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Best Local Family Friendly Winter Hikes

Explore the Most Scenic Trails

By Kate Rushford January 13, 2025


Winter is the perfect time to get outdoors and enjoy nature with your family—and some of the best family-friendly winter hikes are right in and around our area. Many of these trails are also dog-friendly, so your furry family members can join in the fun. Here are some of the best spots to explore:

  1. Elm Bank Reservation, Wellesley, MA
    • This 160-acre reservation offers family-friendly trails, perfect for a winter walk. TheElm Bank Trail takes you through open fields and woodlands, and leashed pets are welcome. The trails are easy to follow, making it a great winter destination for families with dogs.
  2. Cutler Park, Needham, MA
    • The Cutler Park Trailoffers easy-to-navigate paths through woodlands and wetlands, with plenty of open space for pets to enjoy the snow. This dog-friendly trail is perfect for a winter hike with the family and is an excellent choice for families with dogs looking for a winter adventure.
  3. Wilson Mountain Reservation, Dedham, MA
    • With 400 acres of woodlands and several trails to explore, Wilson Mountain Reservation offers winter hiking for families and dogs alike. The Wilson Mountain Trailprovides moderate difficulty and scenic views of the surrounding area. 
  4. The Weston Reservoir, Weston, MA
    • The Weston Reservoir Trailoffers a 2.5-mile loop with views of the water and surrounding woods, making it a great winter hiking option for families with dogs. The trail is manageable and scenic, with pets welcome on-leash, so you can enjoy a serene winter walk around the frozen reservoir.
  5. Centennial Reservation, Wellesley, MA 
    • Centennial Reservation, a 55-acre park located in Wellesley, offers easy-to-navigate trails that are perfect for winter hiking with the whole family, including your furry companions. The Centennial Trail loops through a mix of woodlands and meadows, and the area is dog-friendly, so pets on leashes can join in the fun. The peaceful atmosphere and beautiful views make this a wonderful spot for a winter hike. The park is easily accessible and ideal for families looking for a short but scenic outing with their dogs.

Before heading out, be sure to dress warmly, pack water and snacks, and check trail conditions for any snow or ice. Winter hiking is a great way to enjoy nature with the whole family, including your four-legged friends.