Halloween & Pumpkin Festivals Near Boston 2026
Fall is a magical time in Mass and New England and there is a ton going on. I separated out pumpkin patches over here if that’s more your thing. This is focused on the festivals, parades, jack-o'-lantern walks and trick-or-treat events that only happen on specific dates in October, so its time to plan ahead.
Updated in September 2026 — every date below was checked against the organizer's own site. The annual events that hadn't posted 2026 dates yet are at the bottom, with what they looked like last year. October things sell out and get rained on - double check weather and alternate dates before you drive out.
Quick answers
When do Halloween events start around Boston?
October 1. Salem's Grand Parade opens Haunted Happenings that Thursday night, and the jack-o'-lantern walks at Stone Zoo, Providence and Long Hill all light up the same week. The free city events cluster mid-to-late month — Fall-o-Ween on the Common is Friday, Oct 16 and PruBoo is Sunday, Oct 25 — and Halloween itself is a Saturday this year, so neighborhood trick-or-treating is Oct 31. Farm stuff (pumpkins, mazes, hayrides) is already running now.
Which are best for toddlers?
Daytime, short, and free: PruBoo (indoor, stroller-friendly, done by 1pm), the Howl-o-ween Pet Parade in Salem (costumed dogs at 10:30am, over before nap), Somerville's Truck O' Treat (one hour on a weeknight), and Krochmal Farms on a weekend morning. Of the night walks, Long Hill is built to dazzle rather than scare and under-2s are free, but it's a walk in the woods after dark — carrier, not stroller.
Is Salem worth it with kids?
Yes, on a weekday or in the first two weeks of October. No, on the last two weekends. Halloween falls on a Saturday in 2026, so the city will hit capacity early that week and parking is a lost cause. Take the commuter rail from North Station (about 30 minutes) and go for one specific kids' event, not "Salem in general."
The October calendar at a glance
Thu Oct 1 — Haunted Happenings Grand Parade, Salem (free)
Oct 1–30, Wed–Sun nights (plus Tue Oct 27) — Halloween on the Hill, Long Hill, Beverly
Oct 1–31, Thu–Sun nights — Jack-O'-Lantern Nights, Stone Zoo
Oct 1–Nov 1, nightly — Jack-O-Lantern Spectacular, Providence
Oct 2–12 — Topsfield Fair
Weekends through Oct 25 — Krochmal Farms Pumpkin Festival, Tewksbury (free)
Sat Oct 10 — Howl-o-ween Pet Parade, Salem (free)
Fri Oct 16 — Fall-o-Ween Children's Festival, Boston Common (free)
Sat Oct 17 — Keene Pumpkin Festival, NH (free); Kids' Fun Fest, Salem Common (free)
Oct 17–18 & 24–25 — AppleFest, Wachusett Mountain
Sun Oct 25 — PruBoo trick-or-treat, Prudential Center (free)
Sat Oct 31 — Beacon Hill trick-or-treating (free)
Through Nov 1 — The Great Jack O'Lantern Journey, Southwick's Zoo
2026 dates not announced yet — Jamaica Pond Lantern Parade (usually the third weekend) and Somerville's Truck O' Treat (usually the second-to-last Thursday); both below
Free, and in the city
Fall-o-Ween Children's Festival — Boston Common Frog Pond
📍 Boston Common | 👶 All ages | 💲 Free | ☀️ Outdoor
Friday, October 16, 5–8pm. Kids go through a "haunted zombie maze" that is not actually scary, ride a trackless train, take the scarecrow slide, do crafts, and eat whatever the dairy truck is handing out. Costumes on. It's the Frog Pond, so you can take the T and leave the minute someone melts down.
PruBoo — Prudential Center
📍 Back Bay | 👶 Best under 8 | 💲 Free ($5 bag donation optional) | 🏠 Indoor
Sunday, October 25, 11am–1pm. Trick-or-treat at 30+ stores and restaurants inside the Pru, plus face painting, a magic show, crafts and live music. No registration. It's indoors, which makes it the rain plan for the last weekend before Halloween. Bring your own bag or give $5 for one — that money goes to Boston Children's Hospital.
Salem for littles — Grand Parade, Howl-o-ween Pet Parade, Kids' Fun Fest
📍 Salem | 👶 All ages | 💲 Free | ☀️ Outdoor
Grand Parade: Thursday, October 1, 6:30pm, Shetland Park to Salem Common, done around 8. This is opening night for the whole Salem October — floats, marching bands, every kid in costume. This year's theme is "Old-School Halloween." Get there early for a curb spot; it's a school night and runs late for the little ones.
Two more kid-scale Saturdays inside the month-long circus, both confirmed for 2026: the Howl-o-ween Pet Parade on Saturday, October 10 (10:30am at Derby Wharf — hundreds of dogs in costume, free to watch, $5–10 to enter your own, over before nap) and Kids' Fun Fest on Salem Common on Saturday, October 17 (from 10am — games, crafts and entertainment; hauntedhappenings.org lists any extra Saturdays). Honest warning: Halloween is a Saturday this year, so Oct 24–31 is a crowd you don't want with a stroller. Commuter rail from North Station, not the car.
