Outdoor Recreation

Hiking With Dogs

Some of our favorite hiking destinations with our best furry friends.

Looking for the best properties to walk your dog?

For many, their go-to hiking companion is their dog. The Trustees has a long history of welcoming dogs to most (but not all) of our properties. Most reservations require dogs to be on-leash at all times. A few reservations allow dogs off leash. And some do not allow dogs at all or on certain portions of the property, in order to protect livestock, farm fields, wildlife nesting grounds, and cultural resources. Dog-walking designations are listed on each property’s webpage and on signage as you arrive at the reservation.

If you do choose to bring the pup along for an outdoor adventure, we do ask that you please heed property signage regarding dogs and follow our mindful dog-walking behaviors: RECOGNIZE, RESPECT, REMOVE.

RECOGNIZE that other visitors may not be comfortable being approached by dogs and that not all dogs like other dogs. Share the trail and ask first before letting your dog approach others.

RESPECT our conservation efforts and the resources we are trying so hard to protect. Keep dogs on trails, and do not allow your dog to chase or harass wildlife, or disturb, or destroy vegetation.

REMOVE your dog’s waste–it’s bad for the environment and wildlife and makes for an unpleasant experience for others. Bag it and carry it out! Please bring and use your own biodegradable poop bags, dispose in designated receptacles (if available), or pack it out with you to throw away at home.

Here are some of our favorite dog hiking destinations.

Lowell Holly 4 miles of carriage roads and paths coupled with two freshwater ponds make Lowell Holly a great place to hike with a dog. Enjoy the pup-friendly trails and sandy freshwater beach to cool off on a warm spring day.  

Moose Hill Farm Farm meets forest at this beautiful property south of Boston. On a clear day you’ll be welcomed by some amazing insta-worthy views of the Great Blue Hill and the Boston skyline. Note the adjoining Mass Audubon property does not allow dogs.

Tyringham Cobble Get a taste of the Appalachian Trail while hiking through the fields and forests of Tyringham Cobble. Beautiful Berkshire vistas are beloved by dogs and hikers alike.

Jewell Hill One of our newest properties and another property you and your dog will love. Meander through grassy meadows and take a short uphill trek to the top of Jewell Hill, and you’ll be rewarded with a 50-mile view of the Boston skyline.  

Mary Cummings Park This property is great for hikers and dogs that are just getting their feet wet with hiking. Flat paths, no elevation gain, and plenty of benches to rest make this an ideal hiking spot for those hikers and dogs looking for a slower pace.   

Two Mile Farm High mileage seekers need not apply. This is a short and sweet walk for small or elderly dogs or for the hiker who wants to breathe in some salt marsh air.

Swift River Reservation Swift River Reservation has over 5 miles of trails along the historic Swift River, perfect for hikers with high energy dogs. For extra mileage also explore Brooks Woodland Preserve, just one mile down the road from Swift River and also dog friendly.  

Our Favorite Dog Hiking Destinations
More Hiking Ideas

Join the Trustees

Enjoy 120 sites featuring inspired trails, historic homes, beautiful gardens, farms, summer camps and more.
Become a Member

Lend a Hand

Join a community passionate about a sustainable future and engaged in diverse projects across the state.

Support Our Work

We rely on your generous support to protect the irreplaceable landscapes and landmarks of Massachusetts.