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Rediscovering The Berkshire’s Dog-Friendly Spots

Posted on October 13, 2020Written by Mike Powell
Updated on April 14, 2022

dog friendly

Life is getting back to normal, and if you and your pooch are looking for an outing to take together, here are some of the Berkshires’ best dog-friendly spots.

By Mike Powell

The Berkshires is one of the most dog-friendly areas around, but if you’ve been stuck at home with your pup lately you may need a quick refresher on the best pup-human date spots.

If you’re due for some bonding time with your pooch, why not spend a day checking out the pup-friendly attractions?


Hilltop Orchards

Tire your pup out with the walk of a lifetime around the Hilltop Orchards. For an easy trail, walk up to the top of the Hilltop Orchard, where the two of you can take a rest and look out over the Berkshire hills. For dogs with more stamina, there’s a trail through the woods of about 2.2 miles.

Ashuwillticook Rail Trail

Whether you prefer walking, biking, or rollerblading, this 12.7-mile route will suit you and your dog. The trail follows an old railroad track, and meanders through 3 towns with some interesting landmarks and stunning scenery along the way.

Arcadian Shop

Outdoor enthusiasts (and their pups) will be right at home in this sporty shop. While entrance is limited to a few at a time currently, they’ll warmly welcome both you and your pooch for a chat and a browse. You can also walk and hike the dog-friendly trails of Kennedy Park, which is accessed from the shop’s parking lot.

Eat At…

The ’6 House Pub

This eatery has been serving guests since 1948, and have many celebrities on their list of happy customers. When you’re there, though, you and your dog will feel like the guests of honor, with a superb menu and a special Bone Appetit Menu for the fluffs. Even picky eater pups will love it!

No. Six Depot

For a quick stop coffee and bagel, this is the place for you and your pooch. Make sure to sit at a dog-friendly table and the staff will treat you and your fluff to a fantastic experience.


This little gem makes fresh, tasty food from 8 – 10am and from noon onwards on weekends. Whether you and your pup are in the mood for a granola breakfast or a chunky burger, stop by here and grab something while it’s hot!

Bright Ideas Brewing

Right across the way from A-OK is Bright Ideas Brewing. When you need some hydration after a long hard day out with your pup, stop by here for a cool refresher. Your dog is welcome to chill with you on the patio as long as they’re relaxed and kept on-leash to be safe.

Stay At…

The Red Lion Inn

The Red Lion Inn loves fluffs of all descriptions, and lets yours stay with you for $40 per night. Call ahead to make sure, and don’t forget to bring chew toys and treats to keep your pooch entertained!

The Williams Inn

The Williams Inn is a sleek, luxurious lodge, within close distance of plenty of cultural gems for you and your fluff to visit between resting in one of their pet-friendly rooms.

The Briarcliff Motel

It’s apparent on entering that the Briarcliff is a pet-loving place. Dog cushions, a “Dogs of Briarcliff” photo wall, and their own furry feline ambassadors speak to their love of animals. For $20 a night, your fluff can share your room. Be sure to take them out on the leash regularly for potty breaks.

Hotel on North

This eccentric boutique hotel is worth a visit if you and your pooch are looking for an overnighter. It’s packed with vibrant personality, sprinkled with artwork, and pet-friendly. They encourage you to bring your pup along, and reserve rooms for guests with pets.

The Porches Inn

The Porches Inn allows up to 2 pets at $25 per night. There’s a dog park next to the hotel if your pup has energy to burn, and pet bowls and waste bags are provided upon request.


There’s no need to leave your pup at home when you want to get out and about in the Berkshires! Now is the perfect time to catch up on what you’ve both missed over the past few months and rediscover some of the Berkshires’ dog and human-friendly spots.

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