The Perfect Date Itinerary to Enjoy Fall’s Last Hurrah on Long Island

Fall isn’t over just yet. Make the most of your favorite season before the Christmas creep settles in.

Rumor has it that fall is America’s favorite season. (And not just because it marks the premiere of the new Will & Grace!) Before winter creeps into our souls, and forces us indoors, get out and take advantage of everything fall has to offer. As November comes to a close, we encourage settling into a long drive through the East End of Long Island, blasting Tom Petty and the Heartbreaker’s greatest hits, and stopping to take photos every chance you get of the changing leaves. Along the way, we have lined up some fantastic stops to enjoy all things fall, including the sights, sounds and flavors. Yes, of course, it’ll involve pumpkins and apples, but there are surprises too.

Don’t leave without trying the apple cannons.

First Stop: Hank’s Pumpkintown

This is the place to celebrate fall. There is so much to do here that it’s too much to list, but I’ll try. First off, it has a field of the largest pumpkins you’ve ever seen en masse. Perfect for your social media shares. This place is big though, so before you pick out your pumpkins, try out a corn maze—or three. It costs $14 to get into the Maze Park, and has three separate mazes, depending on what you are looking for. The 1-hour long adventure maze where you follow clues and use a scratch-off card to see if you’ve won a prize at the end will make you question whether you should have stocked up on corn dogs before entering, and will seriously challenge your sense of direction. In addition to corn mazes, you can jump like you’re a kid again on their 70 foot long blown up jump pad! And snack on something from their store, like roasted corn or caramel apples, as you turn back on your tunes and head to the next stop. But maybe the coolest part of the whole place are the apple cannons (bright red cannons that, yes, really shoot apples). They are seriously a thrill.


Don’t reach for that eggnog just yet; there’s still so much cider to sip!

Second Stop: Woodside Orchards

If you didn’t happen to buy a puppy, because no pets are allowed, you’ll next go to Woodside Orchards in Aquebogue. Grab a flight of their homemade hard ciders and a six pack of hot cider donuts, the lightest and fluffiest cider donuts you’ve ever had. You’re welcome to bring your own food and hang out back in a pair of adirondack chairs, overlooking their apple orchards. If you’re lucky, they’ll have a fire lit in the fire pit. Non-alcoholic cider is also available, and there is a charmingly rustic tasting room if the weather is less than ideal.

Open daily—except Wednesdays—from 11:30 a.m. to 5:30 p.m.

There’s no such thing as too many cider doughnuts.

Dinner: Cooperage Inn

Take the scenic Sound Avenue to the Cooperage Inn, in the hamlet of Baiting Hollow. It must be good if it’s in a hamlet! They pride themselves with using local ingredients, and are beloved—rightfully—for their fresh baked pies. And some nights you can score some live music amidst the country decor.

Open for dinner Monday through Thursday, 3:30 p.m. to 9:00 p.m., Friday & Saturday 3:30 p.m. to 9:30 p.m., Sunday 2:30 p.m. to 9:00 p.m.