The kids are back to school and there is a little chill in the air, which can mean only one thing: Autumn has arrived. While summer is glorious, the relaxed days and cozy weather of fall provide a perfect atmosphere for exploring the greater Boston area. Luckily, there are plenty of fall festivals in and around Boston that are full of fun for the whole family — as well as your favorite babysitter or nanny!
Whether you’re looking to go apple picking with the kids, taste some apple cider donuts, or celebrate Oktoberfest, these 10 fall festivals in Boston and the surrounding area shouldn’t be missed. So put on your plaid, zip up your boots, grab your pumpkin spice latte, and head out with the kids for an unforgettable autumn.
Smolak Farms Fall Festivals
Dates & Times: Saturdays & Sundays in September & October, 10 a.m. – 5 p.m.
Address: 315 S. Bradford St., North Andover, MA 01845
Phone: 978-682-6332
Fees: Kids, $12 | Adults & kids under 2, free | Corn maze & hayrides, $5
Smolak Farms in North Andover is a favorite destination for fun. It’s only about 40 minutes north of Boston and has everything your family wants in one stop. During the fall, Smolak Farms hosts festivals each weekend that include face painting, a bounce house, a train ride, and admission to the petting zoo and playground. Hayrides and a corn maze are also available for an additional $5 each.
Smolak Farms is great at producing family-focused fun, but behind the bounce houses and inflatable slides there is a charming New England farm that has been hosting families from greater Boston for generations. While you’re there, take time to pick apples or pumpkins, visit the geese by the pond, and stop by the farm stand for some delicious apple cider donuts.
Salem’s Haunted Happenings
Date & Times: Open daily through October | Check here for times.
Address: 265 Essex St., Salem, MA 01970
Phone: 978-744-3663
Fees: Free
Salem is arguably the Halloween capital of the world, so you will definitely want to visit this North Shore town during the month of October. The best thing about Haunted Happenings is that you can choose your own level of fright. If your little one just can’t wait until Halloween, check out the earliest trick-or-treating event around, happening October 6 in downtown. Wednesdays are family fun day throughout the month, with rides and other kid-friendly attractions on the Salem Common. For more information on family fun activities, click here.
It’s not all fun and games, however. There are also plenty of tours and informational events in Salem that aim to teach you the history of the town and its spooky past. Salem really is old, so if you’re bringing a stroller opt for one that can handle cobblestones and tight corners!
Topsfield Fair
Dates & Times: Sept. 29 – Oct. 9, Sunday – Thursday, 10 a.m. – 9 p.m. | Friday & Saturday, 10 a.m. – 10 p.m.
Address: 207 Boston St., Topsfield, MA 01983
Phone: 978-887-5000
Fees: Weekends & Holidays, $15 | Weekdays, $11 | Kids 8 & under, free with an adult | $9 prepaid tickets are available online.
The Topsfield Fair is one of the oldest agricultural fairs in the country, and after an amazing 199 years of operation the fair committee knows a thing or two about putting on an exceptional fall festival. The fair has something for everyone, from rides, games, and farm animals to shows featuring police dogs and monster trucks. And at just about 40 minutes north of Boston, it’s a great family destination.
Kids will love taking in all there is to see at the fair, and parents will love that admission for little ones is free. The fair is traditionally very busy, so be prepared to keep the kids close. Parking is usually a bit far from the entrance; you’ll have to walk a bit before you even get into the fair gates. This is definitely a fall festival that you’ll want to plan ahead for, but it is well worth the extra effort!
Douglas Octoberfest
Date & Times: Oct. 7, 9 a.m. – 4 p.m.
Address: Main Street, Douglas, MA 01516
Fees: Free
Sometimes you just feel like getting in the car and driving, and the destination is only part of the fun. If you’re feeling that way, head to Douglas Octoberfest. The town one hour outside Boston will give you all the charm of a small-town festival as well as a pretty ride.
Of course, the final destination is pretty great. Your kids will love watching the Weiner Dog Races (which happen at 9:30), jumping in the bounce houses, and listening to the great live music. If you’ve ever wondered that life would be like in small-town Massachusetts, this is your chance to find out and have a little fun along the way.
Cranberry Harvest Celebration
Dates & Times: Oct. 7 & 8, 10 a.m. – 4 p.m.
Address: 158 Tihonet Road, Wareham, MA 02571
Phone: 508-295-1000
Fees: Adults, $10 | Military & Seniors, $5 | Kids under 7, free
When you think of fall harvests you probably think of corn, apples, and pumpkins. However, there’s another great crop in Massachusetts: cranberries. Harvesting these berries is a completely unique process, which makes a trip to the Cranberry Harvest Celebration in Wareham a delight for adults and kids.
