Best Hikes in the Berkshires

If you’re looking for great outdoor adventure year-round, look no further than the Berkshires! This beautiful region in western Massachusetts is home to some of the most scenic hikes in the country. We’re partial to a visit to South County, but no matter where you stay during a trip to the Berkshires, you’re bound to find amazing views and incredible hiking. So whether you’re a beginner or an experienced hiker, we wanted to share our list of our favorite hikes in the Berkshires.

We wanted to share some of our favorite trails in the Berkshires and provide you with all the information you need to get started. So grab your backpack, and some delicious snacks and get ready for an amazing journey!

1. Benedict Pond Loop Trail

benedict pond loop trail - great barrington ma

Located in Beartown State Forest, this easy hike is one of the most accessible Great Barrington hikes. At less than 2 miles long and with no steep sections, this leisurely hike makes its way around a peaceful pond surrounded by forested hills.

The trail is open year-round and is popular for snowshoeing in the winter, earning it a spot among the best winter hikes in the Berkshires.

This is just one of many walking trails in the Great Barrington area. For more information about even more Great Barrington hikes, check out the Berkshire Natural Resources Council. They offer great tips and advice about hiking throughout the region.

2. Olivia’s Overlook

olivias overlook - lenox, ma

Olivia’s Overlook is one of the best hikes in the Berkshires. The well-marked trails are easy to follow. The views from the top are spectacular, making Olivia’s Overlook a great place to take a break and enjoy the scenery.

The Berkshire Natural Resources Council has rated this hike one of the best fall hikes in the Berkshires. This hike is also great in winter when the leaves are off the trees, and you can see for miles.

So, whether you’re looking for a challenging hike or great views, Olivia’s Overlook is among our favorite walking trails the Berkshires has to offer.

3. Hoosac Range Trail

hoosac range trail

This is one of the best hikes in the Berkshires for a few reasons:

  • It’s absolutely beautiful. The 360-degree views from the top of Hoosac Mountain are incredible – you can see for miles in every direction.
  • It’s a great workout. The hike is about four miles round-trip, and it’s pretty challenging, with some steep sections and rocky terrain. But trust us, it’s worth it!
  • This hike is perfect all year, especially in the fall and winter. In the fall, the leaves are changing, and the air is crisp. In winter, the beautiful views are even more breathtaking, with a dusting of snow on the ground and the trees.
  • Hoosac Range Trail is maintained by the Berkshire Natural Resources Council, so you know it’s well-maintained and eco-friendly.

4. Monument Mountain

monument mountain - great barrington, ma

Are you looking for a challenge? Or maybe you just want to enjoy a leisurely stroll with incredible views. Regardless of what you’re looking for, Monument Mountain has something to offer everyone who visits.

Monument Mountain is one of the best hikes in the Berkshires because it provides visitors with stunning views of the surrounding area.

In addition, the hike itself is not too challenging, making it perfect for all skill levels. And, if you’re up for a bit of a challenge, there are several options for more difficult trails leading off the main path.

The best time to visit Monument Mountain is in the fall when the leaves are changing color. However, it’s also a great spot in winter for snowshoeing or cross-country skiing. No matter when you visit, you’re sure to enjoy the incredible views. After you’ve worked up an appetite head only 5 minutes down the road to Great Barrington for a bite to eat!

5. Mount Greylock

Mount greylock - adams, ma

Mount Greylock is the highest point in Massachusetts and offers some of the most stunning views of any hike in New England. Even though it’s a bit of a “hike” from our house in New Marlborough, Mount Greylock is a must if you’re looking for challenging and rewarding hikes in Western Massachusetts.

As one of the best hiking Berkshires trails, the best time to hike Mt. Greylock is from late September to early October when the leaves are at their peak color.

The trail to the summit of Mount Greylock is relatively easy and can be completed by hikers of all skill levels. There are several different routes to the top, so you can choose one that best suits your abilities. Once you reach the summit, you’ll be rewarded with breathtaking views of the Berkshires.

If you’re looking for a challenge, Mount Greylock makes one of the best winter hikes in the Berkshires. The trail is more difficult in the snow, but the views are even more spectacular. No matter when you hike Mount Greylock, you’re sure to have an unforgettable experience.

6. The Mohawk Trail

mohawk trail

This trail is perfect for a day hike because it has something for everyone. The views from the top of this nice trail are incredible, and there are plenty of places to stop and rest along the way.

The trail is also very well-marked, so you won’t get lost. And, if you’re looking for a challenge, some steep sections will get your heart pumping. But don’t worry, there are also plenty of flat sections to catch your breath.

So whether you’re an experienced hiker or a beginner, The Mohawk Trail is the perfect hike.

7. Appalachian Trail

appalachian trail berkshires map

The famous Appalachian Trail winds through the heart of this scenic region. You can even pick up the Appalachian Trail from just a few minutes down the road, between our house and Great Barrington (on the right side of the Lake Buel Road if heading into town). The Appalachian Trail is one of the best hiking Berkshires have to offer for several reasons:

  • It is incredibly scenic, winding through forests and mountains with beautiful views at every turn.
  • It is relatively easy to follow, so you can relax and enjoy the hike without worrying about getting lost.
  • It is a great workout, offering both a physical and mental challenge.

So if you’re looking for a beautiful hike that ticks all the boxes, the Appalachian Trail is definitely worth checking out!

8. The Ashuwillticook Rail Trail

The Ashuwillticook Rail Trail

The Ashuwillticook Rail Trail is a ten-mile trail that goes through some of the most beautiful scenery in the Berkshires. The trail is perfect for all levels of hikers and even has a section for biking.

One of the best things about The Ashuwillticook Rail Trail is that it is open year-round. So whether you want to see the leaves changing color on one of the best fall hikes in the Berkshires or go on a winter hike and see the snow-covered landscape, you can do it all here!

Whether you are a local or just visiting the Berkshires, make sure to add The Ashuwillticook Rail Trail to your list of places to hike. It is truly one of the best day hikes in the Berkshires!

9. The October Mountain State Forest

The October Mountain State Forest

The October Mountain State Forest is one of the largest state forests in Massachusetts. Spanning more than 16,000 acres, the forest is a great place to hike, camp, fish, and hunt.

There are over 100 miles of scenic trails to explore in the October Mountain State Forest, so there’s something for everyone. Whether you’re looking for a short hike or a longer trek, you’ll be able to find what you’re looking for in the October Mountain State Forest.

A few things to keep in mind when hiking in the October Mountain State Forest:

  • Because there are so many different trails, it’s important to map your route before heading out.
  • Some trails can be quite challenging, so make sure you’re prepared for a hike that might take a few hours.
  • The October Mountain State Forest is home to abundant wildlife, so be aware of your surroundings and make noise while you hike to scare off the bears.

Honorable Mention: Questing

questing - new marlborough, ma hike

Less than 2 miles down the road from Oak Hill House you can find Questing, a relaxing nature preserve filled with remnant cellar holes, wetlands, and stone walls. Questing is a gorgeous 438-acre space, including a 17-acre wildflower field perfect for meandering through in spring. 

The Questing Reservation Loop is a relaxing 2.5-mile loop that’s great all year round. It’s not the most scenic hike, but it’s perfect for a quick walk to get out and enjoy the Berkshires.

Bottom Line

If you’re wondering what to do in the Berkshires a hike is always a good idea! There’s something for everyone, with a range of easy to difficult trails to choose from. And with spectacular views seemingly at every turn, you’ll soon want to return to this lovely corner of the Appalachians.

And if you’re looking for a cozy place to serve as your home base while hiking in the Berkshires we’d love to host you at Oak Hill House.