Boston Moms Getting-Out Guide :: October 2021

Fall is officially here! The leaves are turning, the air is crisp, and Halloween is right around the corner! 

Need some ideas to get out and explore? Boston Moms has compiled a few of our favorite activities happening around greater Boston this October!

October 1-8

Afrobaroque Music & Latin America

October 1
Winchester, MA

Enjoy an amazing evening of rhythmic dances and performances with the talented musicians of Rumbarroco as they swing and groove their way through the African diaspora in Latin America.

The Big E

Through October 3
West Springfield, MA

For 17 days, you can experience everything a state fair has to offer! Concerts, concessions, rides, agricultural shows, a circus, crafts and vendors, and so much more! 

Nantucket Island Fair

October 2-3
Nantucket, MA

Enjoy county fair games and contests, livestock shows, the giant pumpkin contest, a dahlia show, and much, much more! Don’t forget to show off your adorable dog in the pooch parade!

Railfair 2021 Model Train Show

October 2-3
Boxboro, MA

The 56th annual “Railfair 2021” model train show is the perfect event for train enthusiasts! See model railroad displays and exhibits, visit a children’s depot with hands-on exhibits, take train rides, and much more!

After-School Animal Encounters: Radical Reptiles

October 5

Join human museum staffers Javier and Ryan as they lead a 45-minute online program with live reptiles! From snakes to geckos, the world of reptiles is full of fascinating creatures that you will love to “meet!” Pre-registration required. 

October 9-17

Halloween Party Painting Workshop

October 10
Wellesley, MA

Play fun games, have a dance party, paint some festive ceramic pumpkins, bowls, or witch hat-shaped plates at this fun drop-off camp! Costumes are invited but optional. 

The Boston Marathon

October 11
Marathon route (Hopkinton to Boston)

Come cheer on the amazing athletes at the rescheduled Boston Marathon! The division start times are as follows:

Mobility Impaired: 8:50 a.m.
Push Rim Wheelchair: 9:17 a.m.
Handcycles: 9:22 a.m.
Elite Women: 9:32 a.m.
Elite Men & Wave One: 10:00 a.m.
Wave Two: 10:25 a.m.
Wave Three: 10:50 a.m.
Wave Four: 11:15 a.m.

National Fossil Day

October 13

Have you ever wondered what it is like to be a paleontologist? Come find out in this free virtual event! Celebrate National Fossil Day with paleontologists from Harvard, and get an up-close look at fossils in the museum! Pre-registration is required.

Applefest at Wachusett Mountain

October 16-17
Princeton, MA

Applefest is here! Come see more than 100 craft exhibitors, live music, apple pie baking (and eating!) contests, a farmers’ market, and kids entertainment. Plus, peep the peak fall foliage from the SkyRide!

Smoky Chestnut Farm Kids Day

October 17
Norton, MA

Pick a pumpkin from the pumpkin patch to paint and decorate, get your face painted, and get your picture taken with the beautiful ponies! Enjoy fresh made popcorn and many yummy homemade treats. The farm will be decorated with friendly ghosts and goblins!

October 18-25

Smolak Farms Fall Festival Weekends

Weekends through October 31
North Andover, MA

Enjoy outdoor stories and crafts, themed hayrides, walking tours, and apple picking — and don’t forget to visit the animal area!  

Greenway Play Sessions: Bubbles, Games, and More

October 21

Come have a blast at freeplay sessions at Auntie Kay and Uncle Frank Chin Park on Thursdays from 5-7 p.m., featuring books, games, and more! Support local businesses and spend your evening playing outside by the Greenway PlayCubes!

Head of the Charles Regatta 2021

October 22-24
Cambridge, MA

Watch rowing teams compete from all over the country, and take in the sights of autumn along the banks of the Charles River in Cambridge.

Playtime Theatre Shows by Concord Youth Theatre

October 23
Concord, MA

Come watch your favorite stories come to life at Concord Youth Theatre! Perhaps you can even share your own special talents and participate with a sing-a-long! Shows begin at 10:30 a.m. on Saturdays! 

Watson Adventures’ Haunted Tales: The Online Halloween Family Scavenger Hunt

October 23-31

Do you want to Zoom with a ghost? Kids and adults can team up to explore real places that are said to be haunted in this unique online scavenger hunt! Follow a trail of clues across eerie websites and learn the tales of the ghosts who linger there while you search for answers to tricky questions!

October 26-31

Salem Haunted Happenings

Through October 31
Salem, MA

What better way to celebrate Halloween than to visit a Halloween festival? From family-friendly activities to shake-in-your-pants terror, Salem has all the festive frights you could dream of!

Hanson’s Haunted Farm and Hayride

Friday-Sunday through October 31
Framingham, MA

Hanson’s Haunted Hayride has been a local tradition since 1993! If you are looking for a thrill, come take a ride on the Haunted Hayride!

Tricks and Treats: Spooky Science at the Waterworks Museum

October 30

Learn the science behind some spooky effects, create crafts, play fun Halloween-themed games, and check out the “Spooky Science of Magic” show at this fun family event! 

Hollowed Harvest: Wicked Labyrinth

Through October 31
Salem, MA

The Hollowed Harvest brings to life more than 7,000 incredible jack-o’-lanterns, creating stunning landscapes and larger-than-life displays! Guests of all ages will love the creativity and beauty of this fun (and not spooky or scary!) family event.

Deanna is a mom of five (yes, five) children, who lives in Brockton with her small circus of kids, her husband, their dog Penny, and a few cats. Her life is loud, energetic, mostly fun, often gross (did she mention four of those kids are boys?), and she wouldn't have it any other way. In between carting kids to school, baseball, gymnastics, guitar, dance, track and field and every other kid activity known to mankind, she works as a school bus driver for the city of Brockton, and is the Director of Religious Education at the Unity Church of North Easton, a Unitarian Universalist congregation. Deanna also holds degrees in Elementary Physical Education and Dance Education, which she plans to put back into use one day. At parties, Deanna can often be found hanging out with family pets. She follows her children around with a camera like the paparazzi, is pretty sure that 97% of her blood stream is made of coffee, and her laundry is never done. You can also find her blogging at


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