Westport Family-Friendly Fall Activities 2026

Stepping Stones Museum for Children hosts the annual Beasties and Besties Halloween Bash, a spooktacular event for all ages. This museum-wide haunted festival features a Monster Mash dance party, classic carnival games, and creative craft stations like pumpkin decorating and...

Discover the vibrant culture of Norwalk, CT at the NICE Festival on Saturday, October 4, 2025. This free, family-friendly event at Oyster Shell Park features two stages with over 24 live performances, showcasing diverse traditions and genres. Explore over 50...

Norwalk's Washington Street comes alive for the annual Halloween Nightfair, a vibrant celebration transforming the area into a festive hub. From afternoon delights like pumpkin painting and a Trick or Treat Trail to evening entertainment and glowing lights, the event...

The New Canaan Halloween Block Party is a cherished annual event where the town's youngest residents and their families gather to celebrate Halloween. Held on Elm Street, this block party provides a safe and exciting environment for children to show...

Embark on a delightful Halloween adventure at Heckscher Farm, a special members-only event. Children aged 3-10 can explore the farm, solve a fun Halloween riddle by visiting themed stations, greet beloved animal friends, and create a craft. Upon completing the...

Get ready for a spooktacular time at the Fourth Annual Stamford Moms Halloween Candy Crawl! Families can enjoy a free event filled with trick-or-treating at participating retailers and vendor tables. Kids can meet beloved characters like Elmo and Cookie Monster,...

Experience an authentic farm adventure at Warrup's Farm this fall. Visitors can pick their own pumpkins straight from the vine, enjoy a classic hayride, and browse the farm stand for local apples, cider, honey, gourds, and more. It's a perfect...

Get ready for a Spooktacular Oktoberfest at Trailside Nature Museum! This annual event combines Halloween thrills with fall festival fun. Kids can enjoy trick-or-treating, a costume contest, and crafts, while everyone can experience hayrides and engaging presentations. The Oktoberfest section...

Get ready for a spooktacular Halloween celebration at the Walnut Beach Halloween Parade! This family-friendly event features candy, costumes, and dancing with a DJ. Don your best costume for a chance to receive free ice cream from Walnut Beach Creamery,...

Bring your furry friends to the Walnut Beach Arch for a delightful Halloween Pet Parade and Contest. Dogs can strut their stuff in their most creative, scariest, or funniest costumes for a chance to win prizes. A panel of judges...

Get ready for a spook-tacular day of Halloween family fun at the shore! Dress up in your best costume and join the festivities at Walnut Beach. They'll have trick-or-treat stops throughout the district, enchanting horse and carriage rides, live entertainment,...

Get lost in the "It's a Bug's Life" themed corn maze at Wells Hollow Creamery. Brave the Flashlight Maze on select evenings for a thrilling, dark adventure. During the day, enjoy the "Corn Maze Challenge" and visit the farm animals....

Step into a world of Halloween enchantment at the Suffolk County Vanderbilt Museum. This historic estate transforms into a hub of seasonal activities, offering a blend of spooky fun and educational exploration. Discover the mysteries of the cosmos at the...

Join the Milford Trick or Trot for a festive Halloween celebration featuring a 5K run/walk and an outdoor family movie night. This community event supports the Beth-El Center, helping to combat hunger and homelessness. Don your best costume for a...

Join the Downtown Milford Business Association for their annual Hall-O-Weekend Fall Festival, a free, not-so-scary Halloween celebration. Families and children can enjoy a weekend of costumes, adventures, and treats. Activities include an outdoor movie night, a costume parade, kids' yoga,...

Lace up for the 14th Annual Milford Trick or Trot 5K Run/Walk! This festive event supports The Beth-El Center, aiding those experiencing homelessness. Participants can choose the 5K run/walk or the free Kids Halloween Dash. Don your best costume for...

Immerse yourself in the autumn spirit at Jones Family Farms' Pumpkin Season. Wander through vast pumpkin fields to select your perfect gourd, or enjoy a scenic hayride through the picturesque landscape. Discover fun photo opportunities, educational displays, and a charming...

