Westfield Family-Friendly Fall Activities 2026

32 family-friendly fall activities in Westfield and nearby.

With 18 family-friendly Halloween events in and around Westfield, you'll find plenty of ways to celebrate the season. Consider the big draws like Westfield's PumpkinFest for a local celebration, or perhaps a scenic drive to events in neighboring towns. Whether you're seeking a specific kind of autumn activity or just want to see what's happening, this guide highlights the local happenings.

All Family-Friendly Fall Activities Around Westfield

Westfield PumpkinFest 2026

Westfield

Family festival featuring free pumpkin carving, games, and trunk-or-treat.

Illustration of two small ghosts and a witch with a black cat carrying pumpkin buckets on a street of cozy houses at dusk (Mall-O-Ween at Holyoke Mall)

Mall-O-Ween at Holyoke Mall

Holyoke 6 mi Free

Free trick-or-treating at participating mall businesses plus a costume contest.

Illustration of two tiny costumed figures near a flag among tall golden cornstalks, with small farm houses and pumpkins (Foster Family Farm Fall Fun)

Foster Family Farm Fall Fun

South Windsor 24 mi $$

Explore three corn mazes featuring twelve national park checkpoints and prizes.

Illustration of clay kid characters, paper bats, cotton ghosts and pumpkins on a craft table with paint pots and bunting (Spooky Safari at The Zoo in Forest Park)

Spooky Safari at The Zoo in Forest Park

Springfield 10 mi

Family-friendly Halloween event with animal encounters and a trick-or-treat trail.

Illustration of clay skeleton figures in folk outfits by an altar with lit candles, orange marigolds and paper banners (Día de Muertos Community Celebration)

Día de Muertos Community Celebration

Hartford 24 mi Free

Day of the Dead celebration with mariachi, Mexican folk dance, and ofrendas.

Holyoke Mall Fall-A-Palooza

Holyoke 6 mi

Features a Gothic Teen character visit, crafts, and a dance party.

Scarecrows Along Main

Old Wethersfield 29 mi

Over 100 handmade scarecrows displayed along Main Street.

Illustration of two costumed trick or treaters with candy buckets on a dusk street of glowing houses and carved pumpkins (West Hartford Halloween Stroll)

West Hartford Halloween Stroll

West Hartford 25 mi

Trick-or-treating, music, and giveaways for costumed children across town center.

Spooktacular

Hartford 25 mi

Building-wide trick-or-treat trail, character meet-and-greets, and Halloween crafts.

Illustration of small costumed children and a witch on a sunny autumn lawn with pumpkins, hay bales and orange trees (Night In the Museum Youth Overnight Program)

Night In the Museum Youth Overnight Program

Sturbridge 33 mi $$$

Candlelit 1830s youth overnight adventures and mystery quests at the village.

Illustration of a Halloween craft scene with clay kids, a friendly ghost, bats and glowing pumpkins under party bunting (Klingberg Family Centers Trunk or Treat)

Klingberg Family Centers Trunk or Treat

New Britain 33 mi

Free reflective tote bag for the first 250 children.

Manchester Fall Festival

Manchester 27 mi Free

Features live music, local crafts, and food treats for all ages.

Illustration of a miniature carnival at dusk with a glowing ferris wheel, a small carousel, game booths and jack-o'-lanterns (Mountain Mist Halloween Harvest)

Mountain Mist Halloween Harvest

Meriden 43 mi $

Family Halloween fun featuring trunk or treat, llama petting, and carnival games.

Illustration of a corn maze path with tall golden cornstalks, small costumed figures, a flag, pumpkins and a red barn (Lyman Orchards Pick Your Own Pumpkins)

Lyman Orchards Pick Your Own Pumpkins

Middlefield 44 mi

Pick sugar and carving pumpkins overlooking the Connecticut River Valley.

Illustration of a small figure walking a path between tall golden cornstalks toward a red flag, with pumpkins nearby (Fort Hill Farms Star-Spangled Corn Maze)

Fort Hill Farms Star-Spangled Corn Maze

Thompson 48 mi $$

A Betsy Ross flag maze celebrating 250 years of American history.

Illustration of clay figures in costumes mingling among striped market tents and pumpkin displays under orange autumn trees (Seymour Pumpkin Festival)

Seymour Pumpkin Festival

Seymour 53 mi Free

60th annual community festival with over 150 craft vendors

Great Pumpkin Festival

Putnam 45 mi

Unique scarecrow creations decorate the streets of Putnam.

Boo in the Woo Fall Festival

Worcester 49 mi $$

Family-friendly fall festival with live entertainment and games.