Free neighborhood Halloween
The three that feel like the actual holiday rather than an event. Two of them hadn't posted 2026 dates when I checked, so here's the pattern to plan around.
Jamaica Pond Lantern Parade
📍 Jamaica Plain | 👶 All ages | 💲 Free; lanterns $5–10 | ☀️ Outdoor, dusk
2026 not announced as of September. Last year: Sat–Sun, October 18–19, 5:30–8:30pm — it's always the third weekend of October, so pencil in Oct 17–18 and watch Spontaneous Celebrations for the confirmation. Kids carry a paper lantern around the pond at dusk with a few thousand other families, most of them in costume — one of the best-looking things Boston does all year. Buy a lantern ahead at City Feed, grab a $5 DIY kit, or make one at the workshops the week before. The loop is 1.5 miles on a flat path, wagon-friendly. Sunday is calmer than Saturday. Orange Line to Green Street and walk.
Truck O' Treat — Somerville City Hall
📍 Somerville | 👶 Toddler–elementary | 💲 Free | ☀️ Outdoor
2026 not announced as of September. Last year: Thursday, October 23, 5–7pm, rain date Oct 30 — the city posts it about two weeks out, and it has landed on the second-to-last Thursday of October each year. Kids trick-or-treat along the City Hall concourse, climb around a decorated city truck, and play lawn games. It's short, it's early, and it's the ideal costume dress rehearsal for a two-year-old who isn't sure about the whole idea. Highland Ave, an easy walk from Davis or the 88/90 bus.
🔗 somervillema.gov (last year's announcement)
Beacon Hill trick-or-treating — Halloween night
📍 Beacon Hill | 👶 Ages 3+ (leave the stroller) | 💲 Free | ☀️ Outdoor
Saturday, October 31. Last year the city closed the streets between Charles and Joy (Pinckney, West Cedar, Myrtle, South Russell) from roughly 4 to 7:30pm and thousands of kids worked the brownstones; Louisburg Square is the showpiece and gets shoulder-to-shoulder. With a Saturday Halloween this year, expect the biggest crowd yet. Go 4–5:30 with little ones, bring glow sticks for the dark side streets, and take the Red Line to Charles/MGH — there is no parking. If your kid hates crowds, this is the one to skip in favor of your own block.
Jack-o'-lantern walks
If what you typed into Google was "pumpkin festival near Boston," this section is probably what you meant. These are evening walks through thousands of carved pumpkins. They are beautiful, they run late, and they sell out on weekends.
Jack-O'-Lantern Nights — Stone Zoo
📍 Stoneham | 👶 All ages | 💲 From about $16; under 2 free; separate from daytime zoo admission | ☀️ Outdoor, evenings
October 1–31, Thursday–Sunday, 5:30–9:30pm, last entry 8:30. Hundreds of lit pumpkins, pumpkin sculptures up to 18 feet tall, carved giraffes and rhinos and bison, and a giant pumpkin chair for the photo. Twenty minutes from the city — the closest big display to Boston by a wide margin, and the one to pick if bedtime is a real constraint.
Halloween on the Hill — Long Hill, Beverly
📍 Beverly | 👶 All ages; under 2 free | 💲 $32 adult / $15 kids 3–15 ($27 / $10 for Trustees members); Wed–Thu value nights $25 adult | ☀️ Outdoor, evenings
October 1–30, Wednesday–Sunday, 5:30–8 or 8:30pm depending on the night, plus Tuesday, October 27; closed Wednesday, October 7. Confirmed for 2026. The Trustees line a woodland trail with hand-carved jack-o'-lanterns and oversized Halloween sets — a graveyard, a pirate ship — silly more than spooky, which makes it the night walk to start with for kids under five. Cider-and-donut tent halfway. Advance timed tickets only, nothing sold at the gate, and October weekends sell out, so book now. Wednesday and Thursday value nights are cheaper and noticeably emptier. About 40 minutes from Boston, and it's apple-picking territory — do the orchard in the afternoon and the trail at dusk.
Jack-O-Lantern Spectacular — Roger Williams Park Zoo
📍 Providence, RI | 👶 All ages | 💲 Mon–Thu $20 adult / $16 child (2–12); Fri–Sun $23 / $19; under 2 free | ☀️ Outdoor, evenings
October 1 – November 1, nightly 6–10:30pm. The original, and still the biggest — thousands of carved pumpkins along a trail through the zoo, many of them themed scenes that are actual art. Tickets are timed, online only, and must be bought in advance; weekends go. It's an hour from Boston, so go on a weeknight: cheaper, shorter lines, and you're still home by 9. Kids will be up late. That's the deal you're making.
