Our Favorite Family-Friendly Fall Activities in Montauk & Newport

By Editor 2021, November

We might be biased, but we think Newport and Montauk are perfect places to explore with family members of all ages. Need some convincing? Below, we’ve highlighted some of our favorite fall activities to help you and your family experience the peak seasonal splendor of our seaside homes.


Autumn Adventures: Apple Picking, Wagon Rides, Pumpkins, and more

When it comes to scenic fall activities, Hank’s PumpkinTown wins best in show. Located in Water Mill, this ambitious farm has it all: corn mazes plural (they have three), apple picking, wagon rides, cider donuts, and of course, a pumpkin patch. If you’re hoping to hop around, other local options include Bridgehampton’s Fairview Farm (think corn maze, pumpkins, and a corn cannon) or Water Mill’s The Milk Pail (another longtime staple for pumpkins, apple picking, and wagon rides).

Get Involved: 40th Annual Montauk Fall Fest

This autumnal Chamber of Commerce event is back (October 9th and 10th) on the Village Green with live music, pumpkin painting, and crafts for kids. The annual Clam Chowder Contest returns, too, where 20 local restaurants compete for the coveted title — not to brag, but our very own Showfish will compete this year, and our chowder has the chops! As soon as you arrive, pick up a commemorative mug to try either red or white clam chowder from some of your favorite spots, and don’t forget to vote for your favorite batch.

Halloween at Gurney’s Montauk Resort 

Halloween is right around the corner and we're celebrating with our signature Halloween Hideaway on Saturday, October 30th. Check out our special candle-making station in the Great Hall for kids of all ages, plus palm and tarot card readings in the evening for adults. Families can enjoy our special scavenger hunt, trick-or-treating, and Halloween-themed activities around the resort all weekend long.



Fall Fun: Hayrides, Corn Mazes, Pumpkins, and more

This is New England, after all, which makes Rhode Island the perfect spot for quintessential fall activities. Start with a classic hayride at Pachet Brook Tree Farm (and, while you’re there, buy a pumpkin to bring home for Halloween. For some family bonding, get lost in the eight-acre corn maze at Escobar’s Highland Farm, and tour their dairy farm on a festive hayride (wave to the cows when you roll by). Looking for even more pumpkins? Stop by Sweet Berry Farm in Middletown where you can pick your own pumpkin straight from their patch. And, if apple picking is on the autumn agenda, stop by Rocky Brook Orchard (, also in Middletown, where over 80 varieties of apples are up for grabs.


Be Adventurous on Goat Island: Newport Sailing School

Sure, you’re on vacation, but a sailing class is something even the kids will get behind. Offered on the water or in a dockside classroom overlooking the marina, it’s available for all ages every day of the week. But if you’d prefer to take it easy, you’re in luck: the school also offers tours of the harbor and Narragansett Bay.