With the cooler temperatures and the majority of people back in a regular routine or back to school, it’s the perfect time to explore Boston as a family whether you’re visiting or local.
Originally published in 2016, this has been updated for the 2018 calendar, see what your family can enjoy this year!
This Boston Fall Family Travel guide has some great ideas to mark off your list in October or November. PLUS, if you’re looking to go somewhere else in the US, check out the bottom of the post for other fall travel guide perfect for families.
Go on the Freedom Trail!
It doesn’t matter if you have done it 5 times or never, enjoy a day or two exploring the Freedom Trail. With most of the tourists gone, this is a great time to explore and enjoy it… especially with cooler weather as well. And if you don’t have a lot of time, can’t walk that uch, or find it interesting, take the hop-on, hop-off Freedom Trail Trolley.
Take a self-guided walking tour of Beacon Hill
Beacon Hill is always beautiful, but the cooler temperatures seem to make it extra nostalgic. This walking tour linked about starts at the State House and takes you to Liberty hotel. Take it at your own pace, stopping in the shops and grabbing a bite to eat along the way.
Go apple picking
It’s truly a New England thing to do. And not only do you get quality time together with friends and family, it’s a beautiful day trip to visit a picturesque apple farm with all the fall foliage. We personally love Cider Hill. They have great orchards, a fabulous store (that’s already stocked with a few holiday treats), you can watch them make cider donuts, and they have food and drink available. They also have animals, swings, oversized tricycles, a picnic area, hay to jump on, and more.
Another family favorite is Lookout Farm! They have a ton of extra activities for kids, a train, and more.
Be a spectator at the Head of the Charles’ Regatta (October 20-21)
Find an event location for the regatta and enjoy the fan fare and fun! And if you have never been to an event like it before, learn basic regatta information and make it a fun learning experience for the whole family. And to be able to see the rowing happening on the beautiful Charles River in the fall is a picturesque sight! And since it’s within walking distance of the city, you can make an easy day of exploring Boston… like that Beacon Hill walking tour perhaps?
Attend the Boston Book Festival (October 13)
This is a free family friendly event in Boston this fall, but is suitable for all ages. To enjoy all of the exhibits with your kids, they can participate by getting stamps on their Passport to Imagination to have the opportunity to win a prize! Download a schedule here or follow latest news on their facebook page.
Visit Plymouth for Thanksgiving
Enjoy time together while learning and celebrating one of America’s most beloved holidays, thanksgiving. Check out the event list for the 3 day festival that includes everything from a parade to demonstrations and even a concert.
Visit Christopher Columbus Park Trellis Lighting event (End of November)
Especially if you love Christmas lights, gear up for colder weather and the magical holiday season by planning a visit to see the lighting of the trellis and you enjoy music and snacks as a family.
What a great resource for families in the area Kara! The book festival sounds like so much fun. I wish we were closer so we could go!!
We wanted to go to that one, but were busy this weekend. I am hoping to catch it in the coming years!