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Family Fall Fun in Massachusetts

The cooler weather has arrived and with it, all the fall festivals and activities are here too. My daughter has started her list and is planning out our fall activities with her favorites. She’s my lover of all things fall. She wants to wear leggings and warm sweaters and to drink hot apple cider. She can’t wait to pick apples and carve pumpkins. Of course, she wants Halloween to come. However, don’t ask about a costume just yet. Fall is definitely her favorite time of year.

Visit a Farm for Fall Picking

Apple picking, pumpkin picking, and a corn maze. Is there anything more that screams fall than that? Yes, of course, don’t forget the cider donuts! These are a must-visit on our fall schedule. My family loves it when we pick apples because they know what comes next – apple pie, baked apples, apple cranberry crisp, and apple bread! Yes, the baking will commence soon. Now that we live north of Boston we’ve been going to Smolak Farms for our apple picking. The farm has a great variety of apples to pick. We always end up with so many bags full. Of course, the day wouldn’t be complete without getting our pumpkins, trying our hand at the corn maze and getting cider donuts! Ok, and ice cream for our daughter with celiac disease.

apple picking in fall
We love apples

King Richards Faire

Have you ever attended a Renaissance Festival? King Richards Faire is in Carver, Massachusetts and is open weekends and Columbus Day until October 20, 2019. Well, if you are into jousting, fairy circles, mud fights, and eating turkey legs, this is the place for you. My brother and his friends dress in costume to really get into the whole experience. But even if you go in street clothes you will get caught up in the atmosphere. When you visit be sure to try your hand at knife or axe throwing. Test your skill at the dragon joust or crusader’s crossbows. However, don’t miss seeing the King’s tournament and having your kids participate in knight school. This faire is fun for the whole family.

jousting in the fall
Jousting: photo by King Richards Faire

Light a Pumpkin on Frog Pond

Who doesn’t love jack-o-lanterns? This festival takes place on October 19, 2019, from 5-8:00 pm at the Frog Pond in Boston Common. You bring an 8″ or smaller carved pumpkin to Frog Pond. Then the organizers light the pumpkin and float it on the pond. Even if I didn’t have children I’d go to think event. I think seeing all the jack-o-lanterns floating around the pond will be magical. They will also have fall activities, treats, and crafts for the kids.

Pumpkin fest in the fall
Floating pumpkins on Frog Pond. Picture by Frog Pond Common

Take a Cranberry Tour or Attend the Nantucket Cranberry Festival

Where would Thanksgiving Dinner be without cranberry sauce? Lost in our house. We make 2 different kinds of cranberry sauce. One with oranges and one without. I’m a purest but my husband’s family loves the orange one. If you don’t already know, to harvest the cranberries the farmers flood the fields. They get to wade through in galoshes to work the bogs. Don’t worry, on this tour you won’t get wet but you will see a working cranberry farm. Cranberry Bog Tours fill quickly so it is best to call prior to heading down to the cape. They also have a farm stand and have cranberry honey. I wonder how wonderful that is?

cranberry harvest in fall
Harvesting cranberries. Photo by Massvacation

Nantucket has its very own Cranberry Festival. Here you will see a demonstration of harvesting, or you can try your hand at harvesting the cranberries. There will also be sack races, face painting, tug of war and music. Of course, don’t forget to try some tasty treats and get all the cranberries you need here.

Old Sturbridge Village

Old Sturbridge Village is the largest 19th-century living museum in New England. We’ve been there for a reenactment festival which was spectacular. They reenacted a civil war battle with the bugle call, cannons, bayonets, gunfire, horses charging you name it they had it. It was marvelous. The whole village is so enjoyable to see whether during an event or not the village comes alive. The craftspeople and characters in the village make the experience. This fall once again they are presenting “The Sleepy Hollow Experience”. This is a musical experience like no other for you are guided through the village as the play unfolds. It sounds like an absolutely thrilling time.

Picture by Old Sturbridge Village

Harvard Square Oktoberfest & HONK! Parade

Think Oktoberfest with a fun, loud, musical band parading through the streets and you have this festival. Harvard Square will be taken over this fall by HONK festival. There will be 6 beer gardens along with fabulous food from all over the world. As well as sidewalk sales, arts, crafts, and samples. Don’t miss the numerous stages around the square with different musicians on each. The HONK parade should make it to the square around 1 pm. Participating by dancing, honking, bike riding, and stomping of your feet are all encouraged during this parade. Come out on Oct 13th from noon to 6 pm and be a part of this fun festival.

