The journey of life is sweeter when traveled with a dog.” —Unknown

If there is one thing dog walkers know better than anything, it is that whatever path you choose, a walk is always better with a dog by your side. National Hiking Day, or Take a Hike Day, is celebrated every November to encourage people to get outside and take advantage of the over 60,000 miles of hiking trails the United States has to offer. And what better way to enjoy those trails than with your favorite furry friend by your side? If you are a dog owner living in the Daily Leash service area of Holliston, Hopkinton, Ashland, Sherborn, Medway, and Milford Massachusetts you are in for a treat! The beautiful landscapes and lush greenery in this region offer an abundance of hiking opportunities that both you and your four-legged friend will love. Read on to explore some of the best local spots to hike with your dog and get some pro tips from your favorite Daily Leash dog walkers.

Upper Charles Rail Trail, Milford, MA

The Upper Charles Trail is a fantastic option for a scenic walk with your dog. The trail meanders through marshes and along the picturesque Charles River on an abandoned railroad bed. Milford was the first town to open a complete 6.58-mile section of the trail, when finished the path will cover 25 miles linking the communities of Milford, Ashland, Sherborn, Holliston, and Hopkinton (five of the six towns served by Daily Leash). The Milford section extends from the town center north to the Hopkinton town line, east into Holliston, and south to the Milford Senior Center, offering beautiful views and an easy and well-marked path. Keep your pooch on a leash and enjoy a peaceful hike in this serene setting or check out some of the many wooded paths and trails that branch off from the Rail Trail. Pro tip: The Upper Charles Rail Trail is a hot spot for runners, walkers, and bikers. It also crosses several busy roads. Be considerate of others and aware of your own dogs social limitations when walking this trail. Also take some time to check out some of the wooded paths and trails off of the main rail trail, particularly around Louisa Lake in Milford, Rocky Woods at the Milford/Hopkinton town line, and Wenakeening Woods (mentioned below) in Holliston.

Ashland State Park, Ashland, MA

Ashland State Park is a haven for nature enthusiasts and their dogs. The park boasts over 470 acres of woodland, meadows, and a large reservoir. Your dog will love exploring the trails, and even a quick swim to cool off during the warmer months. Although dogs are not permitted in the designated beach/swimming area during the summer season, there are plenty of spots along the trails where your pup can pop into the water for a dip. Pro tip: Ashland State Park charges parking fees from May 14 – Labor Day and in park parking is closed during the winter months, but you can skip the fee and have easy access to the trails and water by parking year-round at the boat launch off of Spring Street. Leash laws are in place throughout the park, but are rarely enforced.

Rocky Narrows Reservation, Sherborn, MA

If you are looking for a more challenging hiking experience, Rocky Narrows Reservation in Sherborn is a great spot to try. The trails wind through beautiful woods and along the Charles River, providing stunning views and incorporating an array of incredible sights, including 50-foot rock walls that date back 650 million years. Off-leash dog walking is permitted at the 274-acre Trustees of Reservation property, provided that your dog remains in control at all times and you pick up and carry out any waste.

Hopkinton State Park, Hopkinton, MA

Hopkinton State Park is a local favorite for outdoor enthusiasts and their furry companions. The park features a variety of trails, catering to different skill levels, including a popular loop trail that circles the parks picturesque lake. Dogs are welcome on leash and can join you for picnics, swims, and hikes in this beautiful setting. Although dogs are not allowed in the two designated beach/swimming areas from May 1 – September 15, there are plenty of places off the trails for your pup to jump into the water for a quick swim. Pro Tip: Many trails at Hopkinton State Park are multi-use trails, so you may come across others cross-country skiing, horseback riding, mountain biking, or even snowmobiling. Watch for signs indicating trail usage and always be aware and considerate of others on the path.

Wenakeening Woods, Holliston, MA

Wenakeening Woods in Holliston is a hidden gem for dog-friendly hiking. The network of trails takes you through a diverse landscape of woodlands and wetlands, connecting to the Idylbrook Loop and Recreation Area of neighboring Medway, MA. With relatively flat terrain, it is an excellent choice for a relaxed stroll with your pup. Parking is available at trailheads on Summer Street and Highland Street, and pedestrians may access the area by way of the Holliston portion of the Upper Charles Rail Trail (mentioned above). Pro-tip: Be aware, that while dogs are required to remain on leash at all times in Wenakeening Woods, this law is often ignored, particularly during the warmer months.

Exploring the great outdoors with your dog is not only a fantastic way to enjoy the natural beauty of your local area, but also an opportunity to strengthen the bond with your furry friend. Whether you are a resident or just passing through the area, these local hiking spots offer a range of options to suit your preferences and your dogs energy level. So, grab your leash, lace up your hiking boots, and embark on an adventure — the trails await!

For more information about any of the parks listed above, click the links in the parks’ descriptions for hours and amenities, as well as trail maps.

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