Bark-cation Adventures in the Berkshires of Western Massachusetts
- Luie Boone
- Oct 3, 2025
- 11 min read
This travel spot is featured in our fourth blog series, Hounds Honored.
Luie Boone thought he overheard his hoomans talking about a vacation to the Barkshires of Western Massachusetts. What his hoomans actually said was a vacation to the Berkshires of Western Massachusetts, which Luie Boone probably would've heard the first time around, if he wasn't so busy sniffing out snacks and stealing treats behind his hoomans' backs. You can't blame him, though; that pooch loves his food. Even though there's no bark in its name, Luie Boone couldn't be more excited to take a trip to the Berkshires. He learned that it was named after one of America's Last Great Places by The Natural Conservancy (TNC), and then he started wondering why.
It turns out Berkshire County is one of the most ecologically rich regions in Massachusetts, being home to over 150 rare or endangered species. Its unique wetland plant communities and expansive forests support wildlife like black bears, bobcats (Luie Boone wonders if bobcats are as scary as his kitty brother, Tobi), and migratory birds. The county's woodlands form a vital corridor linking northern forests with the Appalachian range, making it a key habitat for roaming species. Only Cape Cod surpasses it in the number of protected species. This is why its largely unbroken forests—which stretch into New York and Connecticut—have earned the area national recognition for its biodiversity and conservation value!
Luie Boone thinks a vacation with his hoomans in the Berkshires of Western Massachusetts would be a paw-some way to enjoy scenic beauty, outdoor adventures, and small-town charm. With rolling hills, forested trails, and dog-friendly amenities, the region makes it easy to include your pooch in every part of the journey. But where should your journey in the Berkshires start? Don't stress, Luie Boone will give you a couple places to check out during your vacation.
Pittsfield is a great starting point. It has the largest population in Berkshire County, and it serves as its county seat! Incorporated in 1761, the city was named by Royal Govenor Sir Francis Bernard (Luie Boone reckons that's a Saint Bernard and not a hooman; his hoomans tell him he is wrong). Governor Sir Francis Bernard named Pittsfield after British politician William Pitt. Did you know that William Pitt served as the Prime Minister of Great Britian from 1766 to 1768? Luie Boone did not.
Did you know that Pittsfield has a bunch of cool places to check out? Luie Boone did, and he's going to tell you about those local gems now. There's Burbank Park on Lake Onota, and the Friends of Pittsfield Dog Park. There's also the Ashuwillticook Rail Trail, which is an old railroad track that was converted into a 12.7-mile paved trail. If you're looking for a place to swim, boat, or fish, Laurel Lake is the place for you. Laurel Lake is over 165 acres surrounded by forests and roll hills. Unfortunately, the lake has faced environmental challenges, including acidification, invasive species (like water chestnuts!), and algae blooms! Please be wary of algae blooms, as they can be deadly if dogs ingest its toxins. Instead of ingesting toxins, bring your dog to Dottie's Coffee Lounge! This restaurant not only welcomes dogs, but it also has a special dog dinner night—including a carrot and apple salad; plain chicken thighs, steamed beats, and brown rice for the main course; and a peanut butter yogurt parfait with blueberries, bananas, and dog biscuit granola for dessert!
The town of Great Barrington is a must-visit for its outdoor fun and unique culture. His hooman sister, Rachel, would be thrilled to know it is home to the Ski Butternut resort, which is a ski resort with 22 trails! Luie Boone knows he can't tag along on a ski trip, but he'd be fine hanging out with his paw-rents while his sister takes the slope. They can check out Monument Mountain and its 2.5-mile-long quartzite ridgeline. Or they can head over to Lake Mansfield Park, which has a beach area, small pond, lakeside trail, and forest system! Afterwards. the whole family can meet up at the Prairie Whale Brewing Company on their pet-friendly patio to get some farm-to-table food.
Lennox is another wonderful town to visit, with its natural beauty and cultural highlights. It is the site of the Shakespeare & Company (a professional live theater), Tanglewood (a renowned outdoor music festival), and the Boston Symphony Orchestra (a 1900 concert hall)! Although dogs are not allowed on the grounds, there are trails and parks nearby that they can enjoy—such as the Kennedy Park, which has gorgeous views from the summit. Dogs are also allowed on the grounds of the historic Edith Wharton Home: The Mount. In fact, Edith, a famous novelist loved dogs. She had a terrier, poodles, and two long-haired Chihuahuas! Luie Boone hopes he can learn some history about those pooches while there. The Norman Rockwell Museum welcomes dogs in the outdoor area and even hosts a Community Dog Day. Like Edith, Normal Rockwell loved dogs! He owned a collie, and dogs were a reoccurring theme in his work—as such, you can see dog-themed art inside of the museum.
