The Best of the Berkshires: Hike Mt. Greylock, Massachusetts’ Highest Point
Greylock was my first “serious” solo hike years ago and I wasn’t impressed. I decided to give it another try, but this time, I took a different route and loved it. The best way to hike Mt. Greylock is on this 12-mile, 3,300 elevation gain traverse across Mt. Greylock, Stony Ledge, Mt. Fitch, and Mt. Williams.
Sunrise view of Mt. Greylock from my favorite vantage point of Massachusetts’ highest peak: Stony Ledge.
Greylock was my first, “serious” solo hike back in September 2017. I say serious because it was the first time I drove a bit of distance to hike roughly seven miles alone. It was something I always wanted to do, and figured by picking the highest point in Massachusetts, in September, with stretches on the loved Appalachian Trail, there would be other hikers on trail or visitors driving up Greylock Road if I needed something.
Looking back now, seven years later, it’s incredible to think back to how much I’ve changed in the outdoors since then. I thru-hiked for nine days in the most remote corner of the Adirondacks, hiked all 115 4,000 foot mountains in the Northeast, and even have five incredibly memorable days in the woods completing a handful of the Northeast Ultras.
One thing I never thought I’d see myself doing is trail running. As much as I love hiking and being outside, I thought my running would forever be limited to the road because I already trip going uphill while trekking. As with most things, I like to try everything once. Two years ago I found myself wanting to quicken my pace to reach a sunset atop a local summit (my favorite one in fact—Tekoa Mountain in Westfield, Massachusetts). I started trail running to not miss the sunset, and realized I kind of liked it. Since then, I’ve taken up trail running as much as I can get out on the trails and now have a trail running buddy who may love it even more than I do.
Despite always being willing to try things once, there are several things I would not repeat. Like hiking to the summit of Greylock. I haven’t revisited Massachusetts’ high point in years because the view from Greylock’s summit is underwhelming to me. A few years ago I discovered a new angle of Greylock that I absolutely love and have frequently found myself returning to—the view from the Stony Ledge overlook.
I decided to give Greylock another try, but this time, I wanted to add in my favorite view, and a few extra stops for more elevation gain. I ascended Stony Ledge, then summitted Mt. Greylock, followed up with Mt. Fitch and Mt. Williams for a wonderful stick season traverse. This might be one of my new favorite hikes in Massachusetts. Here’s the route and why it made it to my list of favorites:
1. Great training for more serious hikes (like the high peaks in the Adirondacks or the 4,000 footers in New Hampshire).
Greylock is the highest point in Massachusetts, and it still doesn’t quite compare in terms of feet to the peaks of the Adirondacks or the White Mountains. This loop, however, has 3,300 feet of elevation gain over 12 miles. It feels like a day up north without the long drive from Western Massachusetts.
2. Ample parking.
Since I went just days prior to the road up the mountain closing and I arrived prior to sunrise, there wasn’t a car in sight. The parking lot at the end of Hopper Road in Williamstown, MA is large enough for several cars and still had parking available when I returned around noon.
3. Well-worn and well-maintained trails.
As much as I love the Adirondacks for their grittiness and ruggedness, there is something about being able to trail run without obstructions consistently amidst your feet (and being able to look up occasionally to take in the view too).
The best way to hike Mt. Greylock and enjoy the best that the Berkshires have to offer is along the Mt. Greylock, Stony Ledge, Mt. Fitch, and Mt. Williams Traverse. There are plenty of other routes up to Greylock, much faster ones too, but this one truly has it all and it’s a loop. Win-win.
Here’s the route I took (and would definitely do again):
Starting Point: Haley Farm Trailhead at 1033 Hopper Rd, Williamstown, MA 01267
Hopper Road > Haley Farm Trail
The trail starts off nice and flat from Hopper Road. The first right turn takes you very swiftly up a steep incline up Haley Farm Trail. It’s roughly 1,500 feet of elevation gain in a mile and a half. I chose this route because I hoped to see the sun rise behind Mt. Greylock from Stony Ledge. It was a bit overcast, but I’m glad I conquered much of the morning’s gain in the first stretch. Though the Haley Farm Trail feels relentless at times, the view from the summit is totally worth it. There are a few overlooks with benches to rest at too. Racing the sunrise didn’t leave me much room to relax. I pushed through to the summit and spent some time soaking it in. Stony Ledge has a picnic table at the top too, making it an ideal hike at any time of day.
