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Lookout Farm Apple Picking

A day of fall family fun

By Katy Cirrone, Wakefield Macaroni Kid Publisher October 14, 2023

Apple picking is one of those things every New England family checks off the bucket list in late-September or early-October. Living in the Boston area, there are lots of orchards to choose from, each seeming to offer more and more for each year.

For the past two years, we have visited Lookout Farm in Natick. This family-owned farm is massive, complete with apple and pumpkin picking, an outdoor restaurant, a corn maze, kids play area, and more. 

It seems to get increasingly popular each year, so here are my tips for visiting Lookout Farm:

  • Get there early! It opens at 10 a.m. and when  we arrived at 10:15 a.m. on Sunday, October 8, the lot was already filling up.
  • Get tickets in advance online. This allows you to cut the long line to enter. Kids under 2 are free, but other than that, be prepared to purchase a bag per person.
  • Have the kids wear rain boots or footwear you don’t mind getting dirty. With all the rain we’ve gotten, some areas were a bit muddy.
  • Bring an all-terrain stroller or wagon. If you have little ones, a Thule/Bob stroller or wagon like a Veer is a good idea. Having some way to transport your kids is smart because you can put your apples in there as you go along. You can always keep it on the pathways as you pick apples.
  • Have a beer and let the kids play in the Beehive Beer & Cider Garden. I don’t remember seeing this last year and it was a great surprise at the end of apple picking. There are tons of things for kids to do - live music, playground, a bounce pad, ride, animals, and more. There are beer stands and picnic tables set up as well.
  • Pick up pumpkins, beers, and other treats on the way out. There’s a pumpkin patch near the parking lot and a stand with goodies to go next to the outdoor restaurant. If lines are long, you can also stop at the store, which is right before you pull in/out of the Lookout Farm entry point in your car.