Be sure to also visit the town of Williamstown, which shares a boarder with Vermont to the north and New York to the west. The Mount Greylock State Reservation is a must-visit here. Dogs should be leashed at all times on the reservation, in order to help protect and respect the local wildlife, which includes black bears, bobcats, and even spring salamanders! Another forestry area to check out is the Hopkins Memorial Forest, which is located by the Williams College. The Clark Art Institute welcomes leashed pooches on their outdoor grounds, so a hooman or two can head indoors to check out the art, while one sticks with the pooch and enjoys the grassy areas! When you and your pooch get hungry, there are a variety of local restaurants with pet-friendly outdoor seating to check out: Purple Pub offers pub food like burgers and sandwiches; and Coyote Flaco specializes in homestyle Mexican eats and margaritas.
The final town in the Berkshires that Luie Boone would suggest you visit is Lee! This town was a classic New England mill town, with working paper mills still found along the Housatonic River! If you're looking to shop with your pooch, the Lee Premium Outlets are generally considered pet friendly. Just be sure to double check pet policies before visiting. If you're looking for some more outdoorsy activities, there's no shortage of things to do! Check out October Mountain State Forest, which is an over 16,000-acre forest with deep forest trails that bring you to Woods Pond. Goose Pond Reservation is another must-see, as it's an over 100-acre nature preserve, offering swimming, kayaking, and canoeing opportunities! After a long day, visitors can stop at Starving Artist Café or Avocado Café to get a bite to eat. Both spots offer pet-friendly outdoor seating. Luie Boone heard you can get a sweet and savory crepe at the Starving Artist Café, and then tacos dorados at Avocado Café. Yum, yum, yum!
So, whether you're chasing waterfalls, sniffing out snacks, or just soaking up the scenery, Luie Boone says the Berkshires are a tail-wagging good time. Pack your leash, grab your treats, and let the adventure begin!
Paws Rest Here
Luie Boone paw-selected this perfect vacation rental for your stay in The Berkshires of Western Massachusetts. Check it out below!
Rental Name: The Heron House
This rental has 3 bedrooms with 6 beds and 3 bathrooms.
Photos are courtesy of VRBO.
It features the following amenities:
The house sits on 36 private acres
Private 2.5-acre lake
Large sunroom with a sofa bed
5-person hot tub, which is built into a large wraparound deck
Outdoor shower
Barbecue grill
Fire pit to make s'mores
Ping pong table
Well-maintained trails on the property
Across the road is a park, which has an additional hiking trail
What does Luie Boone think of this rental? He woofed:
Do you know what a heron is? It's a type of bird that is long legged and long necked. These birds are found in freshwater and coastal areas, which is exactly where we're heading on vacation to. In the Berkshires, we will be staying at the Heron House. I'll be bringing along Skipper, my trusted, but sneaky fox plushie! This house is located at the end of a long driveway with trees encompassing it. Those trees do open to a private lake, which means swimming, splashing, and chasing ripples until I flop over really happy and really tired! Skipper will enjoy my outdoor escapades from a safe place inside, looking out a window or perched up on a chair on the dock. Inside the house, there's a great big room with a fireplace—paw-some for naps. Outside, there's a deck that overlooks the water. The hoomans will sit in the hot tub, while I watch for ducks, turtles, turkey, red-winged blackbirds, and, of course, herons! At night, we'll sit around the fire pit and eat s'mores. The whole place sits on thirty-six acres, with trails to sniff and a park across the road with even more trails to explore. Skipper and I haven't even been there yet, but we can tell this place is ten out of ten bones!
Paws Venture Here
Luie Boone sniffed out and dug up these local gems for you to check out while vacationing in The Berkshires of Western Massachusetts.
Felton Lake
Luie Boone recommends that you spend some time at Felton Lake, which is one of the nicest lakes in Massachusetts. It is found at an elevation of 1,580 feet. You can hike the Gorge Trail to get to this remote lake. The trail provides a very relaxing outdoor experience, with the opportunity to appreciate both the forest and the lake! Luie Boone hopes there's a place to do a big cannonball. From the pictures, he can already tell there's spots to pose on logs and stumps for his hooman's cameras, as well as a big, beautiful lake to swim in.
Parsons Marsh
The Parsons Marsh is home to many wildlife and environmental ecosystems. Visitors and their canine companions can enjoy a short and easy, just over a half-mile walking trail. This trail takes you through a quiet open meadow, to a small pond, and then on a boardwalk through a forest and vegetated wetland! Sounds like an adventure to Luie Boone. Keen-eyed visitors can spot some of the 75 species of nesting birds, along with a host of other animals—including frogs, turtles, white-tailed deer, beavers, otters, foxes, black bears, and coyotes!
