Family-Friendly Fall Activities Near Westport 2026

36 family-friendly fall activities near Westport

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

Halloween Nightfair

Sat, Oct 24

South Norwalk Free

South Norwalk street festival with live entertainment, vendors, and trick-or-treating.

Boo Fest by the Beach

Sat, Oct 17

Milford 15 mi

Shoreline Halloween celebration with trick-or-treating, carriage rides, and family entertainment.

Illustration of a ghost and two costumed kids trick or treating past glowing houses with pumpkins and autumn leaves at dusk (15th Annual Milford 5K Trick or Trot Run/Walk)

15th Annual Milford 5K Trick or Trot Run/Walk

Sat, Oct 31

Milford 17 mi $$$

Charity 5K run and walk featuring costume contests for Beth-El Center.

Illustration of a small clay figure on a path between tall golden cornstalks, with a red flag, pumpkins and a tiny cottage (Jones Family Farms Pumpkin Season)

Jones Family Farms Pumpkin Season

Sep 28 – Oct 31

Shelton 17 mi

Explore the farmyard, mini corn maze, walking trail, and farm animals.

Seymour Pumpkin Festival

Sun, Sep 20

Seymour 23 mi Free

60th annual community festival with over 150 craft vendors

Illustration of a giant grinning jack-o'-lantern float and costumed marchers parading along a tree-lined park path at dusk (Walnut Beach Halloween Pet Parade & Contest)

Walnut Beach Halloween Pet Parade & Contest

Sun, Oct 18

Milford 15 mi

Costumed pets walk the runway for an annual judged costume contest.

Illustration of a Halloween parade on a town street at dusk with a giant smiling pumpkin float and costumed children (Walnut Beach Halloween Parade)

Walnut Beach Halloween Parade

Sat, Oct 31

Milford 15 mi

Features a kids' costume parade and free ice cream in costume.

Illustration of tiny clay musicians playing on a hay stage among pumpkins, bunting and striped booths in autumn (Fall Festival at the Cold Spring Harbor Fish Hatchery)

Fall Festival at the Cold Spring Harbor Fish Hatchery

Sun, Oct 4

Cold Spring Harbor 20 mi $

Features fishing for kids, live animal encounters, games, and environmental exhibits

Illustration of costumed children and two witches on a lawn with pumpkins, a small tent and orange autumn trees (Vote for Your Favorite Scarecrow! The 36th Annual Scarecrow Competition)

Vote for Your Favorite Scarecrow! The 36th Annual Scarecrow Competition

Oct 3 – Oct 25

Stony Brook 19 mi Free

Stroll the village and cast ballots for your favorite scarecrows.

Illustration of costumed figures near striped booths and pumpkin displays on a grassy town square with orange autumn trees (Halloween on the Green)

Halloween on the Green

Sat, Oct 31

Danbury 19 mi Free

Costume parade, contest prizes, and goodie bags for costumed children.

Illustration of a sunny autumn lawn with pumpkins, hay bales, a small tent, a witch and costumed children under orange trees (The Great Pumpkin Festival)

The Great Pumpkin Festival

Sat, Oct 17

Stratford 14 mi

Features a pumpkin carving contest, costume parade, hayrides, and Public Safety Day.

Castle Hill Farm Corn Maze

Sat, Oct 3

Newtown 18 mi $

Seven-acre corn maze featuring 30 game signs and an observation deck.

Illustration of costumed figures mingling among striped festival booths, pumpkins, and orange autumn trees at dusk (Heritage Farm & Garden Fall Festival)

Heritage Farm & Garden Fall Festival

Sep 26 – Nov 1

Muttontown 23 mi $$

Features farm animals, lawn games, corn maze, and weekend hay rides.

Illustration of a witch in a pointed hat reading a book in an orange armchair beside pumpkins, a lamp and black cats (Beasties and Besties Halloween Festival)

Beasties and Besties Halloween Festival

Sat, Oct 24

Norwalk

Museum-wide haunted festival featuring shadow puppetry and a costume parade.

Happy HalloWINE Run & Walk

Sun, Nov 1

Stratford 12 mi $$

Scenic coastal 5K run and walk featuring wine, beer, and snacks.

Illustration of two small costumed children and a witch among pumpkins, hay bales and autumn trees on a sunny lawn (Creatures of the Night: Lantern Walk and Wildlife)

Creatures of the Night: Lantern Walk and Wildlife

Fri, Oct 9

Smithtown 21 mi $$

Calm, scare-free Halloween walk with live animal presentations and pumpkin lanterns.

Illustration of a fall festival in a town square with a red roofed gazebo, striped booths, pumpkins and orange trees (Tarrytown Halloween Parade & Block Party)

Tarrytown Halloween Parade & Block Party

Sat, Oct 24

Tarrytown 26 mi

Parade featuring over 130 marching groups, floats, and costumed characters.

SUP Witches Festival

Sat, Oct 10

Sleepy Hollow 27 mi $

Costumed witches and warlocks paddleboard on the Hudson River with live entertainment.

Pick-Your-Own Pumpkins

Fri, Oct 2

Yorktown Heights 26 mi Free

Hudson Valley pumpkin patch with free admission and no reservations needed.

Illustration of costumed children carrying pumpkin buckets along a winding path past glowing cottages at dusk (Lyndhurst Trick-or-Treat Weekend)

Lyndhurst Trick-or-Treat Weekend

Oct 17 – Oct 18

Tarrytown 27 mi $

Family-friendly trick-or-treating along estate pathways with optional self-guided mansion exploration.