After enjoying a cloudy sunrise, I continued on Sperry Road. This one’s another favorite! There are several campsites and bear-proof food storage lockers at each site that you pass along the way that I continuously remind myself I need to return to one day for an overnight. The Sperry Road Campground located within Mt. Greylock State Reservation is currently closed for renovations and off-season now at the end of 2024. It reopens mid-May to October and is hike-in only. Definitely on my list to camp at one of these days!
Sperry Road > Hopper Trail
Time for the real gem of this hike – the Hopper Trail. There are a few access points to it, but I continued on Sperry Road until where the Campground Trail interests with Sperry Road and the Hopper Trail. I took a left on the Hopper Trail then, and continued upward. This is where I saw the first hiker of the day. The Hopper Trail continues until you come to a split with the Overlook Trail.
Overlook Trail > Appalachian Trail > Summit
I veered right, though you could go left for a bit to see Mt. Greylock from a different vantage point. I knew I had a long day, so I headed straight to the summit. The Overlook Trail merges with the Appalachian Trail heading north. Soon there is a small pond on the left of the trail. The pond has a small cabin that in years past hikers could walk into. As of November 2024, the trail to the cabin is closed for restoration purposes. The pond is a great landmark for being near the summit.
Just after the pond’s serene views is the road intersection of Notch Road and Summit Road. Continue on north along the Appalachian Trail to the iconic, 92-foot granite tower atop the summit of Mt. Greylock.
I walked up to the Veterans War Memorial Tower, only to find the doors locked. I figured it was due to heavy winds that morning, but just as I turned around, a Mount Greylock State Reservation employee approached the door and unlocked it. I made my way around the spiral staircase to the top. I had endless views of Vermont, the Catskills and the serene Berkshires all to myself for a few minutes. After seven years and a few hikes at this summit, I finally experienced the hype of Greylock. I headed down as others made their way up the tower, and onward to my next peak.
Appalachian Trail > Money Brook Trail
This stretch of trail might’ve been my favorite of the morning. I barely saw a soul, hiked up and over Mt. Fitch and Mt. Williams, and passed by a neat campsite at Wilbur Clearing. The privy even had AT carving into it. I took a detour to Money Brook Falls. With a totally sunny October without rain, the falls weren’t rushing.
Money Brook Trail > Hopper Road Parking Lot
After the detour to the falls, I continued pack downhill on the trail. The trail follows the brook for almost the entirety of the route back to the car. Fall foliage was gone by the end of October up at the summit of Greylock, but a few leaves remained along the Money Brook Trail.
End Point: Haley Farm Trailhead at 1033 Hopper Rd, Williamstown, MA 01267
This route definitely changed my mind about Mt. Greylock. A quiet, late autumn morning on a longer traverse made me love this state’s high point.
Have you hiked Mt. Greylock? If you enjoyed learning about this route, then you may enjoy these hikes around the Northeast:
Hike the Vermont 5 4,000 Footers
Lake Placid 9er Hiking Challenge
Twins Zealand Bonds Traverse (part of the NH 48 Challenge)
Tupper Lake Triad Ultra: The Best Beginner Hiking Challenge for Dogs
I decided I wanted to complete Tupper Lake Triad in a day with my dog— three hikes totaling 7.4 miles and 1,975 feet of climbing. Here’s everything you need to know for a Tupper Lake Triad Ultra:
Lake views from the fire tower atop Mt. Arab on an October morning.
After finishing the Northeast 115, I wasn’t drawn to any particular hiking challenge. Once leaves began to change, so did my feelings toward a new goal. I set my sights on a trio of trails that I could do with my favorite hiking partner, Poppy. Poppy spent the summer hitting the trails with me and seemed ready for a bigger day.
Despite her love for the trails, she hasn’t hiked any 4,000-footers. Yet. She earned her trail legs last month in October when we headed up to Tupper Lake in New York to take on the Tupper Lake Triad—a list of three summits in the scenic town of Tupper Lake comprised of: Mt. Arab, Goodman Mountain, and Coney Mountain. A trip to Tupper Lake could include one of these alone and it would be a wonderful time spent outside. However, I wanted to tackle all three in a day to complete the Tupper Lake Triad Ultra – something Poppy and I could do together. In a day, these three hikes total 7.4 miles and 1,975 feet of climbing. If you subtract the short drives in-between, it almost feels like a 4,000 footer. Great practice for my trail buddy!