The Great Jack O'Lantern Journey — Southwick's Zoo
📍 Mendon | 👶 All ages | 💲 About $21 adult / $13 child (3–12) online, more at the door; under 2 free | ☀️ Outdoor, evenings
September 25 – November 1. Thousands of pumpkins plus performers — acrobats, jugglers, the "Witches of Southwick." It's a separate ticket from zoo admission and about 50 minutes west. Their site wasn't loading when I checked the dates, so confirm the nights before you buy.
Hollowed Harvest: Wicked Labyrinth — Salem
📍 Salem, 300 Derby St | 👶 All ages, mildly spooky | 💲 General admission $17–20 | 🏠 Indoor
Salem's indoor pumpkin labyrinth: hundreds of carved jack-o'-lanterns in dark corridors, a spider-web tunnel, a skeleton "concert," a pumpkin funeral. Rain or shine. The 2026 dates weren't posted when I checked; last year it ran mid-September through Halloween. The dark corridors are fine for most kids and a lot for some four-year-olds.
Farm festivals and fairs
Krochmal Farms Pumpkin Festival — Tewksbury
📍 Tewksbury | 👶 Best 2–10 | 💲 Free entry and parking; $7 hayride, $7 pony ride, $7 corn maze, $2 to feed the animals | ☀️ Outdoor
Weekends September 19 – October 25, plus Columbus Day (Oct 12), 10am–5pm. Hayride, pony rides, corn maze, goats and sheep to pet, pumpkins to pick. On the October dates the hayride becomes a "Safe Trick or Treat" — costumed characters along the route hand out candy. Thirty-five minutes up 93, no ticket, and you only pay for what your kid actually wants to do. This is the straightest answer to "pumpkin festival near Boston."
Topsfield Fair
📍 Topsfield | 👶 All ages | 💲 $15 advance; children under 8 free with an adult ticket | ☀️ Outdoor
October 2–12. The oldest county fair in the country: the giant pumpkin weigh-off, barns full of animals, midway rides, fried everything. Buy tickets before it opens — the price goes up once it's running. A weekday afternoon is the sane version; Saturday is the parking-in-a-field version.
AppleFest — Wachusett Mountain
📍 Princeton | 👶 All ages; under 5 free | 💲 Ticketed — the 2026 price wasn't posted when I checked | ☀️ Outdoor
October 17–18 and 24–25, 10am–5pm. The skyride up the mountain at peak foliage, magic and circus shows, contests, roaming characters, apples. It's a bit over an hour west, and it's the same weekends the leaves turn out there, so it doubles as the foliage trip.
Keene Pumpkin Festival — Keene, NH
📍 Keene, NH | 👶 All ages | 💲 Free | ☀️ Outdoor
Saturday, October 17. The tower of lit pumpkins, carving stations, live music on three stages, kids' games and crafts. It's two hours, so it's a day trip, and this year the layout shifted to Railroad Square because of road work downtown — follow the signs, not last year's memory.
Not announced yet (as of September 10)
These happen every year and hadn't posted 2026 dates when I checked. Here's what they were last year so you know what to watch for.
Halloween Spooktacular — Boston Children's Museum. After-hours trick-or-treat through the whole museum, pumpkin putt-putt, zombie bowling, a creepy-crawly animal show. Last year: a Saturday in late October, 5–8pm, $30 a person, sold out. bostonchildrensmuseum.org
Zoo Howl (Franklin Park Zoo) and Boo at the Zoo (Stone Zoo). Daytime trick-or-treat among the animals, usually the last weekend of October, included with admission. zoonewengland.org
Tales of the Night — Drumlin Farm, Lincoln. Candlelit paths, nocturnal animals up close, a nursery-rhyme trail for the littles, a haunted hayride for the bigger ones. Usually two nights in late October; registration required and it fills. massaudubon.org
Neponset Pumpkin Parade — Pope John Paul II Park, Dorchester. Free. Bring a carved pumpkin and a costume; they light the pumpkins, there's candy and hot chocolate. Last year: a Thursday in late October, 5:30–7:30pm. neponset.org
Davis Mega Maze — Sterling. The big corn maze plus farm festival, weekends late September through Halloween. Last year about $27–30 at the gate. davismegamaze.com
Making it work with kids
Jack-o'-lantern walks are a bedtime problem. They don't start until dark. Under-fours do better at Krochmal or Fall-o-Ween; save Providence for the year they can stay up.
Weeknights for the ticketed ones. Cheaper at Providence, shorter lines everywhere, and you'll actually get a parking spot.
Two things a weekend, not three. A farm in the morning and a pumpkin walk at night is a full day. Adding a fair to that is how everyone ends up crying in the car.
Bring a flashlight and a real jacket. October nights near Boston are 45 degrees by 8pm, and the paths are dark on purpose.
For the actual picking, Pumpkin Patches Near Boston has the farms and opening dates, and Apple Picking Near Boston covers the orchards. The year-round list is 150+ Things to Do with Kids in the Boston Area.
And for what's on each week, subscribe to Boston Family Calendar. Every Wednesday, free.
see you out there fellow parents,
Dito from Boston Family Calendar
