
Planning a trip to the apple orchard this fall? One of my favorite fall New England traditions is apple picking, and I hate to have to leave my dog behind. After all, apple picking is way more fun when you can do it with your pup! Here are a few of my “picks” for the best dog friendly apple orchards in New England, all within a two hour drive from Boston.
Red Apple Farm, Phillipston, MA
Red Apple Farm is a fourth generation family farm located in Phillipston, MA, about an hour and half drive from Boston. There’s so much to see, taste, and do at this quintessential New England farm that’s fun for the whole family – including four-legged members! Apple picking is of course the main reason to visit – and dogs are allowed on leash in the orchard. There are also pumpkins, flowers, and a variety of rotating PYO crops.
Kids will love the petting zoo on site, in addition to free-roaming hens and roosters, but take extra caution if your dog is reactive around other animals. Once you’ve worked up an appetite, visit the food trucks or grab a picnic table outside the Brew Barn where you can sip a sampling of beers and ciders on tap. And before you leave, stop by the country store to stock up on farm-fresh treats like fresh apple cider donuts served right out of the fryer. Check their website for seasonal events, like weekend BBQs and live music lineups.




Drew Farm, Westford, MA
Located just 45 minutes from Boston, Drew Farm is one of the most family and dog friendly orchards I’ve ever visited. This hidden gem is perched on a beautiful hill with stunning views of the surrounding fall foliage. You won’t find not a lot of fancy extras (and therefore not a lot of crowds either), but you will find everything you need for a perfect family fall outing. There is a fire pit for toasting marshmallows, plenty of picnic tables, and live music on the weekends. Be sure to pack a picnic, as there’s no food served on site – other than cider donuts and s’mores! The staff was so welcoming, offering treats and candy to both our kids and Roscoe. Halloween is an extra special day at Drew Farm, when the orchard paths are lined with hundreds of lit Jack o’ Lanterns.



Doe Orchards, Harvard, MA
Doe Orchards located in Harvard, Massachusetts just within an hour’s drive from Boston, is another one of my favorite, under-the-radar apple orchards that allows dogs. Even during peak times, we found the place relatively quiet and crowd-free. You won’t find a lot of the extra bells and whistles of other apple picking places (look elsewhere if you’re only in it for the apple cider donuts, wagon rides, or corn mazes). But that’s exactly its charm. It’s simply about being out in nature, and the surrounding foliage is so pretty and peaceful. They also have a Christmas tree farm if you want to come back in the winter!




Hollis Hill Farm, Fitchburg, MA
Hollis Hill Farm is family owned and operated farm set atop a hillside in Fitchburg, about an hour west of Boston. Here you can pick your own apples, pumpkins, and even flowers. Afterwards, enjoy food and drink at the large lawn area with picnic tables and live music. Dogs are allowed on the lawn and all outdoor areas. The retail store sells sweets like ice cream and hot, fresh cider donuts that sell out within minutes of being made.


Nashoba Valley Winery, Bolton, MA
Nashoba Valley Winery, an hour outside of Boston in western Massachusetts, offers fun for the whole family. The beautiful grounds boast a winery, brewery, distillery, and a restaurant. Kids and dogs will love wandering the apple orchard and vineyards, and you’ll love relaxing with a glass of wine and a cheese board afterward.

Tips for Apple Picking with your Dog
Apple picking is a fall activity that’s fun for the whole family – including your dog! Below are some tips to make your trip fun for everyone:
- Apples are safe for dogs to consume and make for a tasty treat! Just watch out for rotten or insect-infested ones on the ground.
- Be respectful. Bring poop bags with you and clean up after your pup, and keep your dog on leash and in control around others, especially kids.
- Keep your distance from other animals. Only approach other dogs with their owners’ permission, and stay clear of farm animals. We learned on a previous trip that our dog wouldn’t stop barking at horses (he is a shepherd after all), and he nearly caused a stampede.
- Always call ahead to make sure the orchard is okay with you bringing your dog. Information on the web could be outdated, and you don’t want to find out their rules have changed after driving all the way out to the country.
- Have fun! Explore the trails, take lots of pictures, and enjoy a beautiful, fall day at the orchard with your best friend.




Do you know of other dog-friendly places to go apple picking in New England? Share in the comments below!

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