Get lost in the expansive seven-acre corn maze at Castle Hill Farm, featuring a new, unique design each year. Navigate through 30 game signs, or take a break at the observation deck. Special 'Flashlight Maze' nights offer a thrilling after-dark...

Join families for the 33rd Annual Halloween on the Green, a spirited community event featuring a children's costume parade with prize categories for originality, scariness, and cuteness. Attendees can enjoy local vendors, music, a photo booth, and kid-friendly activities. Goodie...

All aboard 'The Husking Bee' for a delightful fall adventure! This beloved annual event offers families a charming 20-minute train ride to a special pumpkin patch. Passengers can pick out their own pumpkin, enjoy local apple cider and cookies, and...

Families and children are invited to don their costumes for a delightful Halloween celebration at The Heckscher Museum of Art. This event offers a chance to create a spooktacular art activity and take home a festive treat, making for a...

Experience the magic of autumn at Harvest Moon Farm and Orchard's Fall Festival. This two-month celebration offers a delightful escape with live country music, a sprawling pumpkin patch, and delicious seasonal treats. Families can enjoy apple picking, hayrides, and a...

Experience a delightful Fall Festival at the Cold Spring Harbor Fish Hatchery & Aquarium. This family-friendly event offers a variety of activities including fishing, exciting animal encounters, live music, and engaging games. It's a perfect way to celebrate the autumn...

Discover a not-so-scary Halloween celebration at the Westchester Children's Museum. This family-friendly event offers a playful learning environment with interactive exhibits and special programs. Enjoy daily activities and themed weekend events throughout the fall season.

Join the ultimate Halloween celebration at Chuck E. Cheese Orange for their Boo-tacular event! Enjoy safe, nightly trick-or-treating with Airheads® candy, spooky shows, and delicious seasonal treats. Kids in costume receive 500 free tickets, and special Halloween menu items like...

Bring little ghosts and goblins for a spooktacular self-guided Trick or Treat adventure within the historic Main House. Kids can follow a treasure map through each room, collecting treats, prizes, and learning fun facts about the Coe family and their...

Immerse yourself in the autumn spirit at the Heritage Farm & Garden Fall Festival. Wander through a captivating corn maze, get creative with pumpkin decorating, and delight in the company of friendly farm animals. Capture memories with abundant photo opportunities...

Discover the charm of the Seymour Pumpkin Festival, a beloved tradition since 1965. This family-friendly event offers a delightful day out with a vibrant mix of craft vendors, diverse food options, live entertainment, and engaging activities. Explore themed areas like...

Experience a unique Halloween celebration at the historic Shubert Theatre with a free family fun day. Patrons can enjoy a self-guided backstage tour, complete with trick-or-treat stations along the way. Children are encouraged to wear their costumes for the festivities.

Embark on a not-too-spooky adventure through Sheldrake's woods this Halloween season. Join an engaging outdoor exploration to discover fascinating 'creepy crawlies' along the trails, from insects to bat houses. This family-friendly program offers a fun and educational way to connect...

Get ready to unleash your inner wild side at the Run Wild Halloween Costume Run! This exciting 1.25-mile forest adventure features a thrilling obstacle course with challenges like alligator pools, balance beams, and rope swings. Participants are encouraged to don...

Discover the charm of Wilkens Fruit & Fir Farm's annual fall festival. Wander through their impressive corn maze, a highlight for many visitors. Engage in the classic autumn activity of picking your own apples and pumpkins straight from the source....

Dive into the heart of Halloween at Sleepy Hollow Country, where the legend of the Headless Horseman comes alive. This region offers a packed schedule of spooky events throughout October, including the dazzling Great Jack O'Lantern Blaze, atmospheric cemetery tours,...

The 23rd annual Tarrytown Halloween Parade returns on October 25th, 2025, bringing spooky fun to the village. Participants can register to march as individuals, groups, or on floats for a chance to win prizes. Following the parade, a lively Block...

