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5 Walking Trails In Massachusetts That Are Beautiful And Fun

By Carolyn Kruse

We all know walking is so good for us. But it can be boring. That’s why you should check out these 5 walking trails in Massachusetts that are beautiful and fun. You won’t be bored stepping up your game on these paths.

From everything I read on the subject, walking is great for your physical and mental health. It gets you outside in nature and gets your blood pumping! According to Better Health, “just 30 minutes every day can increase cardiovascular fitness, strengthen bones, reduce excess body fat, and boost muscle power and endurance.” That’s a lot in one simple walk!. No equipment needed, just a good pair of shoes, appropriate clothing and maybe a bottle of water. Did you know walking can also reduce your risk of developing various diseases, too? As mentioned in the article it can help reduce your risk of heart disease, osteoporosis, type 2 diabetes and some cancers.

Best Walking Trails In Massachusetts

Now, that we’ve established walking is THE exercise we all need, let’s go for a stroll. Here, you will find out about 5 of the absolute best walking trails in Massachusetts that are beautiful and fun. With my own personal knowledge of a few of these, along with help from the website, All Trails, wander through this short list of favorites. From historic wooded areas to cobblestone streets, there’s a little something for everyone here.

If you’re up for a more challenging or longer route, head up to Blue Hills. If water views are what you’re craving, Walden Pond is perfection. There are city walks and country side strolls. Most of these you’ll find to be over a mile and less than 5 miles. But if you really want to get those steps in, do a few loops at one of the below, or try alternate trails at the locations of a few of these fabulous walking trails in Massachusetts. Lace up…and march on! It’s good for you.

Walking Trails in Massachusetts

  • 5. Weir Hill Reservation Trail

    • ADDRESS: 65 Stevens St. North Andover
    • LENGTH: 2.6 mile loop

    Weir Hill (traditionally pronounced “Wire Hill”) in North Andover is is a 194-acre public park in North Andover, owned and maintained by the Trustees of Reservations. This popular  2.6-mile loop trail is only one of quite a few trails on the property. It’s pretty easy and should take you about an hour, on average, to finish.  Best of all, this trail is open year-round. By the way, your pup is welcome, but must be on a leash. The walks “include a shimmering lake shoreline, an expansive panorama of the Merrimack Valley, and the diversity of ten different types of plant communities,” according to the Trustees website. You’ll find 4 miles of trails ranging from easy, like the Reservation trail to difficult.

    Weir Hill

    Trace the western shore of Weir Hill's sparkling lake or enjoy a woodsy ascent to scenic views of the Merrimack Valley. 4 miles of trails.

  • 4. Arnold Arboretum Trail

    • ADDRESS: 125 Arborway, Boston
    • LENGTH: 3.7 miles

    Springtime on this trail is breathtaking, once the Cherry Blossoms are in full bloom. The Arboretum is  near Jamaica Plain. You’ll find the trail to be a “walk in the park.” It’s an easy one and should take you around 1 hour and 23 minutes.  Generally considered an easy route, it takes an average of 1 h 23 min to complete. This is a very popular area for birding, fishing, and hiking, so you’ll likely encounter other people while exploring. The best times to visit this trail are March through October. Dogs are welcome, but must be on a leash.

    The spring landscape is more colorful every day. Share your photos on Instagram with #MyArnoldArb for a chance to be featured in our feed!1: @katie_kta2: @project_artbold3: @mydailyjppond

    Posted by Arnold Arboretum of Harvard University on Saturday, April 6, 2024

  • 3. Boston's Freedom Trail

    • ADDRESS: Freedom Trail, Boston (at Boston Common at 139 Tremont St.)
    • LENGTH: 3.1 miles

    I know, I know. It’s a touristy thing to do, but EVERYONE should do this walk, guided or on your own. And do it more than once, it’s history in a decent amount of walking if you are worried about getting in your steps. The historic trail should take you roughly an hour to complete. It’s mostly flat and you can bring your dog on a leash. The Freedom Trail is open year round and it’s a beautiful way to see and celebrate our city and it’s history. FYI: Freedom Trail visitor centers are located at Boston Common, Faneuil Hall, and the Charlestown Navy Yard. You’ll see everything from Paul Revere’s house to the Granary Burying Ground, the Old North Church, Bunker Hill Monument and Old Ironsides (The USS Constitution). Breathe in our beautiful and legendary city. Spring time is an awesome time to walk the trail, before it gets too hot.

  • 2. Walden Pond Path

    • ADDRESS: 915 Walden St. Concord
    • LENGTH:  1.9 mile loop

    If you don’t have a lot of time, this stunning trail with water views for days will soothe your soul. It’s an easy stroll through hallowed grounds. Leave your pup at home though, because NO dogs are allowed. This route takes about  37 min to walk. It’s a super popular area for walking, hiking and bird watching, so you won’t be alone. Heads up: Walden Pond State Reservation does charges a daily entrance fee. Don’t miss an opportunity to walk where Henry David Thoreau walked and lived amongst the trees.

  • 1. Great Blue Hill (Via Skyline Trail)

    • ADDRESS: 1905 Canton Rd. Milton
    • LENGTH: 3 miles

    It’s all about the view! I’ve been hiking Blue Hills Reservation for many years and there nearly an infinite number of ways to walk the glorious forests in the Blue Hills Reservation.. But this 3 mile loop, known as the Skyline Trail, is moderately challenging and should take about an hour and 45 minutes. There are amazing views of downtown Boston once you reach the top and climb up Eliot Tower. As explained in All Trails, you should take the “blue-blazed Skyline Loop Trail begins behind the park headquarters. Take the stone steps up Hancock Hill and follow the winding footpath over the ridge line to Eliot Observation Tower, which sits atop Great Blue Hill. Climb the tower for a panoramic view. To return, cross over the stone bridge to intersection #1066, and turn left to return via Skyline south.”

    View of Boston from Blue Hills

    We soaked in a view of Boston from just off 95 by hiking the Blue Hills in Milton, MA!Tips:📍Don’t blindly type “Blue Hills” into your GPS! Be sure to use “Blue Hills Trailside Museum” (1904 Canton Ave) and not “Blue Hills Reservation” (the other side of the park)🥾 The hike is mostly walking with some notable scrambling up rocks. I’d pack some band-aids just in case— the rocks were more slippery than we were used to (which my kids loved for sliding on the way down!) Our 3-year-old was definitely the youngest I’d take without a carrier, and it took us about 45 minutes to reach the summit at our slow pace (would have been 25-30 minutes up with older kids)🧺 There are shaded picnic tables at the base of the observation tower, making it a perfect lunch spot 💦 Pack more water than you think you need— I was wishing for some frozen bottles waiting for us in the car!🚽 There are bathrooms (free) but be aware that you’ll need to walk pretty far through the animal exhibit area behind the museum to get there. It was probably an extra 0.2 miles to get from the parking to the bathrooms and back. 💰 Parking is free and there are rescued animals to see for free outside the museum near the parking lot (deer, red foxes, turtles, otter). The only way to spend money here is if you go inside to see the snake and birds of prey indoors (free for Mass Audubon members) or check out the gift shop (stocked with snacks)Enjoy your visit to the #bluehills this fall!

    Posted by Community Kangaroo on Sunday, August 21, 2022

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