Illustration of clay figures walking past striped market stalls and pumpkins on a paved square with orange autumn trees (Corn Maze & Cider Donut Harvest Music Festival)

Corn Maze & Cider Donut Harvest Music Festival

Middlefield 43 mi $$

Pizza-themed corn maze with local CT pizza facts

Illustration of a pumpkin patch full of orange pumpkins on curling vines, with small figures, a wheelbarrow and a farm stand (Kosinski Farms Pumpkin Patch)

Kosinski Farms Pumpkin Patch

Westfield $

Family-operated farm with pick-your-own produce and homemade goods

Illustration of a red tractor pulling a wooden wagon of small costumed figures past pumpkins and autumn trees near a red barn (Fletcher Farm Pumpkin Patch & Hayride)

Fletcher Farm Pumpkin Patch & Hayride

Southampton 8 mi $

Massachusetts' #1 rated pumpkin patch and family dairy farm

Illustration of a giant grinning jack-o'-lantern float and costumed marchers parading along a tree-lined park path at dusk (Florence Rag Shag Parade)

Florence Rag Shag Parade

Florence 15 mi $

Oldest continuously running Rag Shag parade

Echo Hill Orchards Fall Events

Monson 21 mi $$

Winery bar beverages allowed in the orchard

Farmer's Hayrides

Broad Brook 21 mi $$

Hayrides, pumpkin picking, and sunflower maze on a dairy farm

Trick-or-Treat at the Museum

Holyoke 9 mi $

Museum exhibits transformed into trick-or-treat stations

Illustration of a pumpkin patch with many orange pumpkins on curling vines, a red wheelbarrow, and a small wooden farm stand (Riiska Brook Orchard Pick-Your-Own Pumpkins)

Riiska Brook Orchard Pick-Your-Own Pumpkins

Springfield 8 mi $

Pick-your-own pumpkins directly from the orchard

Naumkeag Pumpkin Show

Stockbridge 31 mi $$

Over 1,500 illuminated jack-o'-lanterns on historic estate grounds

Illustration of two tiny figures on a gravel path among golden cornstalks and pumpkins, with a red flag at sunset (Fair Weather Growers Fall Festival & Corn Maze)

Fair Weather Growers Fall Festival & Corn Maze

Cromwell 34 mi $$

16-acre farm transformed for fall fun

Illustration of a pumpkin patch with many orange pumpkins, curling vines, a wheelbarrow and a small farm stand at dusk (St. Peter's Community Pumpkin Patch)

St. Peter's Community Pumpkin Patch

Cheshire 44 mi $

Cheshire's beloved "Pumpkin Church" community tradition

March Farm Fall Festival

Bethlehem 41 mi $$

Pick-your-own apples and pumpkins with a 5-acre corn maze

Boomer's Boo Bash

Hamden 49 mi Free

Annual community Halloween celebration at Quinnipiac University

Illustration of an orange tractor pulling a wooden hay wagon with costumed characters past pumpkins, trees and a red barn (Happy Hauntings Weekend)

Happy Hauntings Weekend

Bozrah 50 mi $$

Weekend of Halloween activities including trick-or-treating and contests.

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Illustration of a Halloween gathering at dusk with a smiling ghost, costumed figures, glowing jack-o'-lanterns and lights

Food, Drink, and Parties

1 of 6 Hartford Halloween Bar Crawl Hartford

Explore 15+ downtown bars with drink specials and a costume contest

See all 6 parties & tastings →

Illustration of a small cottage with glowing windows, ghosts, jack o'lanterns and black cats under a full moon at dusk

Haunted Experiences

1 of 26 Spooky Season at Sonny's: Haunted Mini Golf & Trunk or Treat Somers

Haunted Mini Golf with live scare actors

See all 26 haunted attractions →

Illustration of a pumpkin character and a ghost performing on a lit stage with red curtains before a crowd at night

Movies, Theater, and Entertainment

1 of 5 Rope at Hartford Stage Hartford

American premiere of Morgan Lloyd Malcolm's reimagining of the gothic tale.

See all 5 shows & screenings →

Illustration of friendly ghosts on small town rooftops with pumpkins and glowing windows as two witches fly past a full moon

Unique & Unusual

1 of 9 Spirits of Christmas Past Ghost Tours West Springfield

Self-led ghost tour exploring the sinister legends behind modern Christmas traditions.

See all 9 unique events →

Find Family-Friendly Halloween Fun on Our Map!

See all trunk-or-treats, pumpkin patches, and kid-friendly events nearby.

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Westfield Halloween events map - Click to view interactive map

Frequently Asked Questions

How should we dress kids for October weather swings in Westfield?

Layer like an onion: t-shirt, zip hoodie, and a packable shell beats one heavy coat, because farm mornings can be chilly while afternoons hit t-shirt warm. Sunscreen still matters at daytime patches, hats work for both sun and cold, and gloves live in the bag after mid-October evenings. Dress costumes over base layers so warmth doesn't ruin the look.

Are there sensory-friendly Halloween options for kids in Westfield?

Increasingly yes: look for daytime sensory hours with no strobes, sirens, or costumed characters approaching kids, often on weekend mornings at farms, museums, and trunk-or-treats. Practical fallbacks work too: arrive at opening when crowds and noise are lowest, bring ear defenders, preview the event with photos the night before, and agree on a quiet-spot signal. Call ahead; many venues accommodate if asked.

How long should we plan for a family farm visit near Westfield?

Two to three hours covers the core loop, animals, maze, hayride, picking, snack, before under-6 stamina collapses; four hours only works with a real lunch break in the middle. Plan the exit before the meltdown, not after: leave one activity still wanted so the day ends on a high. Add 30 minutes for peak-Saturday parking and checkout lines.

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