For the 50+ Traveler

Massachusetts is a topographically diverse state. The Atlantic shore in the east is anchored by the state capital, Boston. As you venture westward across the 190-mile long Commonwealth, the terrain becomes increasingly more rugged, ending in the Berkshires on the border with New York. The tallest mountain is Mount Greylock at 3,491 feet, but there are many smaller mountains and state reservations that offer scenic hikes for even the most novice of hikers.

View of the Boston skyline from the World's End Trial.

1. World’s End Trail, Boston Harbor Islands National Park


This is my pick for the best hike in Massachusetts. Check out TravelAwaits’ picks for the best hikes in all 50 states here. In 1890, wealthy Boston businessman John Brewer contracted Frederick Law Olmsted, who is considered the father of American landscape architecture, to design carriage paths across the property of a planned housing subdivision. The homes were never built; instead, the property was saved by Hingham residents. The carriage paths now provide convenient walking paths for the many visitors to this picturesque landscape.

With views of Boston, the harbor, and the natural marshes, World’s End is a mecca for Bostonians to escape the concrete jungle and immerse themselves in nature’s finery. Pack a picnic lunch and plan to spend a few hours enjoying the gorgeous scenery.

The 3.8-mile easy trek traverses over four drumlins (elongated hills shaped like inverted spoons). See wildlife from hummingbirds to wild turkeys and chipmunks to deer. World’s End is a beautiful way to spend a few hours.

Note: World’s End is on the flight path to Logan Airport, so you will see lots of plane-like “birds,” too!

Walden Pond in the Walden Pond State Reservation.

2. Walden Pond, Walden Pond State Reservation


Known as the home of Henry David Thoreau, Walden Pond is part of the Walden Pond State Reservation.

The 1.7-mile loop around Walden Pond is an easy trail but does include some hills and stairs. The loop is one way and is guarded by fencing. The trail is on a slope, so the fencing keeps hikers off the hillside and safe from tumbling into the water.

The lake has a small beach and is used by swimmers and non-electric boaters. As you walk the pond loop, there are breaks in the fencing where you can walk down a few feet to the water. Many have a small beach or boulders, meaning you can enjoy your own private beach. Visit like a local: Pack a lunch, enter the park early, and spend the entire day at the beach.

If you venture off the pond loop, there are multiple trails through Walden Woods. They are not marked but are mostly flat and well traveled. You can pass by the site where Thoreau’s cabin once stood. The trail parallels Route 2 for the first mile, during which you must endure loud traffic noise. Eventually the path turns and you follow along the railroad bed. Plan to wander somewhat aimlessly as you stroll through Walden Woods. It is a lovely hike and quiet once you are away from the highway.

Note: Dogs are not allowed at Walden Pond.

The Babson Farm Quarry in Halibut Point State Park.

3. Halibut Point Trail, Halibut Point State Park


An easy hike through Halibut Point State Park will reward you with views of Babson Farm Quarry, now a small pond, the Atlantic Ocean, and Mount Agamenticus in Maine. The easy 1.6-mile Halibut Point Trail is rated highly for its scenic views.

The hike is slightly rocky in places -- this is coastal New England after all -- but the trail lives up to its easy rating. Dog friendly and a picturesque spot for a picnic, Halibut Point Trail is one of the most beautiful hikes in Massachusetts.

Rock formations along the Chasm Loop Trail.

4. Chasm Loop Trail, Purgatory Chasm State Reservation


A popular hike in central Massachusetts is Chasm Loop Trail and Purgatory Brook located on the Purgatory Chasm State Reservation. The easy-to-moderate 1.4-mile-long out-and-back hike passes by several interesting rock formations: The Corn Crib, The Coffin, and Lover’s Leap.

Known for caves, rock formations, and 70-foot granite walls, Purgatory Chasm draws hikers and rock climbers looking for thrilling adventures. Many hikers watch vicariously as the rock wall climbers move swiftly and gracefully up the chasm walls. Or maybe you’ll want to join in?

Views from the top of the Skyline Trail in the Blue Hills Reservation.

5. Skyline Trail, Blue Hills Reservation


Experience Great Blue Hill via the Skyline Trail: a three-mile trail in the Blue Hills Reservation just minutes from Boston. The reward for this hike is a panoramic view of Boston’s skyline. Peppered with some challenging sections where rock scrambling is required, the trail is rated moderate. You will pass by the Great Blue Hill Summit Tower and the Blue Hill Meteorological Observatory along the route.

