Enjoy Fall With the Whole Family With These New England Adventures

Let them ask “Are we there yet?” all the way to these family-friendly adventures—it’ll be worth it.

Taking a ride in the woods at Castle in the Clouds. / Photo by Pat Piasecki

Last updated in October 2023.


There are fairy tales, and then there’s the Castle in the Clouds, a regal Arts and Crafts château nestled in the Granite State’s Ossipee Mountains. For the best views of the verdant Moultonborough manse, take a one-hour trail ride with one of the estate’s gentle horses, which will lead you through storybook-gorgeous woods and fields with vistas of Lake Winnipesaukee. The trail ride is open only to kids eight and over, but wee ones can enjoy a guided walk to a quiet pond—or channel Cinderella with a carriage ride through the magical property.

WHILE YOU’RE THERE: All aboard the Winnipesaukee Scenic Railroad: Its restored vintage trains depart from Weirs Beach for picturesque tours through October 29.

OR TRY: Bonding with the horses at Princeton’s Cornerstone Ranch, which offers one- and two-hour guided trail rides for adults and kids 10 and over, as well as pony rides (and ice cream!) for the littlest equestrians most weekends.

A view of Topsfield Fair’s neon midway. / Photo by Apisorn Jr.


The first-place gourd at the Topsfield Fair’s 2018 Giant Pumpkin Weigh-Off clocked in at 2,114 pounds—around the size of a Chevrolet Spark. This year’s event, held September 29 to October 9, promises even more eye-popping agricultural feats—not to mention classic carnival rides and as many loaded baked potatoes and fried Oreos as you can eat.

WHILE YOU’RE THERE: Treat the fam to the “Big Papi” lobster roll for four at the Salem outpost of the South End’s Lobstah on a Roll.

OR TRY: Following the rides to Connecticut’s Glastonbury Apple Harvest & Music Festival: Held October 13–15, it features a packed music stage and, of course, a fully stocked midway.

How to Keep Your Cool on a Family Outing
Low expectations and snacks. These are the two things every parent needs before setting out on a weekend getaway with your lovable little devil. Preparation—mental and physical—can also make the difference.First and foremost, if you’re able to get into a Zen state of mind before you even leave the house, you’ll be less likely to lose it when your child inevitably does. (It’s okay to give yourself a timeout to keep from boiling over if you need to.) When it comes to what to bring, don’t be afraid to load up the diaper and cooler bags: Chances are your daughter won’t even notice the amount of anxious game-planning, not to mention the number of Ziploc bags, that went into having a good time. Wide-brim hat? You bet. Several water bottles? Of course. Enough Goldfish to feed an entire soccer team? Wouldn’t leave home without ’em. That way, whether you’re strolling through the apple fields or riding the Ferris wheel, you can be fully in the moment—and so can she.


You don’t have to wait until there’s a blanket of white on the ground to shout “mush!” At Muddy Paw Sled Dog Kennel, in Jefferson, New Hampshire, the crisp autumn months are ideal for a 2- or 5-mile snowless dogsledding tour that shows off the fiery colors of the White Mountains’ Presidential Range. The best part, though, might be the belly rubs and kisses at the beginning and end of each ride.

WHILE YOU’RE THERE: Warm your paws in front of the fire at the Glen House, a recently opened hotel with panoramic mountain-view rooms.

OR TRY: The costumed canines at Faneuil Hall’s annual Halloween Pet Parade, held this year on October 28, might not mush, but they sure look cute dressed as hot dogs, princesses, and superheroes.



Pumpkins, pig races, corn mazes, and a candy cannon. All it takes is one afternoon to knock out an entire autumn’s worth of kid-friendly fall festivities at Plympton’s Sauchuk Farm. This year’s maze was designed in the image of beloved Sesame Street characters (don’t worry if you get lost—uniformed “corn cops” are there to rescue you).

WHILE YOU’RE THERE: Early October kicks off the cranberry harvest at Stone Bridge Farm in Acushnet, where you can put on chest waders and head out into a flooded bog for a berry sweet photo op.

OR TRY: Pointing the tractor north to Connors Farm, in Danvers, for a wholesome day of apple-picking, train rides, and corn mazes.



Yes, you’ll have more than a little dirt underneath your fingernails after a day planting, weeding, and harvesting on one of the Food Project’s local farms, which aim to increase access to healthy food in Greater Boston. But that’s easy enough to wash off: What will stay with you and your teens (volunteers must be at least 14) is the experience of making our little corner of the world a better place.

WHILE YOU’RE THERE: The Food Project’s Lincoln farm isn’t far from the deCordova Sculpture Park and Museum, where you can frolic among a steel doughnut and bronze hearts.

OR TRY: Rolling up your sleeves to help green up Southwest Corridor Park, in Boston, on October 12 from 10 a.m. to noon.

Check out more New England adventures to take this fall