Stone Hill via Kite Hill Trail
The Kite Hill trail is a 2.9-mile trail, which walks along the perimeter of a field before entering into the woods. Some hikers will do the hike with their dogs off-leash, particular in the less busy early morning times. Later in the day, at busier times, it’s better for everyone if dogs are kept on leash. Don't forget to take a photo of your buddy on the stone chair at Stone Hill! Luie Boone reckons that he'll need a treat or two to get his little tooshie up there.
Mountain Meadow Preserve
The Mountain Meadows Preserve is a family-and-dog friendly hiking area. Here, visitors and their pups have several options for an enjoyable day of outdoor recreation in Western Massachusetts. Upon arrival at the parking lot, visitors will find a wide hiking trail through a dense forest. As, they traverse along this path, visitors will hike into an expansive meadow!
Monument Mountain
For almost two centuries, Monument Mountain has been a source of inspiration to poets, novelists, and painters. The summit offers panoramic views of Southern Berkshire County, and it has three miles of trails that lead through a white pine and oak forest. Want a history lesson? Well, On August 5, 1850, Nathaniel Hawthorne and Herman Melville enjoyed a well-chronicled picnic hike up Monument Mountain. A thunderstorm forced them to seek refuge in a cave where a vigorous discussion ensued, inspiring ideas for Melville's book, Moby Dick.
The Boulders
At this local gem, visitors and their canine companions can take a venture on a trail through fern meadows, which are surrounded by an open hemlock forest. The trail will take you to The Boulders. Now, these aren't just any boulders. The Boulders are large rock formations that erupt suddenly from the ground! Once you arrive at these boulders, there are scenic views of the Berkshires toward the west to enjoy.
Donato's Trail
On this trail, hikers and their pups can enjoy the beautiful landscape of the Goose Pond Reservation! The trail is a hilly hike, taking you through the towering trees. As you journey along, you can glimpse of Goose Pond through the trees. Luie Boone promises to not zoom through the trees to cannonball into the pond... maybe. The forest floor is colored with vibrant shades of green from this area's vast undergrowth, which ranges from ferns to mountain laurel.
'6 House Pub
This dog-friendly eatery offers a variety of dishes— including lobster rolls, crab cakes, burgers, shrimp scampi, and lobster mac and cheese. They serve craft beer and creative cocktails, which piques the interest of Luie Boone's paw-ther—a big time craft beer connoisseur. Luie Boone will get comfy by the outdoor fire, as his paw-ther guzzles them down. The pub also has vegetarian and gluten-free options available. Make sure to order from the dog menu, too! It features bark balls, chicken a la hound, and chilly paws! Luie Boone will have one of each, thank you very much.
Luie Boone's Pet Peeve about
The Berkshires of Western Massachusetts
There's just so much to love about this vacation destination, but there's one thing that's got Luie Boone's leash in a twist. He woofed:
The bark on the street is that my hoomans have planned a vacation to the Berkshires of Western Massachusetts. I've already packed my most important companion: Skipper the Fox. Let me tell you, Skipper and I are ready to sniff trails, splash in lakes, and charm every hooman that we met. I'm quite a charming fella. But then, I heard a word that made my ears perk up and my tail hang low: Skunks! Apparently, there are millions (actually thousands, sorry I'm an overexaggerating pooch), of skunks roaming around. Thankfully, it's mostly at night, but still! That's scary! So, I did what any responsible, reasonable pup would do: I Googled "how to skunk-proof your vacation." Don't ask how I type, just know that it involves a lot of nose boops and paw smashes. And guess what? Thanks to Google, I've got a paw-some plan. First, I’m packing my anti-skunk arsenal: tomato juice (not for drinking—unless things get really desperate), skunk-scent-repellent spray (smells like sadness and regret, but apparently skunks hate it), and an emergency chew toy (for stress relief, obviously). Second, I’ve enrolled Skipper and myself in a crash course called “Sniff, Don’t Chase: Wildlife Etiquette for Dogs.” It’s mostly just me watching nature documentaries and barking at the screen, but I feel enlightened. And finally, I’ve made a pact with the moon: no nighttime zoomies. If the skunks come out after dark, then I’ll be inside, curled up like a cinnamon roll, dreaming of bacon and belly rubs. So, fear not, fellow tail-waggers. The Berkshires may be skunky, but this dog’s got a nose for adventure and a plan for survival. Skipper and I are ready to roll—with charm, caution, and just a whiff of tomato juice. Now if you’ll excuse me, I need to go bury my hooman’s socks. It’s part of the plan. Don’t ask.
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