Everything you need to know for a Tupper Lake Triad Ultra:
1. Mt. Arab (2,525 feet)
Location: Mt Arab Rd, Tupper Lake, NY 12986 (Mt. Arab Trailhead & Parking)
Distance and elevation: 2.1 miles out-and-back, 768 ft gain
Parking: Plenty of parking with multiple spots opening up both when we arrived and when we left at the Mount Arab Trailhead Parking.
Trail: Take the Mount Arab trail up to the summit, and back down.
Mt. Arab was my favorite of the three mountains mostly because I’m a sucker for a fire tower. I love seeing expansive views, and it’s almost a guarantee when it comes to an Adirondack fire tower (weather permitting, of course).
2. Goodman Mountain (2,190 feet)
Location: Adirondack Park Preserve, Tupper Lake, NY 12986 (Goodman Mountain Trailhead)
Distance and elevation: 3.1 miles out-and-back, 607 ft gain
Parking: Plenty of parking at the Goodman Mountain Trailhead, and with the hike being so short, multiple spots opened up in the time we arrived and departed.
Trail: Take the Goodman Mountain trail up to the summit, and back down.
Excellent views from the summit of Goodman Mountain.
3. Coney Mountain (2,264 feet)
Location: NY-30, Tupper Lake, NY 12986 (Coney Mountain Trailhead)
Distance and elevation: 2.2 miles out-and-back, 600 ft gain
Parking: There are only one or two spots at the Coney Mountain parking area. Parking is available on the very busy road, but the spots are endless.
Trail: Take the Coney Mountain trail up to the summit, and back down.
Receiving your Completion Patch
Once you complete all three (in a day or over multiple days), submit your registration to the Regional Office of Sustainable Tourism with $5 for a patch for you and your pup. The Tupper Lake Triad challenge offers online registration. My patch arrived in my mailbox within a week!
Preparing Your Pup
I trained Poppy on local trails prior to tackling the high elevation gain of all three hikes in one day. A big advantage of the Tupper Lake Triad is that although the elevation gain mirrors an Adirondack 46er, the trails are very well-maintained and accessible. Driving from trailhead to trailhead gave her a chance to recover before the next hike.
Affordable Lodging Near Tupper Lake, NY
Since Tupper Lake is roughly a four-hour drive away from home, I opted to camp at a nearby state campground—Fish Creek Pond. This campground has plenty of sites, bathrooms, and views.
I wanted to test out an air mattress in the back of my SUV, so we car camped at Fish Creek. Definitely worth it!
Where to Eat in Tupper Lake, NY
In this area of the Adirondacks, I always gravitate to Raquette River Brewing. They truly have it all: a plethora of food trucks, beers, and parking spots.
Is the Tupper Lake Triad (ultra or not) making it onto your hiking list? If you enjoyed learning about this hiking challenge then you’ll love exploring these:
Hike the Vermont 5 4,000 Footers
Lake Placid 9er Hiking Challenge
Twins Zealand Bonds Traverse (part of the NH 48 Challenge)
The Best Local Hike in Western Massachusetts
Everything you need to know about the best local gem hike in Western Mass…
Tekoa’s rocky ledge viewpoint is Western Massachusetts’ best-kept secret. Read on to find out how to get here.
One of the top reasons on my list for wanting to move to Western Massachusetts was for the outdoor adventuring. Growing up in a suburb of Dallas, hiking looked like going to local park and exploring the woods. It was a great way to pass a Saturday afternoon (and who can complain about time spent outdoors/), but I craved more. I wanted longer trails. Elevation gain. Summit views.
Western Mass has this hidden beauty that only those who visit will ever uncover. Most people who visit Massachusetts frequent Boston or the Cape. There’s a running joke up here that Worcester is Western Massachusetts to Bostonians. Very few take the scenic drive out to what I consider to be the real gem of the state.
I may be biased, but Western Mass has it all—from outdoorsy adventures to breweries, to easy access to day trips. In the six years I have resided here, I frequent many of the same trails. In the last year, however, I discovered countless new ones. My all-time favorite? Tekoa Mountain. And here’s why.
Tekoa is something special.
It’s not easily accessible. It’s not a walk in the woods like many Western Mass favorites. It’s immersed in nature. Untouched, it feels like. Overgrown at times. Rarely do I see other hikers on this mountain despite its beauty.
