkin picking at multiple locations. Their Mattituck patch is open daily; Jamesport weekends/holidays only. This is the heart of fall fun on the Fork, family run farm stand, Barnyard Adventure attraction, hedge maze, corn maze, hayrides, and the Harbes Vineyard Wine Barn.

Tip: Pumpkin picking available 7 days a week at the South U-Pick Patch. Farmstand & Barnyard: Monday–Friday 10 AM–6 PM; Weekends/Holidays 9 AM–6 PM. Wine Barn: 11 AM–6 PM daily. My favorite donuts and the Sauvignon Blanc (chefs kiss).

Krupski Farms (Peconic)

Pumpkins meet local legend here. In addition to fields, Krupski’s runs a haunted corn maze in October and their famous Jack-O’-Lantern barn is a photo favorite. My go-to for décor and fall photos.

Stakey’s Pumpkin Farm (Aquebogue)

A North Fork classic: 26 acres, 18 varieties, hayrides, a corn maze, flower house, and snack shack.

Tip: Weekdays 12–5 PM, Weekends 9 AM–5 PM. “Love at First Bite” open Fridays in October.

Gabrielsen’s Country Farm (Jamesport)

If you’re after specialty pumpkins and gourds, Gabrielsen’s delivers. Their fall festival includes live music, weekend activities, and plenty of charm.

Tip: Open 7 days a week, 8 AM–6 PM.

Fall Wine & Vineyard Experiences

Harvest season, baby! You can’t have a North Fork fall weekend without wine. The Fork is home to over 50 vineyards.

At Castello di Borghese, step behind the scenes into the barrel cellar. Their private barrel tasting tour is reserved exclusively for Sound View guests. This offers a rare preview of wines still maturing in oak, guided by owner Giovanni Borghese. They also offer regular tours and tastings open to all. Feel free to bring snacks or a picnic lunch.

Just down the road, Macari Vineyards continues to shine in autumn. Their Mattituck tasting room hosts guided flights and seasonal events like Come Over October, a month-long celebration featuring Cabernet Franc and special experiences. Sound View guests receive a complimentary splash of sparkling wine with any tasting.

For a more casual vibe, McCall Wines hosts Burger Nights every Thursday and Friday, 4–8 PM, on their lawn in Cutchogue. Locally raised burgers + estate wine + fall sky = the perfect trifecta.

Over in Riverhead, RG|NY offers unique harvest experiences: Help Us Harvest (Oct 1), a hands-on grape-picking event with wine and bites; and the RG|NY Wine Dinner at North Fork Table & Inn (Oct 26), a four-course pairing that’s become an annual favorite.
Meanwhile, Matchbook Distilling Co. in Greenport keeps spirits high (literally) with tasting experiences every Saturday from 1–6 PM and by appointment. Don’t miss Create Your Signature Gin or Ricks, Racks, Whisk(e)y & Thieves…a whiskey lover’s dream:

Private distillery tour
Tasting of four whiskies thieved straight from barrels
Discussion on barrel char and staves
10% off all bottles purchased that day

Sound View guests receive an exclusive discount on these experiences.

Wellness + Art Experiences at Sound View Greenport this October

Right here at Sound View, our fall lineup helps you reset, recharge, and reconnect.

Morning Yoga with New Moon Health & Wellness – Saturdays & Sundays, 8:30–9:30 AM, Gathering Room. Complimentary for hotel guests (code: fullmoon).
Monday Piano Bar Jazz Nights – 5:30–8:30 PM. Enjoy Jazz on the Half Shell with a $55 three-course prix fixe.
Wednesday Sid Gold’s Piano Karaoke – 7–10 PM, hosted by John Khoury (Oct 1, 8, 15 & 22). Sing your heart out with a martini in hand.
Reiki & Sound Healing with Lorraine Hayden – Oct 22, 6–7 PM. Deeply restorative, open to the public & guests receive a discount with code.
Breathwork Healing with Mary Cognat – Oct 23, 7–8:30 PM. Transformational guided breathwork session; open to the public & guests receive a discount with code.
Succulent Pumpkin Workshop with Imaginariums by Elissa – Oct 30, 5:30–6:45 PM, Library. Create your own “living art” pumpkin. Open to the public & guests receive a discount with code.

From sunrise yoga to jazz at dusk, from Reiki under candlelight to artful creation by the sea, Sound View Greenport offers a haven for reflection amid the harvest rush.

October Around the Fork

Life on the East End is about balance. Yes, you can do both, pair a full-bodied red or pumpkin beer with a moment of mindfulness or inspiration.

“Literature at Landcraft” (Mattituck) – Author talk & signing for The Enchanted Earth at Landcraft Garden Foundation, Oct 11. luminous-spaces.com
Custer Observatory Stargazing (Southold) – Saturdays, 8 PM–midnight. Bring cash. custerobservatory.org
East End Seaport Museum Blacksmith Demos (Greenport) – Weekends, 11 AM–5 PM, free. eastendseaport.org
North Fork Community Theatre: A Few Good Men – Oct 10–26. Tickets required. nfct.com
Greenport Express Miniature Railroad – Oct 31, 11 AM–3 PM. Family fun near the carousel. villageofgreenport.org
Oyster Fest – Greenport Harbor Brewing Co. – Oct 12, 12–6 PM. Live music, local oysters, and North Fork Art Collective pop-ups. greenportharborbrewing.com
Aldo’s After Dark Halloween Art Show – Oct 31. Celebrate Halloween with the North Fork Art Collective, espresso martinis, and moody art. Costumes encouraged! aldoscoffee.com
First and South Costume Contest – Oct 31, 4–6 PM. A village favorite — then head to Aldo’s After Dark for your nightcap.

From blacksmith fires to starlit skies, October on the Fork invites you to explore both the playful and the profound sides of fall.

A Perfect Fall Day Itinerary (Heading to Sound View Greenport)

Morning: Start at Harbes Orchard for U-pick and cider donuts & fall activities. Beat the traffice on your way.
Midday: Visit Macari or Borghese for wine and a picnic.Perfect next stop headed to Greenport. Lombardis on Love Lane is a great stop for sandwiches to-go.
Afternoon: Stop by Krupski’s or Wickham’s for photos and treats.
Evening: Arrive at Sound View for our beach bonfire and s’mores social hour (Thurs–Sun, 5–6 PM) smores & port complimentary for our guests, followed by dinner at The Halyard with a Sound-side sunset.

A Perfect Fall Day Itinerary (During Your Stay)

Morning: Complimentary breakfast (8–10 AM). Weekend yoga (8:30–9:30 AM). Cold plunge in the Sound for the brave!
Midday: Grab lunch at Bruce & Son or First and South. Explore Matchbook Distilling or Greenport Harbor Brewery. All these gems are in town or very close by.
Afternoon: Visit Kontokosta Vineyard or a local nature preserve; we love North Fork Audubon or Dam Pond Preserve. Orient State Park is also definitely worth the drive if you love a long walk on the beach.
Evening: Join our bonfire and social hour, then unwind with dinner at The Halyard.

Tips for the Season

Timing matters. Weekdays or early mornings are peaceful and beat the traffic.
Dress the part. Boots, layers, and a sense of adventure. (fields can be muddy if it previously rained)
Call ahead. Hours and harvest availability change daily. Farmers are not updating google or their website most of the time.
Bring cash. Some farms are cash-preferred.
Capture the light. October sunsets over the Sound are unforgettable, around 6:30 PM early in the month, shifting to 6 PM by Halloween. Make sure to bring the camera.