Illustration of two small ghosts and a witch with a black cat carrying pumpkin buckets on a street of cozy houses at dusk (Shubert Theatre Free Family Fun Day)

Shubert Theatre Free Family Fun Day

Sun, Oct 25

New Haven 25 mi Free

Backstage trick-or-treat walking tour through the Shubert Theatre.

Illustration of two costumed trick or treaters with candy buckets on a dusk street of glowing houses and carved pumpkins (Trick or Treating at Ridge Hill)

Trick or Treating at Ridge Hill

Sat, Oct 24

Yonkers 29 mi Free

Free trick-or-treating at participating shops and restaurants, rain or shine.

Pumpkin Painting

Fri, Oct 2

Old Westbury 28 mi $$

Decorate your own mini pumpkin at the Barn at Orchard Hill.

Illustration of a ghost and a small witch carrying a pumpkin bucket on a sidewalk past glowing porches on an autumn street (Chuck E. Cheese Boo-tacular Halloween Event)

Chuck E. Cheese Boo-tacular Halloween Event

Orange 21 mi $$

Nightly trick-or-treating and 500 bonus E-Tickets for costumed kids.

Illustration of two tiny costumed figures near a flag among tall golden cornstalks, with small farm houses and pumpkins (Wells Hollow Creamery Flashlight Maze)

Wells Hollow Creamery Flashlight Maze

Shelton 16 mi $$

"It's a Bug's Life" themed corn maze

Hall-O-Weekend Fall Festival

Milford 16 mi Free

Free, not-so-scary Halloween weekend for families in downtown Milford.

Illustration of small costumed children and a witch on a sunny autumn lawn with pumpkins, hay bales and orange trees (Suffolk County Vanderbilt Museum Halloween Events)

Suffolk County Vanderbilt Museum Halloween Events

Centerport 16 mi $$

Historic mansion and planetarium hosting Halloween-themed events

Halloween at The Heckscher

Huntington 19 mi Free

Family Halloween celebration at an art museum

NICE Festival

Norwalk Free

Connecticut's premier multicultural festival with two stages and 50+ international vendors.

Illustration of clay figures raising foamy beer steins at wooden tables under a striped tent with pumpkins and leaves (Spooktacular Oktoberfest at Trailside Nature Museum)

Spooktacular Oktoberfest at Trailside Nature Museum

Cross River 14 mi $$

Spooktacular Oktoberfest with Halloween costumes and fall festival fun.

Illustration of a child in a witch costume holding a pumpkin bucket on a leafy sidewalk lined with glowing houses at dusk (New Canaan Halloween Block Party)

New Canaan Halloween Block Party

New Canaan 7 mi Free

Community block party for young trick-or-treaters

Illustration of a witch in an armchair reading a book to small children, with pumpkins and black cats nearby (Danbury Railway Museum Pumpkin Patch Trains)

Danbury Railway Museum Pumpkin Patch Trains

Danbury 18 mi $

Train ride to a pumpkin patch with included pumpkin.

Illustration of a pumpkin patch with many orange pumpkins, a scarecrow, a wheelbarrow, a fence and a red barn at sunset (Wilkens Fruit & Fir Farm Corn Maze and Fall Festival)

Wilkens Fruit & Fir Farm Corn Maze and Fall Festival

Yorktown Heights 26 mi $$

Over 100 years of harvest tradition

Illustration of costumed clay children and a witch playing among pumpkins, hay bales and tents on an autumn lawn (Legend of Sleepy Hollow Family Storytelling Event)

Legend of Sleepy Hollow Family Storytelling Event

Sleepy Hollow 27 mi $$

Costumed storyteller retelling 'The Legend of Sleepy Hollow'

Illustration of a winding path through autumn trees with glowing lanterns and carved pumpkins in purple evening light (Run Wild Halloween Costume Run)

Run Wild Halloween Costume Run

Scarsdale 25 mi $$

1.25-mile forest run with Halloween-themed obstacles

Illustration of a small Ferris wheel, striped tents and a decorated booth with pumpkins on a grassy fairground in autumn (Creepy Crawlies in the Woods)

Creepy Crawlies in the Woods

Larchmont 25 mi Free

Not-too-spooky woodland exploration for families

Family-Friendly Fall Activities this weekend Oct 16–18

Sat17Oct Boo Fest by the BeachMilford

Sat17Oct The Great Pumpkin FestivalStratford

Sat17Oct Lyndhurst Trick-or-Treat WeekendTarrytown

Sun18Oct Walnut Beach Halloween Pet Parade & ContestMilford

thru1Nov Heritage Farm & Garden Fall FestivalMuttontown

thru31Oct Jones Family Farms Pumpkin SeasonShelton

Other Halloween categories near Westport

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

WestportHalloween Food, Drink, and Parties9 parties & tastings

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

WestportHaunted Experiences23 haunted attractions

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

WestportHalloween Movies, Theater, and Entertainment8 shows & screenings

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

WestportUnique Halloween Events8 unique events

About Family-Friendly Fall Activities near Westport

Westport families can find Halloween activities both locally and in nearby towns. Consider the Great Jack O'Lantern Blaze for elaborate displays or the Halloween on the Green in Danbury for a free community event.

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Halloween Events Near Me

36 family-friendly fall activities near Westport

Family-Friendly Fall Activities this weekend Oct 16–18

Other Halloween categories near Westport

About Family-Friendly Fall Activities near Westport

Find Family-Friendly Halloween Fun on Our Map!