Tails, Trails & Travels Across the U.S.

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This is our journey to discover the most dog-loving places in America, one adventure at a time.

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5 of Our Favorite Dog-Friendly Trails in Lexington, MA

  1. Willard Woods

There are multiple trailheads for Willard Woods. The main trailhead as a small parking lot and others are located at the end of residential neighborhoods. The best part about Willard Woods is that dogs under good voice control are allowed off-leash Monday through Friday. All dogs must be on-leash on weekends. The outer loop around Willard Woods is about one mile. There is diverse terrain including wide open fields, woods, a small pond, and some streams. We had very pleasant interactions with both the dogs and owners here.

2. North Street Pits

This trail is about 1 miles long and takes you in a loop around on small pond and then a larger pond beside it. There is only space for 3 cars if you park on North Street, so I opted to park a little bit further down where there is a paved parking lot for the Across Lexington trail. There is a connecting trail to the North Street Pits loop from the Lower Vine Brook Path. This also helped to elongate our walk a bit. One side of the loop around the ponds has a very well defined trail, but the furthur side is not well defined and there are no markers. However, if you just follow along the edge of the pond you cannot get lost. You could also opt to use the All Trails map. I found this trail to be very quiet and Max enjoyed swimming in the larger pond.

3. Old Reservoir Loop

This trail is about 0.5 miles around an old reservoir. You can access the loop from the trailhead located behind Bridge School. It can be awkward during the weekday when the kids are in school because you kind of have to cut through their recess area to get to the trailhead. There are two loops around the reservoir. One is a paved trail on the outer most loop, separated from the inner dirt trail by a chain-link fence. There is a fenced off beach area that is off-limits to dogs. There are plenty of places along the trail with access to the water if your dog wants to swim.

4. Whipple Hill

We did about 2 miles of hiking through Whipple Hill, but since there are tons of trails and all of them intersecting you can choose your own adventure and how long you want to hike for. The trail is a mix of woods and fields, and borders the Locke Farm area. The loop around Locke Pond was nice and gave Max the opportunity to swim. There are multiple parking lots to choose from, but if you park at the Whipple Hill/Locke Farm lot you can see some alpacas by the trailhead. What I liked about this trail is there are some good inclines that make you feel like you got a good workout in. I definitely needed the All Trails app to not get lost because there are so many intersecting trails. Dogs are allowed off-leash on most of the trails here if under good voice control. I noticed it is a popular spot for dog walkers.

5. Minute Man Historical Park

Minute Man Historical Park is located partly in Lexington and partly in Concord. Battle Road trail to William Smith House is a 3 mile out and back trail located on the Lexington side. The trail is a wide, flat gravel path that mostly follows route 2A. There are some cool historical sights to stop at, like the spot where Paul Revere was caught. We stopped in one of the grassy areas to have a picnic, which was very nice. Be aware, you will share this path with many runners and bicycle riders. If you are looking for an easy stroll with some history this is a great trail.

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