South Windsor Family-Friendly Fall Activities 2026

Foster Family Farm offers a quintessential fall experience for all ages. Navigate through their impressive corn mazes, take a scenic hayride, and select the perfect pumpkin. For an extra thrill, experience the Night Maze on select Saturday evenings. It's a...

Experience the charm of Farmer's Hayrides at a picturesque working dairy farm in Broad Brook, CT. Enjoy scenic hayrides, hand-feed dairy cows, explore a sunflower maze, and pick your own pumpkins. The farm is beautifully decorated with fall elements, creating...

Embark on a charming trolley adventure to a vibrant pumpkin patch, where each child can select their own complimentary pumpkin. Upon returning to the museum, enjoy creative pumpkin decorating, fun in the corn box, and explore the outdoor harvest play...

Experience the East Hartford Annual Fall Festival, a beloved community celebration. This event features a giant inflatable corn maze, pumpkin decorating activities, and a variety of games and attractions for all ages. Browse offerings from local vendors, crafters, and non-profit...

Join the Halloween Stroll 2025 in West Hartford for a spooktacular morning of family fun. Little ghouls and goblins can enjoy trick-or-treating at outdoor storefronts and the Town Hall Lawn. The event features live music from 'Sunny Train' and a...

Celebrate the autumn season at Fair Weather Growers' annual Fall Festival and Corn Maze. This beloved tradition offers a full day of family fun with activities like a challenging corn maze, scenic hayrides, and a pumpkin patch. Kids will love...

Visit Riiska Brook Orchard for a quintessential fall experience where you can pick your own pumpkin straight from the patch. Enjoy a scenic drive through their beautiful orchard to discover the perfect pumpkin for your Halloween decorations or festive displays....

Celebrate Halloween with a fun-filled day at the Springfield Museums! Kids can wear their costumes and go trick-or-treating in the galleries, collecting treats from various stations. The event features face painting, a craft station to decorate trick-or-treat bags, and giant...

Join Klingberg Family Centers for a fun-filled Trunk or Treat event! This free community gathering offers a safe and exciting way for families to celebrate Halloween. Children can enjoy complimentary face painting, tattoos, and games, with the first 250 kids...

Get ready for a spooktacular Halloween adventure at the West Springfield Trick or Treat Trail! Children are invited to don their favorite costumes and embark on a delightful quarter-mile walk along the Bagg Brook Trail. Along the way, they'll discover...

Join the ghoulishly fun Halloween Mall-O-Ween at Holyoke Mall for a safe, family-friendly evening. Collect treats from participating businesses throughout the mall. Don't miss the social media costume contest with categories for most creative and best group costumes, offering a...

Join the Children's Museum at Holyoke for their annual 'Trick or Treat at CMH!' event. This magical afternoon promises a delightful experience with trinkets, prizes, games, and activities. Select museum exhibits will be transformed with festive Halloween decorations, and costumed...

Celebrate the harvest season at Lyman Orchards' Corn Maze & Cider Donut Harvest Music Festival. This family-friendly event features a unique "Pizza Pie" themed corn maze filled with facts about Connecticut's pizza culture. Enjoy live music from local bands, explore...

Experience the quintessential fall tradition at Lyman Orchards' Pick Your Own Pumpkin Patch. Nestled on 200 acres overlooking the Connecticut River Valley, they offer a delightful outing for all ages. Select from a wide array of sugar and carving pumpkins,...

Visit Fletcher Farm, recognized as the #1 pumpkin patch in Massachusetts, for an authentic fall experience. This multi-generational dairy farm offers a charming pumpkin patch and classic hayrides, perfect for family fun. Explore the farm stand for fresh local produce,...

Experience the charm of Cheshire's "Pumpkin Church" as St. Peter's Episcopal Church transforms into a vibrant pumpkin patch each September and October. This cherished 20-year tradition offers a fantastic opportunity to select the perfect pumpkin while supporting indigenous growers and...

Odetah Camping Resort hosts its 'Happy Hauntings Weekend,' a celebration filled with spooky fun. Activities include Firepit Fridays with s'mores, a final Bingo night, and creative pumpkin painting. Campers can showcase their Halloween spirit through site decorating and costume contests,...

Get ready for a frightfully fun time at The Carle's Halloween BOO-k Bash! This family-friendly event invites guests to don their costumes for a day filled with festive fall programming. Enjoy a trick-or-treat scavenger hunt, seasonal films, and a special...

Experience the magic of Pumpkin Passage, a family-friendly Halloween event at The Dinosaur Place. Wander through a dazzling trail of lights featuring glowing dinosaurs, pumpkins, and mythical creatures. Enjoy live entertainment, inflatable attractions, marshmallow roasting, and delicious food truck offerings....

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 historic Florence Rag Shag Parade, the nation's oldest continuously running event of its kind. This cherished Halloween tradition begins at Trinity Park with a 6 PM step-off, marching down Main Street to conclude at the Florence Civic Center....

Experience the quintessential New England fall at March Farm! Visitors can pick their own apples and pumpkins, get lost in a sprawling 5-acre corn maze, and enjoy scenic tractor rides. Live music and delicious food trucks add to the festive...

Bishop's Fall Festival offers a quintessential autumn experience with apple picking, a unique New Haven Pizza-themed corn maze, and a vibrant pumpkin patch. Families can enjoy a wide array of activities, including jump pads, a corn pit, and pedal carts,...

Experience the charm of a tenth-generation family farm at Averill Farm's pick-your-own pumpkin patch. Wander through their scenic 30-acre orchard, selecting the perfect apples and pears. Discover a delightful array of local goods, including fresh cider, donuts, jams, pumpkins, gourds,...

Experience a spooktacular evening at New London Halloween Town, a family-friendly event at the waterfront park. Enjoy trick-or-treating, a costume contest for kids, and lively roaming entertainment. The event also features performances by Luis Pabon Dance Arts Centre and a...

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...

Join Olde Mistick Village for their annual Halloween Trick or Treat Candy Handout. This beloved, safe, and family-friendly event invites children and their families to collect treats from participating village shops. It's a cherished alternative for Halloween fun, offering a...

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 "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....

Join the WooSox for a free indoor trick-or-treat event at Polar Park. Families can enjoy trick-or-treating around the park, pumpkin decorating, candy bag creation, and various Halloween games. It's a fun-filled afternoon with activities for all ages, plus food and...

Bring the little ones to Polar Park for 'Boo in the Woo for Kids,' a family-friendly Halloween celebration. This event transforms the ballpark into a festive wonderland with age-appropriate spooky fun. Kids can enjoy a variety of activities, games, and...

Experience the West End Creamery's Fall Festival & Corn Maze, a 28-acre celebration of autumn fun. Get lost in a 5-acre corn maze honoring American history, enjoy included attractions like pedal carts and a cow train, and take a scenic...

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,...

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...

Wojcik's Farm offers classic fall fun with a sprawling five-acre corn maze and scenic tractor-driven wagon rides. Challenge yourself to find three hidden checkpoints within the maze for a chance to win cash prizes. Relax and enjoy the picturesque countryside...

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...

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 into the Halloween spirit at 92 PRO-FM's Spooktacular event! Meet Kim Zandy from 92 PRO-FM, snag some cool swag, and get a chance to win tickets to see Maroon 5 live in concert. It's a fun-filled afternoon for all.