This North Shore Massachusetts Estate Becomes A Glowing Halloween Wonderland With Thousands Of Pumpkins
Somewhere on the North Shore, a woodland trail glows with well over a thousand carved jack-o’-lanterns. Some years, the count creeps close to two thousand.
That’s a lot of pumpkin faces staring back at you in the dark.
The twist? This happens on the grounds of a historic estate once owned by a famous magazine editor.
Formal gardens by day turn into a lantern-lit maze of scarecrows and themed scenes by night.
I appreciate that the whole thing aims for spooky, not scary. Little kids can giggle instead of hiding behind your coat.
Hot cider and cider donuts wait halfway through, which feels like excellent planning.
Massachusetts has no shortage of fall traditions, but this one feels a little magical. So where exactly is this glowing trail, and how do you get a ticket before they vanish?
Thousands Of Glowing Faces Will Follow You Down The Trail
Long Hill, a historic estate run by The Trustees, hosts an event called Halloween on the Hill each October. The star of the show is a woodland trail lit by well over a thousand carved jack-o’-lanterns.
For the 2026 Halloween season, the estate features thousands of glowing, hand-carved jack-o’-lanterns along its woodland trail. That’s enough pumpkin light to make your porch display feel a little shy.
The walk is self-guided, so you set the pace. Stop for photos, linger at a favorite carving, or hurry past the spooky bits with a nervous giggle.
Many of the pumpkins are hand-carved with detailed designs. The event also uses durable foam pumpkins called Funkins, which hold up through the season.
That mix lets the displays stay bright and creative every single night. It also means the carvers can attempt designs that a real gourd might not survive.
The glow builds as darkness settles over the trees. Going after full dark makes the lanterns pop against the shadows.
Plan on about an hour to walk the whole trail. Comfortable shoes are a smart choice, since you’ll be on your feet the entire time.
Your eyes will be busy, so your feet deserve some comfort.
Villains, Superheroes, And Wizards Join The Pumpkin Party
Scarecrows dressed as famous Hollywood villains have greeted guests on this trail. That alone tells you the creative team has a sense of humor.
Themes change and grow from year to year. Past displays have featured jungle scenes, mythical creatures, and pumpkins inspired by Marvel superheroes.
Harry Potter fans have also spotted wizarding touches along the path in earlier seasons. Who knew a pumpkin could pull off a lightning-bolt scar?
Themed groupings are a big part of the fun. Instead of random pumpkins, you’ll find clusters that tell a little story together.
Kids love trying to name every character before their parents do. It turns the walk into a friendly guessing game that keeps everyone looking closely.
Because the themes shift, returning visitors get fresh surprises. Last year’s favorite scene might be replaced by something entirely new.
Staff and volunteers start planning these displays months ahead. That kind of early effort shows in the details, from carving style to how each scene is arranged under the lights.
Keep your camera handy. Some of these carvings deserve a spot on your phone’s lock screen, at least until November.
A Pirate Ship In The Woods Is Not Something You See Every Day
Ahoy, mateys of the forest. A haunted pirate ship has appeared among the trees during this event, and it looks wonderfully out of place.
Scenes like that turn the woodland path into a kind of outdoor stage. Pumpkins are only part of the story here.
Artistic lighting washes over the trees and decorations. Music plays along the route, adding mood without cranking up the fear factor.
Spooky music follows you through the walk, which makes every bend feel like a new chapter. It’s the soundtrack of a not-too-scary storybook.
Graveyard scenes and stylish scarecrows have also popped up along the way. Each one is built to feel playful rather than frightening.
The spooky, not scary approach matters for families with younger children. A ten-year-old and a toddler can enjoy the same walk without anyone needing a nightlight afterward.
Older kids and adults still get plenty of eerie atmosphere. Shadows, glowing faces, and creepy tunes do a lot of work in the dark.
Take your time at the bigger scenes. They reward a slower look, and you might spot small details tucked around the edges.
Cider Donuts Halfway Through Feel Like A Genius Move
Halfway through the trail sits the Concession Tent. Good luck walking past it without stopping.
Hot apple cider is on the menu, which feels perfect on a chilly New England evening. Cold apple cider is there too, for anyone who runs warm.
Then come the apple cider donuts. I can’t imagine finishing this walk without one in hand.
Boxed water and other festive sweets round out the offerings. It’s a simple setup, but it hits the season right on the nose.
Restrooms sit near the tent as well. That makes the midpoint a natural spot to regroup before the second half.
Another set of restrooms waits at check-in. Those are porta-potties, so plan accordingly with little ones.
A quick break also gives tired legs a breather. The walk takes about an hour, and small kids appreciate a snack stop more than anyone.
Bring a way to pay, since you’ll probably want a donut for the road. Sticky fingers and glowing pumpkins make a pretty classic October memory.
