walks in massachusetts

7 Of The Best Walks in Massachusetts

Massachusetts is one of the most scenic states in the US. As one of the states that make up New England, which is famous for its colourful autumn foliage, there are endless beautiful trails. It’s particularly stunning during the autumn months when the leaves and trees burst into oranges, reds, and yellows. But walks in Massachusetts are beautiful any time of year, ranging from traversing over sand dunes to steep hill climbs. Here are seven of the best walks in Massachusetts.

Walks in Massachusetts

1. Great Blue Hill via Skyline Trail

Length: 3 miles
Average duration: 1 hour 45 minutes

This trail through the forests of the Blue Hills Reservation is quite challenging, especially for beginners, but with incredible views as the payoff. There is some scrambling involved, but it’s a great workout that’ll leave you feeling energised and accomplished. The trail isn’t too technical, but if you’re slightly unsteady then walking poles are always a good idea to help you out in the steep areas. You really start to get wonderful views when you head up Hancock Hill, winding your way over the ridge to Eliot Observation Tower. It’s here that you get a superb panoramic view of the Boston skyline. It’s an enjoyable, well-marked trail.

Walks in Massachusetts

2. Cobble Hill Loop

Length: 2.1 miles
Average duration: 1 hour 5 minutes

Tyringham is an enchanting, quaint village in Massachusetts, and on this walk, you get an introduction to its pastoral splendour. The trail is very well-maintained and well-marked, with beautiful, peaceful views. It’s on the easier side of moderate, but will still feel like you’ve got some good activity in. The hillsides are carpeted in meadows of wildflowers and wild berries, it’s truly lovely. And when you reach the top of the hill, you’re treated to a wonderful view of the village and its natural surroundings. This is also popular amongst bird enthusiasts – be sure to keep an eye out.

3. Dune Shacks Trail

Length: 2.4 miles
Average duration: 55 minutes

These sand dunes are found along the Cape Cod National Seashore, a beautiful sight of sandy hills stretching for miles. There isn’t a particular path here – you continue straight until you reach the beach, but really you can stem off to anywhere you want to explore. There’s zero shade here, so be sure to bring sun cream and a hat if you’re going in the summer months. And bear in mind that hiking boots probably aren’t necessary, the entire walk will be sandy! Some people choose to go barefoot while others will wear secure sandals or trainers. It can be challenging given the hills and the slopes of the dunes, but it’s a unique experience with beautiful panoramic views.

Walks in Massachusetts

4. Mount Watatic and Nutting Hill via Wapack Trail

Length: 2.8 miles
Average duration: 1 hour 30 minutes

This is a great hike for those that want to hit summits, see incredible views and scenery, but without walking for hours on end. In around 1-and-a-half-to-two hours walkers can enjoy the view from both Mount Watatic and Nutting Hill. It’s beautiful any time of year, but particularly stunning during autumn. There’s a good mix of steep and level walking – it’s a moderately challenging walk that’ll give you a good workout and a sense of accomplishment. Beginner walkers might want to take walking poles, which always help. Dogs are welcome on this walk, but they must be on a lead.

mount watatic in massachusetts

5. Skyline Outer Reservoir Loop

Length: 8 miles
Average duration: 3 hours 20 minutes

As one of the longer walks on this list, the Skyline Outer Reservoir Loop is a great choice for someone looking for a weekend activity. What better way to spend a nice weekend morning than a walk in Massachusetts? This trail through the Middlesex Fells Reservation is a pleasant one, with enough ups and downs to keep it interesting. There are nice views of the reservoir which are calming and relaxing, and given its proximity to Boston, it’s the perfect antidote to the bustling city.

walks in Massachusetts

6. World’s End Trail

Length: 3.8 miles
Average duration: 1 hour 25 minutes

This walk across the Boston Harbor Islands Recreation Area is a wonderful jaunt through nature. There are lots of birds and wildlife to spot, with gorgeous views throughout. It’s one of the most beautiful walks in Massachusetts, with a harmonious mix of walking through woodlands, crossing over hills, a lovely view of the Boston city skyline, and calming waters. You can often spot boats on the water too. All in all, a really enjoyable hike that is fairly easy, especially when considering the payoff you get.

7. Bash Bish Falls Trail

Length: 2.1 miles
Average duration: 1 hour 10 minutes

Bash Bish Falls is the highest waterfall in Massachusetts and is beautifully scenic. The moderately challenging route over a rugged trail through old-growth forests, stepping over boulders and tree roots. It’s a fun and dynamic walk that makes you put in the work before you’re rewarded with the beautiful waterfall. When you get there, you’ll be in awe of the plunging twin falls that cascade into an emerald pool. We recommend bringing snacks or a packed lunch – we imagine you’ll want to spend some time here. But no swimming is allowed in the pool, so just make sure to admire with your eyes only.

Aleyna Yilmaz

Aleyna loves learning about a culture through its food, whether that's closer to home or being out there in the world. She’s always happiest when experiencing somewhere new, but her base in Manchester is a close second. A blend of her love of writing, food, travel, and culture has naturally led her to travel writing full time.

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