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Going to the parade in costume is always fun, but having a horn to make noise is a MUST!  Don’t go empty handed!

Oktoberfest in fall
Oktoberfest and HONK festival. Picture by HONK fest.

Hiking in the Berkshire Mountains in Fall

The Berkshire Mountains are beautiful any time of year but especially in fall. The Appalachian Mountain Club has some amazing hikes outlined for you to enjoy. There are 3 listed that will give you some stunning vistas and lovely scenes. The Bash Bish Falls hike is on the border of New York State. From Massachusetts, there’s an easy stroll to see this impressive waterfall or from New York a strenuous loop hike. The second hike is the Jug End Trail which is great for young families. Make sure to bring your binoculars as this is a great hike to view birds. In the winter months, you can even snowshoe and go cross-country skiing on this trail. The third hike is the Pine Cobble trail to East Mountain. This hikes popularity is due to the stunning summit views from the overlooks into Hoosic Valley and the Greylock Range.

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While you are in the region look up a geocache to find.  Who knows it might even be on your hike?  And as always stay hydrated while hiking.  Our family all have their own ‘water’ backpack to encourage drinking while hiking. 

fall leaves in the Berkshires
The Birchshires in the fall. Picture by Massvacation

Wellfleet Oyster Fest

This is a celebration of Wellfleet’s famous oysters, clams and shellfish. Come with an empty stomach because you will want to sample all the delicious food. There will be everything from a raw bar to chowders and stuffed clams to other New England favorites. I’m sure you will want to try it all. For the kids, there will be arts and crafts, a fun run and obstacle course. For the adults, there will be New England brews and wine along with many local artists to peruse. And you can not leave the festival without seeing at least one round of the Oyster Shucking Contest. Feel like you can give a local a run for their money? Well, enter the contest and put your stake in the game!

Oyster on the half shell
Raw Oysters. Picture by Massvacation

Plimoth Plantation

A visit to Plimoth Plantation is a great way to celebrate the fall season. They have a salute to fall weekend in October with demonstrations of cooking, gardening, and crafts. As well as a recreation of a 17th-century military muster which I’m sure will be impressive. Area’s of the plantation to see include the English Village to the Wampanoag Homesite to the Plimoth Grist Mill. You can also attend the Thanksgiving Day Homestyle Buffet at the plantation.

Plimoth Plantation in the fall
English Village. Picture by Plimoth Plantation

Salem Witches

You can’t talk about fall and not think of Salem and the famous witch trials. Whether you like witches, and goblins and ghouls or just the lighter side of Halloween Salem is the place to be. For the whole month of October, there are festivals, street fairs, walks, sightings and encounters. The Grand Parade is on October 3rd and events continue from there. For kids, I would recommend the Salem Kids Tours. You will learn some interesting facts about Salem, the witch trials as well as some trivia. However, there are so many to choose from you should look over the website to select what’s best for your family.

Bewitch statue Salem Massachusetts
The Bewitch Statue in Salem

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fall fun

What fall festivals and activities are you and your family going to enjoy this year? I can’t wait to go apple picking and I’m up for a weekend on the cape for Oyster fest.

This Post Has 42 Comments

  1. Jennifer

    Thanks, I enjoyed this post. My great-great grandfather was born in Massachusetts, then came here. Here, fall is Autumn. When, I was young, we would go to the gardens, and run and play in the fallen autumn leaves. I love all the colours of the leaves.

    1. Leeanne

      It’s so nice that you have great memories of those times when you were little.

  2. Jay

    Very detailed. My mom is going to Mass really soon. For sure sharing this with her for when she meets up with family there.

  3. Cynthia

    This is a great post! I love fall and these activities sound like so much fun. I live in Florida so there are so many of these that I would love to attend. The Nantucket Cranberry Festival seems like it would be so interesting! Thank you for sharing!

    1. Leeanne

      Yes, I agree Cynthia, the cranberry festival does sound like a lot of fun.

  4. Jordan

    I love all things Fall, including apple picking and pumpkin carving. I’ve never been to a cranberry farm, so that’s intriguing to me. I’d love to try harvesting. Also, the Birchshires looks absolutely stunning!

