Planning a Dog-Friendly Trip to the Berkshires

History, fall colors, dog-friendly hotels, and some really great food.

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Is it crazy that for most of the year I forget how much I love fall?

From December through August, I’d tell you that my favorite time of year is either summer (I’m freezing the other nine months) or Christmas (hello, twinkle lights, my birthday, and cookies galore).

But then that crisp September air arrives, and I remember all over again how much I love fall.

Having grown up in Seattle, the changing weather always makes me want to get out into nature—to smell some woodsmoke, pick some pumpkins, and do some hiking. This year, I was craving a trip out of the city so much that (on a whim!) I booked a trip to the Berkshires. Josh and I have happy “pre-dog” memories of getaways to the Berkshires, and I had been dreaming of going back. Plus, there are a ton of unique, dog-friendly hotels!

We stayed in Stockbridge’s famous Red Lion Inn, which is one of the oldest hotels in the U.S. (established 1773!) and spent a blissful weekend enjoying the fall colors with the pups.

Scroll down for our pictures and our recommendations from our trip.👇🏻

 Fall colors at Mount Greylock

Fall colors at Mount Greylock

 Dog-friendly drinking at The Red Lion

Dog-friendly drinking at The Red Lion

Planning a Dog Friendly Trip to The Berkshires on The Dapple Dog Lifestyle Blog | The Red Lion Inn
Planning a Dog Friendly Trip to The Berkshires on The Dapple Dog Lifestyle Blog | The Red Lion Inn
Planning a Dog Friendly Trip to The Berkshires on The Dapple Dog Lifestyle Blog | The Red Lion Inn
 Giant pumpkins outside The Red Lion Inn

Giant pumpkins outside The Red Lion Inn

 Downtown Stockbridge

Downtown Stockbridge

 Dave loved our in-room fireplace at The Red Lion Inn

Dave loved our in-room fireplace at The Red Lion Inn

Planning a Dog Friendly Trip to The Berkshires on The Dapple Dog Lifestyle Blog | The Red Lion Inn
Planning a Dog Friendly Trip to The Berkshires on The Dapple Dog Lifestyle Blog | The Red Lion Inn
Planning a Dog Friendly Trip to The Berkshires on The Dapple Dog Lifestyle Blog | The Red Lion Inn
 The view from Mount Greylock

The view from Mount Greylock

Planning a Dog Friendly Trip to The Berkshires on The Dapple Dog Lifestyle Blog | The Red Lion Inn
Planning a Dog Friendly Trip to The Berkshires on The Dapple Dog Lifestyle Blog | The Red Lion Inn
Planning a Dog Friendly Trip to The Berkshires on The Dapple Dog Lifestyle Blog | The Red Lion Inn
Planning a Dog Friendly Trip to The Berkshires on The Dapple Dog Lifestyle Blog | The Red Lion Inn
Planning a Dog Friendly Trip to The Berkshires on The Dapple Dog Lifestyle Blog | The Red Lion Inn

Do:

Mount Greylock: Load your pups in the car and drive up to Mount Greylock, the highest point in Massachusetts. From the top, you’re rumored to be able to see for 90 miles on a clear day. Dogs must be leashed, but there are some great (and easy) hiking trails too.

The Melville Trail: Take The Melville Trail at Monument Mountain to hike where Nathaniel Hawthorne, Herman Melville, and Oliver Wendell Holmes famously took shelter in a cave during a thunder storm… and ended up hashing out the idea for Moby Dick.

The Norman Rockwell Museum: No trip to Stockbridge is complete without a trip to The Norman Rockwell Museum, even though they sadly don’t allow dogs on the gorgeous grounds. Did you know that Rockwell famously said that if a painting wasn’t working he could always fix it by adding a dog? Our kind of guy.

Downtown Stockbridge: We’re obsessed with downtown Stockbridge’s picturesque streets (especially in fall!) and unique shops. Leash up your pup and take a stroll through the downtown area with some coffee from Barrington Coffee Roasting Company. We also love picking up a fall candle (or ten!) at the tiny downtown Yankee Candle Store.

Museum of Dog: It was closed when we visited, but we’re dying to go back and visit the Museum of Dog.

Eat and Drink: 

No. 6 Depot Coffee and Roastery: Don’t miss this amazing roastery that’s located in the oldest train station in the Berkshires. The best part is that their patio’s a perfect spot to hang out with a pup.

The Courtyard at The Red Lion Inn: We loved our stay at The Red Lion, but we were especially grateful for the outdoor dining areas (weather allowing) where we could get a snack or a drink with our dogs.

Chocolate Everything: Swing by Peace, Love, & Chocolate for a sweet fix. If you’re lucky, you can get a seat outside.

Stay:

The Red Lion Inn: We love the historic grounds and antique-filled rooms at The Red Lion Inn. Pets are welcome in some guestrooms. The cost is $40 per night, per pet. You’ll have to call to book, but you can also find more details about the pet policy here.

Hotel on North: We’ve stayed at Hotel on North in the past (a sister inn of The Red Lion) and are huge fans of its cozy, mid-century aesthetic and fabulous restaurant. (Led by a former White House chef!) Pet stays are $40 per night, per pet. More details can be found here.

Porches: We’re dying to plan a trip to this chic boutique hotel in North Adams. They welcome pets for $25 per night, per pet. More details can be found here.

Have you visited the Berkshires with a dog? Tell us what we missed in the comments!