Being Berkshire County’s biggest city and county seat means that pupperific Pittsfield has so much to offer you and your barking bestie. This bustling city is packed with veterinary clinics to ensure your pooch is in tip-top shape for all the wagging wonder that awaits you here, and there are endless pawssibilities for adventure in the numerous dog-friendly parks and restaurants dotted around the city. Pittsfield has the best of a fast-paced, thriving city with a welcoming populace, and it ensures you never feel starved for nature by combining rural and urban with many wondrous wooded parks.
Springside Park is Pittsfield’s largest park and is a marvelous meadowed oasis in the city. There are paved paths for you and Fido to stroll along and rolling hills, ponds, and streams to admire. The park also grants access to the Ashuwillticook Rail Trail, which features a path enfolded by wildflowers on either side and is good for all skill levels. Pittsfield State Forest covers 11,000 acres and has whimsical waterfalls, whirlpools, and more in the midst of its forested majesty. This park has many looped trails pawfect for some leashed laps. Dottie’s Coffee Lounge and Ayelada are just two of many restaurants in Pittsfield waiting to welcome you and your darling dog in their outdoor seating areas.
If you’ve got a companionable canine who loves to chat and you’re looking for some off-leash oppawtunities for socializing, then French Park Dog Park in North Egremont is the place to be! Set on a hilltop and surrounded by trees and mountain views, this is a great open space to run, sniff, and play. There are benches for owners to sit and mingle, as well as some shade for those scorching summer days. Doggy waste bags are provided, but be sure to bring water to keep Fido hydrated while he makes the most of this splendid space. There is no separate area for small dogs, so ensure your hound is happy playing with dogs of all shape and sizes.
The lovely town of Lee is home to part of October Mountain State Forest, which is the largest state forest in Massachusetts and an "appaws"-worthy spot for walkies. Fantastic forest trails can be found throughout the forest as you traipse through the trees, and dogs are welcome to go off-leash on these treks, but they must remain leashed in other parts of the forest. There’s a 2.7-mile interpretive trail around the Washington Mountain Marsh, a route through the gorgeous Schermerhorn Gorge, and access to the Appalachian National Scenic Trail, which is one of the longest hiking-only trails in the world.
Hopkins Memorial Forest is a 2,600-acre nature reserve that contains close to 15 miles of walking trails for you and your four-legged favorite to explore. This mighty forest spans across the corner of Massachusetts, New York, and Vermont but its trailhead is located in Williamstown. The two loop trails give you and Sparky about 4 miles to roam through the picturesque woodlands, and there are many things to "paws" and admire along the way, like Maple Sugar Shacks and the Moon Barn. The Stone Hill Hiking Trail is one of the most pawpular places to walk in Williamstown as it offers a breathtaking panoramic view of the whole town and has moderate trails suitable for even the sleepiest couch puptato!
Are you and your fittest furry friend hoping to climb mountains together and catch some mutts-see views? Then Mount Greylock State Reservation is a doggone good place to start. The incredible trails can take you and your leashed dog to the highest point in Massachusetts for unforgettable vistas of up to 90 miles in the distance. Don’t forget to snap a fetching photo of your pup when they reach the top! If your puppy doesn’t want to take on the summit, there are numerous walking trails that range from easy to strenuous. You’ll definitely need something to sink your teeth into after that, so why not head to Arizona Pizza for a slice or a slurp in their dog-friendly outdoor picnic area?
There’s no bones about it -- Great Barrington has one of the best places to bring your precious pooch in the state of Massachusetts. Monument Mountain Reservation is a 503-acre open space that is renowned for its out-of-this-world views of Housatonic River Valley, the Taconic Mountains, the Berkshires, and the Catskill Mountains of New York. The site has inspired many writers throughout the years, and when you behold its beauty, you will understand why. Hickey Trail features a wonderful waterfall and is just one of many tremendous trails and walking paths to be found here. Pop a leash on Lassie and enjoy exploring this enchanting spot.