5 Outdoor Areas to Bring Your Pet in Great Barrington

If you’re anything like us, your dog goes everywhere with you—and at Little Lion Inn, we wouldn’t have it any other way. The Berkshires are incredibly pet-friendly, especially in the warmer months, with plenty of places to explore side by side. Now that you’ve found the perfect place to stay with your pup, here are some of our favorite dog-friendly outdoor spots in and around Great Barrington.

1. Dine: Barrington Brewery & Restaurant

A local favorite for casual dining, Barrington Brewery offers a relaxed outdoor patio where dogs are typically welcome during the warmer months (it’s always a good idea to call ahead to confirm).

Pair house-brewed craft beer with classic pub fare while your pup lounges by your side. With a focus on sustainability—including solar-powered brewing—it’s a feel-good stop for both you and your dog.

2. Hike: Monument Mountain (Hickey & Peeskawso Trails)

One of the most iconic hikes in the Berkshires, Monument Mountain is a great option for active dogs and their humans. The popular Hickey and Peeskawso trail loop is about 3 miles, offering forested paths and rewarding summit views.

Note: Dogs are allowed but must be leashed, and some sections are moderately steep—best suited for dogs comfortable on uneven terrain.

3. Walk: Flag Rock Trail

For a shorter but still scenic outing, Flag Rock is a local favorite just outside downtown. This roughly 1.5–2 mile out-and-back trail leads to a rocky overlook with views of Great Barrington and the Taconic Range.

It’s a great option for a quick hike with your pup—moderate effort, big reward.

4. Explore: Lake Mansfield

Lake Mansfield is one of the best all-around outdoor spaces in town. With walking trails, wooded areas, and open green space, it’s perfect for a relaxed day with your dog.

Important: Dogs are welcome on trails (leashed), but are not permitted on the public beach/swimming area—something to keep in mind during summer visits.

5. Stroll: Downtown Great Barrington

Sometimes the best activity is simply wandering. Great Barrington’s walkable downtown is incredibly dog-friendly, with many shops putting out water bowls and welcoming well-behaved, leashed dogs inside.

Pop into spots like The Bookloft (policies can vary, so check at the door), grab a coffee, and enjoy a laid-back afternoon exploring together.

Stay at Little Lion Inn

After a full day of exploring, hiking, and relaxing with your pup, head back to Little Lion Inn—your home base in the Berkshires.

We’re proudly pet-encouraging (with no pet fees), so your dog is just as welcome as you are. With easy access to trails, parks, and downtown Great Barrington, it’s the perfect place to stay for a dog-friendly getaway.

Book your stay and bring your best friend along for the adventure.