pumpkin patch

Who doesn’t love fall in Boston?! With the cooler temperatures, cozy sweaters, beautiful leaves, and a variety of autumn adventures in store, Boston is at its best each autumn! Whatever you’re in the mood for, we’ve got you covered with a list of 20 things to do in and around Boston this fall!

1. Go leaf peeping

You could adventure all over New England to view the fall foliage, but some of the best spots are right here in our own Boston backyard. I love visiting Boston Common, the Public Garden, and the Arnold Arboretum every autumn for my leaf-peeping fix.

2. Take a hayride

Many farms near Boston run hayrides each fall — some spooky and some tame. Smolak Farms’ hayride is a great one, and it runs every weekend in September and October.

3. Spend a day at a classic fall fair

The Topsfield Fair is your classic fall fair — with all the fair food, petting farms, rides, entertainment, pig races, and contests you can handle! Kicking off September 29 and wrapping up October 9, this fair is a popular one, so grab your tickets ahead of time and avoid the long lines.

4. Go apple picking

Is it really fall without apple picking? Orchards all over New England open up their farms every fall for all sorts of fall activities in addition to apple picking, like petting zoos, pedal carts, pumpkin bowling, bounce houses, and more!

5. Bike along the Charles River

Fall is the perfect time to bike the Esplanade! Check out this handy clickable map, then make stops at the many playgrounds, art installations, gardens, and historical sites as you bike around.

6. Get lost in a corn maze

Test your navigation skills at one of the many corn mazes near Boston! There’s a “mega maze” at Davis Farmland and excellent mazes at Connors Farm and Honey Pot Hill Orchards.

7. Get spooked in Salem

There’s nothing like Salem in October. There are historic sites, museums, quirky shops, and “Hocus Pocus” landmarks. Then there’s the legendary Salem Haunted Happenings, a festival throughout October with events for the whole family, including a parade. Be prepared for massive crowds and tricky parking, though!

8. Visit a pumpkin patch

Many of the farms that offer apple picking also have pumpkin patches. Tyngsboro’s Parlee Farms grows more than 13 acres of pumpkins!

9. Watch the Head of the Charles Regatta

From October 20-22, stand at the edge of the Charles River and watch the world’s largest three-day rowing competition — there will be 11,000 participants this year!

10. Check out New England’s biggest fall fair

It’s New England’s biggest fall fair, and The Big E has tons of entertainment, food, animals, and rides from September 12 to October 1.

11. Say “boo” at the zoo

The Stone Zoo hosts this event every fall with a trick-or-treat trail, costume contest, and animal encounters. This year’s event is on October 22 and 23.

12. Get thyself to King Richard’s Faire

New England’s Renaissance festival — King Richard’s Fair — is entertaining for the whole family. There’s entertainment, rides, games, and signature food and drinks from September 2 through October 22.

13. Explore the Boston Common

This city gem is so easy to take for granted. But it’s a true treasure for area families — all 50 acres of it! Pause for a picnic in America’s oldest public park, and take in the colors of the changing leaves. Enjoy the many sculptures and memorials, and let the littles run free in the fields or at the playground!

14. Take a hike

What’s prettier than a hike with views of fall foliage? Best part is, you don’t have to go too far from home! These 10 family-friendly trails are all within two hours of Boston.

15. Stroll the Greenway

The Rose Kennedy Greenway covers 1.5 miles of park area that curves through Boston. The park is beautifully landscaped, with food trucks, a beer garden, and art exhibits along the way.

16. Go sky-high for the best views of Boston

View Boston is a new 360-degree observation deck on the 52nd floor of the Prudential Tower. It offers breathtaking panoramic views no matter where you stand — what a way to view Boston’s changing fall leaves! Plus, there’s a restaurant and bar up there, too.

17. Pick up fresh apple cider donuts

You’ll find apple cider donuts at many New England apple orchards, but you can get this local delicacy at many Boston-area bakeries, too! Wilson Farm, Kane’s Donuts, and Pizzi Farm all have delectable offerings, but my favorite is at Union Square Donuts! In addition to this cinnamon and clove sugar-dusted deliciousness, they have other seasonal donuts, including maple creemee, candied apple, and pumpkin spice latte.

18. Catch a football game at Harvard Stadium

If the thought of heading to Gillette with your family is daunting, consider catching a local Harvard football game right in Allston! Harvard Stadium is America’s first and oldest intercollegiate concrete stadium. Youth tickets go as low as $5 for some games, and there are lots of other promotions to make these games accessible to all!

19. Enjoy the spooky festivities at Six Flags

Take a ride out to Agawam and experience spooky fun for all ages at Six Flags Boo Fest from September 16 to October 29. There’s trick or treating, family-friendly rides, lawn games, pumpkin decorating, crafts, and more. Or, for the real thrill seekers, try the Fright Fest, with haunted houses, scare zones, and rides in the dark from September 23 to November 5.

20. Soak up local history in Plymouth

Fall is the perfect time to explore this outdoor interactive museum in Plymouth. You can get a feel for what life was like in a 17th-century English village, then visit historic Patuxetalong along the Eel River to learn about the Native peoples who have lived there for over 12,000 years.

Ranessa Doucet
Ranessa is a Boston native who grew up in Charlestown and never gets tired of exploring the city. She now lives north of Boston with her husband, two kids, and two mischievous pugs. Ranessa earned her master’s degree in elementary education and licensure in early childhood education. She currently works as an Academic Interventionist and Freelance Writer. Ranessa loves writing about parenting tweens, exploring New England, health, and self-care. When not writing or reading, you can find her watching reality TV, eating chocolate, attending her kids’ sporting events, and dreaming about the beach.