Pittsfield Family-Friendly Fall Activities 2026

All aboard for a spooky-fun, family-friendly Halloween Train Ride! Departing from Adams, MA, this festive journey offers scenic views of the Berkshire region with a touch of railroading history. Passengers are encouraged to wear costumes and embrace the holiday spirit...

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....

Step back in time and experience the magic of Albany's All-Hallow E'en Festival, a month-long celebration inspired by a grand carnival from over a century ago. Discover public art, engaging historical exhibitions, and spine-chilling dramatic tours that delve into the...

Join the New York State Museum for a spooktacular Halloween celebration! This family-friendly event features creative art projects, ghoulish games, and intriguing spooky science specimens. Costumes are highly encouraged, culminating in a delightful children's costume parade at 2 p.m. It's...

Join the FASNY Museum of Firefighting for a unique Trunk or Treat: Firefighter Edition! Kids can collect treats from decorated firetrucks and car trunks, play exciting fire safety-themed games, and meet Molly the Museum Dog and local firefighters. It's a...

Lace up your running shoes for Albany's Trick or Trot Pumpkin Run 5K! This festive event winds through a Halloween-decorated Washington Park, perfect for runners and walkers of all ages. Costumes are highly encouraged, adding to the spirited atmosphere. Enjoy...

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,...

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...

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...

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...

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...

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....

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...

Embrace the vibrant colors of fall at Stratton's HarvestFest Weekend. This multi-day celebration offers a perfect blend of live music, stunning scenic lift rides, and delicious food options. Explore the mountain's trails, hike to the summit for panoramic views, or...

Step into a magical world of Wizards & Sorcerers at the MyKingstonKids Halloween Fest & Parade! This family-friendly event features a vibrant parade, immersive workshops, carnival games, and the massive Imagine Park inflatable theme park. Enjoy live performances, costumed characters,...

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,...

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...

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...

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...

Join the Old Stone Fort for a spooktacular afternoon of family-friendly fun at their Trunk or Treat event. Decorated car trunks will be filled with candy and goodies, offering a safe and festive way to celebrate Halloween. Attendees are encouraged...

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...

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...