Parents will enjoy learning about the harvest and observing cooking demonstrations that will teach them how to integrate cranberries into all sorts of dishes. There is also the opportunity to wade into the cranberry bog and even take a helicopter ride over it. Kids will love the face painting, paddleboat rides, and pony rides available at the festival. If you can’t make the harvest weekend, be sure to check out the other tour dates for this cranberry bog an hour south of the city.
King Richard’s Faire
Dates & Times: Weekends through Oct. 22, 10:30 a.m. – 6 p.m.
Address: 235 Main St., Carver, MA 02330
Phone: 508-866-5391
Fees: Adults & kids 12+, $32 | Kids 4-11, $16 | Kids under 3, free | Admission at the faire is cash only. Tickets available online ahead of time for extra $2.
Take a step back in time when you bring the family to King Richard’s Faire, the New England Renaissance experience. At King Richard’s Faire you can experience what life was like in the Middle Ages, complete with lords and ladies, jousting, and bows and arrows. There are also acrobats and performers as well as rides. Of course, all of the nonstop activity can be a bit overwhelming, so this fall event is best for kids who don’t mind a little excitement.
On Saturday, October 14, at 4 p.m. kids under 12 can dress up as princes, princesses, and pirates for a kid-focused celebration as part of the Wee Ones Parade. They will even be able to get their picture taken with the king and queen. Any day of the faire young ones will love the Royal Zoo, where they can see extraordinary creatures such as tiger cubs and leopards.
Wellfleet OysterFest
Dates & Times: Oct. 14 & 15, 10 a.m. – 5 p.m.
Address: Main Street, Wellfleet, MA 02667
Phone: 508-349-3499
Fees: Admission, $10 | Kids under 12, free
Cape Cod is a long way to drive for a fall fest, but if you love seafood you won’t want to miss the Wellfleet OysterFest. Here you can learn all about the practice of shellfishing and, of course, taste some of the most delicious seafood possible. There are also plenty of other food and drink options and great live music.
Kids and parents will love the Family Fun Area. There you can find crafts, music, activities, and bounce houses that are perfect for little ones. Once the kids are tired out, check out the offerings of the fine arts and crafts vendors that come to OysterFest to sell their wares, and maybe even indulge in an adult beverage courtesy of several New England breweries and wineries.
Oktoberfest and HONK! Parade
Date & Time: Oct. 9, noon – 6 p.m.
Address: Harvard Square, Brattle Street, Cambridge, MA 02138
Phone: 617-491-3434
Fees: Free
Oktoberfest is one of the most beloved fall festivals, and Harvard Square’s event is a unique celebration that combines the classic festival with a distinctly Cambridge feel. Five beer gardens are spread throughout the square, and the streets are full of food offerings, crafts, and sidewalk sales.
The highlight of the event, especially for kids, is the HONK! Parade, which runs from Davis Square down Massachusetts Avenue to Harvard Square. The parade is full of big brass bands that aim to have the families of Boston dancing in the street. To get into the heart of the action, take the MBTA’s Red Line to Harvard Square, or opt for a spot along the parade route for a bit less of a crowd.
Opening Our Doors Fenway Festival
Date & Time: Oct. 9 (Columbus Day), 10 a.m. – 4 p.m.
Address: 337A Huntington Ave., Boston, MA 02115
Phone: 617-437-7544
Fees: Free
This year on Columbus Day the Fenway Alliance hosts “Opening Our Doors,” an event that invites the public to free art, history, music, and cultural events throughout the Fenway Cultural District. There are plenty of events to choose from. Kids will love the Paint & Play Piano at the Christian Science Plaza. There will also be performances by the Boston Children’s Chorus and other groups.
If your child is little enough to be carried or old enough to behave reliably, you’ll also enjoy the Gallery Walk, during which art galleries throughout the Fenway area open their doors to visitors. If you’re dealing with more-lively little ones, you can set up shop on Christian Science Plaza, where various entertainment offerings will take place all day.
Ipswich Chowderfest
Date & Time: Oct. 15, 11 a.m. – 4 p.m.
Address: 130 High St., Ipswich, MA 01938
Phone: 978-356-9055
Fees: Admission, $10 | Kids under 10, free
If you’re from Boston chances are you love clam chowder, so why not go try some of the best chowder in the state at the Ipswich Chowderfest? The food will delight Mom and Dad, with chowder from 10 area restaurants. Ipswich Ale will also be a vendor at the event. In addition, there will be kids activities and crafters.
We suggest visiting the Chowderfest and then making a day out of your visit to Cape Ann. Not only is the area gorgeous during the fall, but there are also plenty of family-friendly activities, like apple picking and corn mazes. Let the kids get tired and then enjoy a drive around this rural seacoast area while they sleep!
What’s your favorite fall festival around Boston? Let us know in the comments below!
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