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 recreational opportunities are abundant enough to make Pittsfield the literal and cultural heart of the Berkshires.
Pittsfield, MA makes the perfect getaway for both humans and dogs, and while you’re close enough to explore all of the best attractions in the Berkshires, you’ll find plenty to do without leaving the city limits.
Here’s an itinerary for three perfect hours to explore the best things to do in Pittsfield, MA — with dogs, of course!
Enjoy Pittsfield’s First Dog Park in Burbank Park
Have your dogs been impressing you with their exemplary behavior and charming ways? Reward them with a visit to Pittsfield’s sprawling, shady dog park in Burbank Park.
This large off-leash park includes two separate fenced-in areas, one for small dogs and one for large dogs (or small dogs who think they are large dogs). There are benches for the humans to sit on, and lots of trees for dogs to pee on.
This is the perfect spot for friendly dogs to enjoy some freedom and make some friends.
Grab a Bite at Dottie’s Coffee Lounge
Dottie’s Coffee Lounge‘s dog-friendly patio is one of the best spots in Pittsfield. Order a vegan BLT or mocha latte, and be sure to check out the retail offerings that include bear butter and tasty dog treats for your well-behaved companions.
Journey Through Pittsfield State Forest
11,000 acres, 30 miles of trails, and a 165-boulder that appears to defy gravity. Welcome to Pittsfield State Forest, a wild enclave of mountains, ponds, and woods just outside of the city. Before leaving town, pick up a bagged lunch from Marketplace Cafe for a mountaintop picnic.
Here are a few of our favorite spots in Pittsfield State Forest — note that because Pittsfield State Forest is so massive, you will have to drive between these spots.
Shaker Mountain: The trail to Shaker Mountain begins at Hancock Shaker Village and travels past the site of a former Shaker settlement and a holy site on top of Shaker Mountain (1,845 feet). The trail can be tackled as a 6.5-mile loop, or you can just hike up to Shaker Mountain and back, which is 2.6 miles. There are no vistas, but the woods are lovely!
Balance Rock: This giant glacial erratic was deposited in this spot 13,000 years ago, and while it seems like it could topple from its perch at any moment, so far its massive size and weight have kept it in place. Visit Balance Rock from Balance Rock State Park in Pittsfield State Forest.
Lulu Cascade to Berry Pond: This 5.2-mile loop has everything — a beautiful brook, a small cascade, wildflowers, and panoramic views.
Berry Pond Driving Loop: If you don’t have time for a hike, you can drive the Berry Pond Circuit Road to the top of the hill, where you’ll find the perfect picnic spot. From there you can walk down to Berry Pond.
Experience Authentic Italian Flavors at Trattoria Rustica
Not only is Trattoria Rustica one of the coziest eateries, but the service and food both exceed expectations. Cozy nooks indoors are surrounded by warm brick and stonework, and the outside patio is shrouded in greenery.
The whole place feels like it was transported directly from Italy to the Berkshires.
With an impressive wine list and a traditional Italian menu, Trattoria Rustica invites patrons to relax into a memorable sensory experience through dishes like stuffed sea bass and eggplant melenzane, both roasted in a wood-fired oven and cooked to perfection.
Reservations are suggested and dogs are permitted on the patio.
Catch the Sunset Over Onota Lake
Escape the downtown area for a spell and head to the shores of Onota Lake where your dogs can swim and you can enjoy the warm glow of the setting sun as it sinks behind the mountains.
This 617-acre gem of a lake is located entirely within the City of Pittsfield.