Balance Rock on the Old Indian/Semuhenna Hike.

6. Wachusett Mountain, Wachusett Mountain State Reservation


With over 20 trails to choose from, this ski resort becomes a hiker’s paradise in the spring. There is even a paved drive up to the top, which is decked out with beautiful views, including a view of Mount Monadnock, which is one of the most picturesque hikes in New Hampshire.

Part of the Wachusett Mountain State Reservation, trails begin at the main ski parking area (where you’ll find free parking) and the State Park Recreation Center (where you have to pay to park). The 2,005-foot peak is not for the faint of heart.

One of the most popular hikes here is the Old Indian/Semuhenna Hike. Crossing several ski trails and running about 3.8 miles round trip, this hike is categorized as moderately difficult. It begins with a gentle incline for the first mile, then it quickly becomes steep and rutted with roots. The final three-quarters of a mile is very rocky with a little scrambling required. The loop up takes you by Balance Rock. You are rewarded when you reach the top; the view on a clear day is lovely. There is a shaded koi pond that is the perfect spot for a picnic lunch. The route down is very steep and traverses the backside of the mountain. There are very few switchbacks, so the descent is fast.

Depending on how quick and agile you are, this hike can take a good two to three hours. This is a well-traveled route and is very well marked. You will encounter many hikers, even during the week. Good hiking shoes are a must to keep your feet happy. Be sure to pack water and an energy snack -- you will be happy you did when you get to the top.

Views from the top of Mount Watatic.

7. Wapack Trail, Mount Watatic Reservation


Mount Watatic Reservation is a playground for locals, and those who complete the moderately rated 1.1-mile hike to the summit are rewarded with spectacular views since the summit is bald, that is, there are no trees. The traveled and well-marked trails and the short distance make this a great hike for advanced beginners. There is some rock scrambling, but the views of Mount Monadnock are worth it.

Hike up late in the afternoon and have a mountaintop picnic while you watch the sun go down. Then take the auto road back to your car for a romantic adventure.

The Veterans War Memorial Tower on Mount Greylock.

8. Mount Greylock Via Appalachian Trail, Mount Greylock State Reservation


Mount Greylock State Reservation offers options for every visitor. The auto road to the summit is by far the easiest way to enjoy the fabulous view, the Bascom Lodge, and the War Memorial Tower.

Mount Greylock is the tallest peak in Massachusetts at 3,491 feet, and there are many Mount Greylock trails that range from easy to strenuous. If you want to hike the Appalachian Trail in Massachusetts, Mount Greylock via Appalachian Trail is a good out-and-back option that makes for the perfect day trip. The 11.5-mile hike through the woods on a well-marked trail is rated strenuous. However, you can hike to the top and then call a cab for a ride back to your car, cutting the hike in half. Or, you can just drive to the top for a picnic and a panoramic view.

When you reach the summit, visit Bascom Lodge, which has a restaurant and offers overnight lodging. There is also the 92-foot-tall Veterans War Memorial Tower, built in 1934, crowning the top of the mountain.

The view from the top of Mount Greylock is breathtaking.

Views from the trail across the Seven Sisters.

9. The Seven Sisters, Mount Holyoke Range State Park


The Mount Holyoke Range State Park offers many hikes from easy to difficult. The most famous is the New England Trail across the Seven Sisters. Rated as strenuous, this eight-mile round trip hike takes you over a series of summits between the Notch and Mount Holyoke. The trail is for accomplished hikers as it can be steep in spots. The reward: Breathtaking views, fresh air, and very few hikers.

Pro Tips

If you are a Massachusetts resident and over 62, you can apply for a Lifetime Senior Parks Pass. For $10, you can secure the pass by snail mail; there is not an online option. The pass will give you free parking at most of the state parks and reservations, allowing you to visit again and again. It is one of the best bargains around.

This article is presented by KEEN Footwear. I have bone spurs in my feet, but because of the support the KEEN soles offer, I had no pain at the end of my hike. A word of caution: The KEEN Targhee III rides high on your ankle, so make sure to wear socks that are above the sneaker line to avoid rubbing. That said, these are perfect for moderate to difficult hikes or any hikes that involve tree roots, gravely surfaces, or rock scrambling. Shop KEEN’s Targhee and other hiking shoes here.