Cheshire Cobbles Hike: Trail Guide & Turn-by-Turn Directions
The Cheshire Cobbles hike in Massachusetts offers amazing views plus unique rock formations on the way up all for a short (but steep!) hike along a section of the Appalachian Trail. 🥾
In this post, I tell you everything you need to know to hike Cheshire Cobbles aka The Cobbles. The route I made and share with you has a waterfall right at the start of the hike (the route you find on AllTrails does not!).
Learn where to park, trail details, and turn-by-turn trail directions to help you find your way! ☺️
Living in the Berkshires for several years, I’ve learned there are so many great hikes all across the Berkshires to choose from.
I’ve done this hike multiple times in both summer and fall and to me it stands out as a hike with exceptional views for just a little bit of work – it’s a great workout!
The Cheshire Cobbles hike is located in the northern Berkshire town of Cheshire, just south of Mount Greylock – which you’ll be able to spot in the distance on this hike!
I haven’t explored much of downtown Cheshire but I’ve driven here plenty for its outdoor attractions like the Cobbles hike and for walks on the Ashuwillticook Rail Trail. Since the Appalachian Trail runs through downtown Cheshire – don’t be surprised if you see people with big backpacks (thru-hikers) walking along the street. 🙂
While there is a 3-mile route to the Cheshire Cobbles on AllTrails, it’s not clear where to park and it also brings you beyond the view (which we tried doing) – but it ends at a random point in the woods with no other view.
That’s why I made my own route and map on AllTrails to share with you (linked in the info box below). With my route, the parking is clear (large lot on Notch Rd.) AND, you get a bonus waterfall at the very start of the hike!
The Cascades waterfall (Formerly known as Cascades on South Brook) is perfect for allowing the dogs to get a drink before or at the end of the hike. We used it as a cool-down spot after our hike at the end of July.
It felt great to take the boots off and step in! 🌊 Now let’s get to all the info you need to start your journey…
🥾Cheshire Cobbles Hike Details 🥾
- Miles: 1.55 miles
- Elevation: 584 ft elevation gain
- Level: Moderate – Difficult (short but steep hike! nothing technical, no big scrambles)
- AllTrails link 🔗
- Trail Type: Out & back
- Average Time: ~1 hour
- Parking: Click here to navigate to 42.55602, -73.14462; a small gravel lot on Notch Rd. with room for ~8 cars
- Dog-friendly: yes, this is a steep trail but no big jump ups or downs for dogs
- Trail Highlights: Wide open view facing northwest, spot Mount Greylock and Cheshire Lake in the distance!
🗺️ TURN-BY-TURN TRAIL DIRECTIONS 🧭
1.) Walk to the western corner of the parking lot towards the medium-sized rocks.
Find the start of the trail and you’ll notice the waterfall immediately down on the right.
2.) At 0.16 miles, you’ll notice a trail off to the right, continue straight on the wide path.
3.) At 0.3 miles, you’ll notice the ‘Welcome to the Appalachian National Scenic Trail’ sign on the tree to the right along with a yellow no hunting sign.
4.) The trail continues up to the left where the incline begins!
5.) At 0.4 miles, you’ll start to notice yellow markers on the trees to the left.
6.) At 0.48 miles, reach the juncture with the white blazed Appalachian Trail, turn left here.
7.) At 0.66 miles, you’ll notice the large rockfall on the left, continue straight on the white blazed AT trail.
8.) At 0.72 miles, turn left at the ‘Cheshire Cobble Viewpoint’ sign onto the blue trail.
9.) At 0.75 miles, arrive at the view and see the sign ‘The Woods’. Arrived at the start of the view, keep walking to the final and best viewpoint at 0.77 miles.
10.) Return back the way you came!
11.) At the 1 mile mark, stay to the right when you see the Notch Road parking sign. Reminder: do not continue along the Appalachian Trail. 🙂
That’s it, friends! At this point you are done with the hike and are safely back at your car. 🙂 Below I have additional information about the Cobbles and the town of Cheshire if you’re interested in reading more!
And if you’re looking for more hikes in the area check out my post ➡️ 13 Best Hikes in the Berkshires!
OR, if you’d like to take on that big boy you see in the distance from the view here (Mount Greylock ⛰️) then check out my post ➡️ 4 Routes Up Mount Greylock! And choose the one that’s best for you. 🙂
Other Outdoor Attractions in Cheshire, MA:
Cheshire serves as a gateway to a host of picturesque mountains. The town’s designation as an official Appalachian Trail Community reflects its commitment to supporting hikers and preserving the natural beauty of the area. Local businesses participate in the Appalachian Trail Community Supporter program, providing essential services and support for hikers.
-Mount Greylock
Mount Greylock is the highest peak in Massachusetts. Accessible via the Cheshire Harbor Trail, this mountain offers a challenging yet rewarding ascent for hikers. At the summit, the War Memorial Tower stands as a tribute to the area’s rich history and provides panoramic views that are simply breathtaking.
The Mount Greylock Visitor Center is open year-round, offering recreational information and exhibits that enrich the visitor experience. Whether you’re visiting in summer or fall, the summit road typically opens between late May and mid-November, allowing easy access to the peak and its stunning vistas.
-Ashuwillticook Rail Trail
The Ashuwillticook Rail Trail offers another fantastic option for outdoor enthusiasts. This 12.7-mile trail follows the route of an old railway, providing a flat and accessible surface suitable for all ages and skill levels. Perfect for biking, running, or walking, the trail caters to a wide range of activities and provides a scenic journey through the Massachusetts countryside.The trail’s accessibility and gentle terrain make it a popular choice for families and casual hikers. As you traverse the Ashuwillticook Rail Trail, you’ll be treated to beautiful views and a tranquil environment, making it a perfect complement to the more challenging hikes in the area.
Frequently Asked Questions
What is the best time to hike Cheshire Cobbles?
Sometimes the best scenery and temperatures are in the fall. But the Cheshire Cobbles trails are open year-round! Because it is steep I suggest going early in the morning if you’re hiking in the summer before it gets too hot.
Are there any notable landmarks on the Cheshire Cobbles trail?
Absolutely! One of the highlights along the Cheshire Cobbles trail is a small but beautiful waterfall along South Brook. It’s a lovely spot for you and the dogs to cool off.
Is the trail suitable for beginners?
Yes, the Cheshire Cobbles trail is suitable for beginners, as it’s under 2 miles long. It is a challenging trail in that it’s steep, but there is no technical climbing here, just a great workout!
What wildlife can I expect to see on the trail?
On the Cheshire Cobble trail, you can expect to see white-tailed deer and wild turkeys. It’s a great chance to connect with nature!
Are there any nearby attractions worth visiting?
You can drive up to Mount Greylock, the highest peak in Massachusetts, or if you have more energy – try biking or walking along the Ashuwillticook Rail Trail.
I hope you enjoyed this post all about hiking the Cheshire Cobbles! Feel free to leave any questions below. 🙂