Experience the magic of the witching season at the 6th Annual SUP Witches Festival in Sleepy Hollow, NY. This spellbinding event features witches paddling on the Hudson River, live music from local bands, a marketplace of witchy vendors, and delicious...

Step into the legendary world of Sleepy Hollow for a captivating family storytelling event. Storyteller David Neilsen, in full costume, brings Washington Irving’s 'The Legend of Sleepy Hollow' to life with a 25-minute performance using the author's original language. This...

Prepare to be amazed by The Great Jack O'Lantern Blaze, an immersive Halloween spectacle featuring over 7,000 hand-carved, illuminated pumpkins. Wander through themed lands, discover iconic New York landmarks sculpted from gourds, and marvel at a 'wickedly' fun emerald-hued dreamscape....

Experience a charming fall adventure at the Shore Line Trolley Museum's Pumpkin Patch. Ride historic trolleys through scenic salt marshes, observe local wildlife, and explore a collection of vintage transit vehicles. This unique event offers a glimpse into the past...

Lace up for the Halloween 5K & Monster Dash! This event features a fast, flat USATF Certified 5K course and a fun Monster Dash for kids 12 and under. Participants can compete for awards in various age groups, and a...

Celebrate the autumn season at Old Westbury Gardens with a delightful array of family-friendly activities. Engage in creative pumpkin painting, embark on a magical 'Whimsical Wizard School' adventure, or enjoy charming storybook strolls and engaging puppet shows. Explore the vibrant...

Get into the Halloween spirit at LEGOLAND Discovery Center Westchester's Brick-or-Treat Monster Party! Families with children ages 3-12 can enjoy a monster takeover with themed activities, including brewing magical potions at the Potion Kitchen and hunting for LEGO® monsters in...

Celebrate the season at Hicks Nurseries' 50th Annual Fall Festival! This beloved event offers a full day of family fun with an All-Access Wristband, including unlimited hay maze adventures and three creative crafts. Enjoy free lawn games, mini golf, and...

Don your most daring costume and join the 36th Annual Nyack Halloween Parade, celebrating the 50th Anniversary of 'The Rocky Horror Picture Show'. This vibrant event features a parade, a flash mob 'Time Warp' dance, and a special screening of...

Join the annual Halloween Spooktacular for a wicked good time! This family-friendly event features special witch performances with meet-and-greets, trick-or-treating throughout the center, and fun inflatable attractions for kids. Costumes are highly encouraged for this day of Halloween excitement.

Experience a magical day at Untermyer Gardens with their Family Fun Day event. This unique occasion allows visitors to picnic inside the stunning Walled Garden, a privilege only offered on this special day. Enjoy a captivating magic show by Mystique,...

Join the annual Boomer's Boo Bash, a beloved Halloween celebration hosted by Quinnipiac University for the local communities. This family-friendly event invites local businesses, student organizations, and student-athletes to share in the festive fun on the university's Quadrangle. Attendees can...

Join the Ghoul Scout Halloween Happenin' for a night of spooky fun that glows like gold! This family-friendly event features a haunted trail, costume fashion show, pumpkin painting, and exciting games. Enjoy a s'mores bar and Halloween movies as the...

Bring your little goblins and ghouls for a safe and fun trick-or-treating experience at The Shoppes at East Wind. This family-friendly event offers a secure outdoor environment for children to enjoy Halloween festivities. The carousel will also be open, adding...

Visit Harris Hill Farm for their annual pick-your-own pumpkin patch, open weekends throughout October. They offer a fantastic selection of large, jack-o'-lantern style pumpkins, alongside a variety of other fall crops like butternut squash, spaghetti squash, and decorative gourds. It's...

Join the fun at Palisades Center for a delightful trick-or-treat event perfect for families. Children can gather candy and enjoy festive activities in a safe, indoor environment. It's a wonderful opportunity for kids to showcase their costumes and celebrate Halloween.

Get ready for a spooktacular Halloween at the farm! This family-friendly event features trick-or-treating at numerous stations, unlimited wagon rides, and a fun-filled corn maze. Kids can enjoy crafts and games, while adults can savor treats from local food trucks....