• Skip to primary navigation
  • Skip to main content
  • Skip to footer

New England for Families & Boston Kid Friendly

Family Friendly Fun - Boston, Massachusetts - Local and Visiting Families.

  • Home
    • Local or Tourist? How to get started with Boston Kid Friendly!
    • MBTA Stations
  • About
  • Now Hiring!
  • Recent Posts
  • Current field trip guide
  • Shop

Massachusetts Fall Festivals and Events

by New England for Families Editor Leave a Comment

7 shares
  • Share
  • Tweet

If you’re looking forward to all the Massachusetts fall festivals, fairs and destinations to explore, you’re going to love all of these family-friendly options. Not only are they are all fun engaging for all ages, but they’re also affordable and worth the travel time to explore.

Now that the fall season is coming up, it’s time to start doing a bit of research on all the fall festivals in Massachusetts. And honestly, is there any better time to be out and about exploring than during the fall months? The leaves are turning, the crisp air smells glorious and there’s just so many awesome activities and fairs just waiting to be explored.

This year is the year to get out and about and find out where all the fun destinations in Massachusetts are. And luckily, I’ve rounded up some of the best fall festivals and outings for you right here!

Fall Festivals and Fairs and Destinations in Massachusetts

Get out and enjoy the beautiful weather, fall foliage, and apple cider donuts at some local Massachusetts Farms! This is not only a great way to enjoy time with the family, but also a means to support local business and farms! So whether you’re looking for mazes and hayrides or just a pumpkin patch, there are Massachusetts fall festivals and events throughout the state. Here are some options to help you find a location that suits your family’s needs the best! These are just a few of the fun fall festivals, fairs, and destinations to visit this fall! Mark your calendars so you don’t miss any of the fun.

Mystic River Celebration

Saturday, September 21, 2019

A great festival of the arts for all ages. Spend the day checking out all the vendors, listening to live music and chowing down on some delicious food. Bring a blanket and sit and just enjoy those tunes or taste-test your way through the venue. It’s perfect for all ages to kick back and enjoy.

What the Fluff?

Saturday, September 21, 2019

Everyone knows what fluff is, right? And what a glorious way to celebrate it by attending the fluff festival with your family and friends. Arrive hungry because there are tons of fluffy treats that are certain to be delicious. Join over 20,000 other attendees in exploring everything that this festival has to offer.

HONK! Festival of Street Bands

October 11-13, 2019

Get ready to see street band after street during this 3-day festival. And most times, there aren’t even any stages involved. Bands will just line up in various locations and stary laying out the tunes. Stand and tap your feet along to the beat or even bust out in some dance moves. When it comes to this music festival, there’s no wrong way to show your appreciation for the sounds.

Harvest Festival

October 12-13, 2019

Spread out over 15 acres, this is one Massachusetts festival that you don’t want to miss. The entire venue is geared towards families and children and there are literally over a hundred different vendors that are showcasing their products and homemade goods. Gather up the kids and stay for the hayride and pony rides…this is one fun festival that you literally won’t want to miss.

Pumpkin Float at Frog Pond

October 19, 2019

As you can probably guess, this whole day is about pumpkin everything! You can even bring in your own small pumpkin that you’ve already carved to be added to the frog pond decorations.

With everyone attending and bringing carved pumpkins, they’ll be floating on Frog Pond all night long! And don’t forget to stay and join in on all the other fun treats and tricks that the night has to offer.

This FREE family event is a great way to celebrate your love of Halloween just a tad bit earlier than planned.

As you can see, Massachusetts offers so many fun family-friendly festivals and activities during the fall months. With just a little bit of research, you can literally find a fair or festival to attend every single weekend. From farm animals to pumpkins, you are certain to enjoy hour after hour of festival fun!

More places to go outside the immediate Boston Area.

Massachusetts fall festivals list with a state map of them. Includes hayrides, corn mazes, pumpkin patches, and more.

Enjoy Massachusetts Fall Festivals & Events with the Family!

Boston Hill Farm – Andover, MA

Go apple and pumpkin picking and enjoy the Boston Hill Fall Festival. They have great food and entertainment including games, a petting zoo, and hayrides. They serve Richardson’s ice cream and start hay rides as early at 11am! While they’re open year round from 9am to 6pm, don’t forget to stop by for the fun festival this fall!

Wilson Farm – Lexington, MA

In the month of October, Wilson Farm has some exciting opportunities for the family to participate in. Everything from costume contests to haunted hayrides! Even attend their gingerbread house workshop to prepare for the holidays. Check out current and upcoming fall events in Lexington on their site.

Connors Farm – Danvers, MA

Enjoy a 7 acres corn maze in Danvers, watch shows, pick pumpkins, and play games all at Connors Farm. See everything you can do  on their farm attractions age guide. If you’re going without kids or have older children, check out Hysteria at Danvers that is open in October. It includes zombie paintball, a haunted farm, and a flashlight maze (which is actually suitable for all ages!).

Cedar Hill Farm – Amesbury, MA

You’ll find hayrides, pumpkins, and lots of fun visiting Cedar Hill in the Fall. Check out their event page and sign up for their mailing list to know when new opportunities arise to visit the farm with the family.

Lookout Farm – Natick, MA

Have your kids ever gone on a camel ride in Boston? That’s just one of the fun activities your family can do while visiting the Belkin Family Farm. Enjoy some tasty cider, get your faces painted, and more!

A few other Massachusetts Fall Festivals & links to check out. View the Fall Festival Map I have compiled below to see where each one is located in Massachusetts!

Harvard Square Oktoberfest & HONK
Union Square Fluff Festival
Davis Mega Maze
West End Fall Festival
Sturbridge Harvest Festival
Blackstone Canal Fest
Wachusett Apple Fest
Newburyport Fall Harvest Festival
Berkshire Botanical Garden Harvest Festival
Cape Cod Cranberry Harvest Celebration
South Shore Corn Festival

Don’t see your favorite fall festival in Massachusetts? List it and link to it in the comments!

Take a day trip from Boston to the Newbury area to enjoy the sunflowers.      Kid Friendly Halloween Events in Boston   Boston, MA fall family travel guide

Filed Under: Local Family Events and Attractions Tagged With: Events and Attractions, Fall, Farms, Massachusetts

Previous Post: « Where to picnic in Boston: Top picnic spots on the T map
Next Post: How to plan the ultimate fall bucket list in New England + win prizes! »

Reader Interactions

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

Footer

Latest Posts

  • How To Weave Together A Field Trip To Bootts Mills Cotton Museum That Will Make An Impact
  • Silent Visitors Miss Valuable Stories: Step back in time at the Wright Museum of WWII
  • Nashua’s one room school house is an informative treasure

join the boston kid friendly event group

  • DONATE
  • Blog
  • Shop
  • Cart
  • Write or photograph for us!

Copyright © 2025 · Foodie Pro & The Genesis Framework

7 shares

Subscribe to the Newsletter!

Get updates when a new podcast and video goes live and for occasional updates to events you can't miss. Plus, upon signing up, you'll get an awesome activity pack for free!

x