Grab Tickets Early Because The Gate Won’t Sell Them
Tickets are not sold on-site, so showing up hoping to wing it won’t work. You’ll need to buy them in advance.
Each ticket comes with a 15-minute arrival window. That keeps the trail from turning into a pumpkin traffic jam.
The event has run on select evenings throughout October, mostly Wednesdays through Sundays. A few extra dates have been added in past seasons, so check the schedule before you plan.
Value Nights have been offered on certain weekdays and early October dates. Those come with a different pricing tier for adults, which can help a family budget.
Long Hill sits at 572 Essex St, Beverly, MA 01915. Event parking has been located in fields off Essex Street, near the yellow farmhouse.
Arriving right at the start of your window gives you the most relaxed walk. Rushing in the dark is nobody’s idea of fun.
Dress for the weather, since the whole event happens outdoors. A warm layer or two can make the difference between cozy and shivering.
Popular nights can sell out. Booking early is the easiest way to avoid disappointed faces.
Quieter Nights Make Room For More Families
Not every kid loves loud music and crowds. Long Hill has offered sensory-friendly hours on special Friday evenings in October.
Those nights provide a calmer setting. Guests who prefer less stimulation can still enjoy the glowing pumpkins without feeling overwhelmed.
The regular trail does have challenges. Uneven ground and several sets of stairs mean it isn’t suitable for wheelchairs or strollers.
During sensory-friendly times, an alternative path has been available for guests with limited mobility. It’s a thoughtful touch that opens the magic to more people.
Parents of toddlers should keep the stroller rule in mind. A baby carrier might be your best friend on this walk.
Planning around these details makes the night smoother for everyone. Nobody wants a surprise staircase with a sleeping kid and a heavy stroller.
I appreciate events that think beyond the typical visitor. A quieter evening can mean the difference between staying home and making a new family tradition.
Check the current schedule for sensory-friendly dates before booking. They can be the sweetest way to see the lanterns at an easier pace.
A Famous Editor’s Summer Home Sets The Stage
Long before the pumpkins, Long Hill belonged to Ellery Sedgwick. He was the well-known editor of The Atlantic Monthly.
Long Hill served as the Sedgwick family’s summer retreat beginning in 1916 and remained in family ownership until 1979. Mabel Cabot Sedgwick and later Marjorie Russell Sedgwick shaped its famous gardens.
Their horticultural vision still defines the property today. The gardens have been admired for nearly a century.
The Federal Revival mansion was built in the 1920s and incorporates architectural elements salvaged from historic buildings. It includes woodwork and mantelpieces salvaged from the Isaac Ball House in Charleston, South Carolina.
That’s a pretty fancy backdrop for a pumpkin party. Somewhere, a carved jack-o’-lantern is living its best historic life.
The Trustees have cared for Long Hill since 1979. The estate covers 114 acres in Beverly, Massachusetts.
Knowing the history adds a little depth to the glowing walk. You’re strolling through grounds that a literary figure once called his summer escape.
The daytime gardens deserve their own visit too. Garden rooms, labeled plants, and woodland trails make it a lovely stop in any season.
The Greenhouse Pop-Up Shop Is Worth A Peek
Right at the start of the trail, the Greenhouse turns into a retail Pop-Up Shop. It’s an easy stop before or after your walk.
The shop carries items for both kids and adults. A small souvenir can help stretch the memory of a glowing night.
Shopping inside a greenhouse feels fitting for an estate known for its gardens. Plants by day, Halloween goodies by night.
Members of The Trustees get a discount on purchases. That’s a nice perk for folks already supporting the organization.
The Trustees care for many important natural and cultural places across Massachusetts. Membership helps fund that work, so the discount feels like a thank-you.
Kids may beg to stop on the way in. A smart strategy is promising a look at the end, once the trail is done.
Gift shoppers can also get a head start on the season. Holidays sneak up quickly after October fades.
Leave a few extra minutes in your plan for browsing. Rushing past the shop might mean missing the perfect little keepsake.
Come Back When The Gardens Steal The Spotlight
Once the pumpkins go dark, Long Hill keeps shining. Its gardens and woodland trails are open to the public year-round.
Spring brings daffodils, and rhododendrons usually put on a show around mid-May. Summer fills the garden rooms with color and unusual plant specimens.
Each garden room highlights different plants and architectural touches. Many plants carry labels, so every stroll doubles as a mini botany lesson.
Lily ponds and wooded paths add variety beyond the formal beds. Some trails wander into the forest for a quieter walk.
There’s even a small farm area with chickens and turkeys. Kids who loved the pumpkins may love meeting feathered residents just as much.
Daytime visits offer a totally different mood from Halloween on the Hill. Calm, green, and peaceful replaces glowing and spooky.
The estate makes a great North Shore outing in any season. Massachusetts weather may be fickle, but these gardens reward repeat trips.
So mark your calendar twice. Once for the jack-o’-lanterns, and once for when the flowers take their bow.