I first stumbled upon it on a solo drive to upstate New York. Everyone driving to that area of New York on the Mass Pike crosses over a bridge that showcases encompassing valley views. Yes, that bridge you see way down there in the images above.
If you’re able to glance long enough, you notice a rocky ledge on the upper righthand side. After I caught sight of it for the first time, I made a mental note of the town I was driving through (Russell, MA), and researched it as soon as I could. Want to know what I found?
Nothing.
No trail maps, no trail reviews—nothing on AllTrails, and that says something.
I found a few comments about a steep route up that involved a sketchy parking situation that I was not keen on venturing into. I put off the search for a couple years and decided to try again last fall. I lucked out after some digging and found a legal parking spot. With a little trial, some error, and a sprinkle of wrong turns, I finally found my favorite outdoor gem in Western Massachusetts and it sure was worth the wait.
Everything you need to know about hiking to the ledge atop Tekoa Mountain:
Parking – This is the trickiest part. The safest parking I found is along a residential road that ends with a gate that the town needs access to. There is room for about five cars to avoid blocking the gate. I plug in 48 Reservoir Road, Westfield, MA into Google Maps. This is technically in the town of Montgomery, but it will show up as Westfield. Once you’re on this quiet road, drive to the end. Park there. Again, be sure to not block the gate.
Cost – Free!
Distance – About 5 miles out-and-back with a little over 1,000 feet elevation gain. There is an option to make a loop at the summit for a sunset view and different vantage point of the valley (with a little bushwhacking involved). If I could do it as a beginner bushwhacker, so can you! Sunset technically can’t be seen from the ledge, so this loop is great if you want that sunbeam shining through.
Difficulty – The reason this hike is my absolute favorite (and a Western Massachusetts hidden gem) is because most people think they need to travel a far distance for a tougher hike. I was one of those people, so I totally get it. What I love about this hike is that it’s local, peaceful, and has a climb. I love those short, easy hikes as much as the next hiker, but there’s something to be said for putting in the work and getting the payout once you reach the summit.
The route I take (logged on Strava) is above. From the parking to the viewpoint as an out-and-back.
Trail Details – After parking on Reservoir Road, follow the road behind the gate for a little under half a mile. It’s a steady, slight climb on a wide, gravel road. Veer left at the half mile mark and you’ll approach a gorgeous view atop a bridge of the Tekoa Reservoir. The calming stream and serene surroundings provides a great opportunity to catch your breath and enjoy the scenery.
When you’re ready, continue onwards and upwards. You’ll reach a Y intersection. Take the right, even though there’s a very official-looking sign on the left (it’s an informational sign). It’s not the direction you want for this hike.
Coming up is one of the best parts of this hike: the climb. After you turn right, you’ll follow along Moose Meadow Brook until you’re about a mile in. Here’s where I’ve gone astray far too many times. As you approach a mile, keep your eyes peeled for a left turn off the road into a dirt trail. It’s easy to miss if you’re deep in conversation, trail running, or just enjoying your hike. You’ll know you went too far if you cross another scenic bridge at a mile in. This bridge is great, but it means you missed the turn.
Once you’re in the woods, a gorgeous, well-trekked walk along a stream before the climb kicks in around a mile and a half in awaits you. This is one of my favorite parts of this hike because I have yet to come across anyone on this trail. It’s just the sound of the stream, the chirping of birds, and me. And my thoughts of bear encounters flooding in, of course. The first big climb of the hike flattens out for a tenth of a mile before beginning the final ascent to the ridgeline. Continue following the yellow markers. Though I usually see chipmunks or squirrels on this hike, I saw a bear for the first time here in May.
Tekoa in Winter
After one lovely dumping of snow, I knew I had to get out on the trail up Tekoa. It definitely did not disappoint. Snowshoes would have been a smart choice considering how infrequently traversed this trail is.
Depending on the season, the trail here is not maintained well. Be sure to bring bug spray or wear long pants to avoid any fun bug or plant reactions.
Once you finish that second, steep climb, you will find your trail opens up like a T. There are red markers here to remind you to take this trail back. Take a left and follow the yellow markers until you reach the summit. There are a few rolling hills and some rusty car parts along the way.
The viewpoint is approached from a wide clearing at the top with distant views of Springfield to your left. