Guest content and photo from Back Road Ramblers

Not only is Pittsfield, Massachusetts the largest city in Berkshire County, but its vibrant arts scene, whimsical restaurants, and abundant outdoor spaces make it the cultural and recreational heart of the Berkshires.

It’s also the perfect getaway for you and your dog. While Pittsfield is centrally located for exploring the entire region, there’s plenty to enjoy without ever leaving the city. Here’s a dog-friendly itinerary for three perfect hours in Pittsfield:

Let Loose at Burbank Park’s Dog Park

Has your pup been on their best behavior lately? Treat them to some off-leash fun at Pittsfield’s first dog park, located within Burbank Park. This shady, fenced-in space features two separate areas—one for small dogs and one for large. With plenty of trees, grassy space to romp, and benches for you to relax, it’s a welcoming spot for dogs to play and socialize.

Relax and Refuel with Your Pup

Just a short drive from the park, you’ll find plenty of spots to grab a bite or sip something refreshing—all with your furry friend in tow.

• Marketplace Café offers coffee drinks, sandwiches, salads, and more at its shaded sidewalk café—perfect for you and your pup to unwind.
• Patrick’s Pub features outdoor seating and a wide array of appetizers, soups, salads, sandwiches, burgers, and homestyle plates.
• Hot Harry’s Fresh Burritos is a casual Mexican-inspired spot with pet-friendly outdoor tables.
• Ben & Jerry’s lets you grab a cone and chill at their sidewalk tables with your four-legged friend.
• Looking to relax with a drink? Hot Plate Brewing has a dog-friendly taproom and outdoor seating where you can enjoy house-made craft beer, wine, hard cider, hard seltzers, and non-alcoholic options.

Explore Pittsfield State Forest

A visit to Pittsfield isn’t complete without a stop at the Pittsfield State Forest—an 11,000-acre expanse of wooded trails, quiet ponds, and mountaintop views. Pick up a to-go lunch from Marketplace Café and head out for some fresh air and forest adventure. (You’ll need to drive between trailheads, as the forest is vast.) Top trails and stops include: Shaker Mountain Trail: Starting at Hancock Shaker Village, this 2.6-mile out-and-back trail (or 6.5-mile loop) leads through serene forest and past the site of a historic Shaker settlement. It’s peaceful, not crowded, and a good moderate hike. Balance Rock: A short walk from the parking area brings you to a giant glacial boulder precariously balanced on a ledge for 13,000 years—and counting. It’s an easy, fascinating stop. Lulu Cascade to Berry Pond Loop: This scenic 5.2-mile hike features a bubbling brook, a small cascade, wildflowers, and sweeping views. Berry Pond Driving Loop: Short on time or energy? Drive the Berry Pond Circuit Road to the top, where you can picnic by the highest natural body of water in Massachusetts. 🗺️ Pro tip: Download a Pittsfield State Forest Trail Map before you go.

Other great hiking spots include Mahanna Cobble Reserve Trailhead (challenging trail), The Boulders (easy to moderate trails), Wild Acres Trailhead (easy).

Take A Step Back in Time

Leashed dogs are welcome on the grounds and inside the gift shop at the pet-friendly Herman Melville’s Arrowhead. Bring Fido and learn more about the famous author who penned “Moby-Dick.” Take a stroll along the Melville Trail to view the places that inspired his work. (Please note dogs are not permitted inside the historic home.)

Want Something A Bit More Paved?

If you and your pup prefer a smoother stroll, head to the Ashuwillticook Rail Trail, a scenic, paved path that begins in Pittsfield and winds north through the Berkshires. Once a former railroad corridor, the trail is now part of a nationwide network supported by Rails-to-Trails Conservancy. With flat terrain, water views, and plenty of fresh air, it’s a perfect leashed walk for both you and your dog.

Watch the Sunset at Onota Lake

End your dog-friendly adventure at Onota Lake, a 617-acre gem just minutes from downtown. Let your dog splash along the shore as the sun sets behind the Berkshire hills—a peaceful way to wrap up your perfect three hours in Pittsfield.

Shopping for the Pup

Forgot your pup’s food or just need to stock up on treats and toys? Benson’s Pet Center has you covered. This family-owned regional pet store carries a huge variety of dog food, beds, gear, and goodies. Even better, your purchases support Benson’s CARES, a mission-driven program focused on minimizing pet abandonment and helping homeless pets find loving homes.

A Room for You and Your Dog

Looking for a stylish stay that welcomes your four-legged companion? Hotel on North, a boutique gem in the heart of downtown Pittsfield, offers pet-friendly rooms for dogs of any size. For a fee of $45 per pet, per night, your pup can settle in comfortably by your side. Well-behaved pets may even be left unattended while you explore—just be sure to let the front desk know.

Need Help with Your Pup?

Whether you’re out exploring or away for the day, Love Us and Leave Us provides trusted, top-notch care for your dog. Founded in 2006 by Renee DeRagon, this premier daycare and boarding facility is known for its warm, attentive environment and unique free-range boarding—where dogs sleep in an apartment-style space with a staff member and fellow pups.

Whether you’re here for a quick visit or an extended stay, Pittsfield welcomes you and your pup with open arms. From scenic trails and lively dog parks to cozy patios and caring pet services, this vibrant city offers something special for every dog lover. So leash up, explore, and make memories together in the heart of the Berkshires.