    1. Leeanne

      My husband would be right there with you in the bogs trying his hand at harvesting. I imagine it’s fun but tough work. And yes, the Berkshires are stunning in autumn.

  5. Pam

    Wow! So many fun things to do. I have always wanted to visit a cranberry bog – looks so interesting.

  6. Susan Whitehead

    Being from Florida, I’ve always been fascinated by the harvesting process of cranberries. Maybe one fall we’ll head up to MA to check it out.

    1. Leeanne

      I’m sure you and your family would enjoy visiting MA in the autumn.

  7. Eva

    Man, I love me some pumpkin fest, Oktoberfests, and the tv show Bewitched, so I really enjoyed your photos in this post. I’ve never been to Massachusetts but it’s been on my bucket list for a long time. One of these days…

    1. Leeanne

      Thanks, yes, the Bewitched statue is fun but the kids don’t know the show which makes it a little funny. I’m sure you would enjoy a visit to MA.

  8. kmf

    So many cool things to do! I’m planning to go to an apple orchard this weekend…and would love to visit that cranberry bog.

    1. Leeanne

      Yes, the cranberry bogs are fun to visit even when it’s not harvest time.

  9. Vessy Smith

    OMG! This is sooo beautiful! I miss real fall! Living in Texas, we don’t get to see all the amazing color changes, pick apples…and WOW, the cranberries…Loved your post! I want to visit Massachusetts during this time of year! 🙂

    1. Leeanne

      This time of year is special in Massachusetts for sure. We’d love for you to come and visit up here.

  10. Lisa Manderino

    I want to come to Massachusetts in the fall, I have only been during the summer. There is so much to do!

    1. Leeanne

      The summer is a good time for a visit as well. However, the leaves changing colors is pretty special.

  11. Shirley

    So fun! I love the cranberry harvesting pic!

    1. Leeanne

      Yes, it’s funny to see the garb you need to wear to harvest cranberries.

  12. Laura Speer

    What fun! I need to find something like that where I live. My grandkids would love it. Great pictures too!

    1. Leeanne

      I love to see these activities through the eyes of kids too.

  13. Wendy Robinson

    I have ALWAYS wanted to visit a civil war re-enactment. I don’t know why but it is something on my bucket list to see. I didn’t know they did that in Mass..

    1. Leeanne

      Yes, Old Sturbridge Village does it the reenactments. The one we went to was a weekend event at the beginning of August. I was really surprised by the whole event. All the different activities and demonstrations going on.

  14. Arianny Rodriguez

    I’m going to Massachusets in a few weeks! I must look into that Sleepy Hollow Experience, how cool.

    1. Leeanne

      Yes, the Sleepy Hollow experience will be very special. And the setting of Old Sturbridge Village will definitely heighten the whole show.

  15. Tricia Snow

    Looks like you make the most out of the season! Thank you for sharing!

    1. Leeanne

      Yes, my kids love to do all of these activities.

  16. Lori Nielsen

    I wish I would have had this guide when I was in Massachusetts in the fall a couple of years ago! We went apple picking, but there is so much more to do!

    1. Leeanne

      I think you can probably do a different activity each weekend and not repeat one for the whole season.

  17. jen

    yes please. The correct answer id D… all of the above!

  18. Missy

    We too would love to go apple picking! Finding our pumpkin will be a great adventure too.

    1. Leeanne

      It’s fun to see the kids picking their pumpkins. The way the check out the different pumpkins, roll them over and stand them up. Sometimes they have a specific idea in their heads that they need a certain shape pumpkin for. It’s all fun.

  19. Hera

    I’ve always wanted to check out Salem during Halloween season. That Apple looks perfect! I would enjoy Fall in Massachusetts with all these activities

    1. Leeanne

      Halloween in Salem is well over a month-long. However, the Grand Parade officially kicks off the holiday. But any time of year you can see people dressed up in Salem.

  20. Keagan

    The jousting looks awesome. I’d go just for that.

    1. Leeanne

      I agree the jousting is pretty awesome.

    1. Leeanne

      Jennifer, Renaissance fairs are really a lot of fun. Not only are there shows, activities and the outrageous food -turkey legs – but the craftsmen demonstrate everything from candle carving to jewelry making. I’ve bought some great treasures at these fairs.

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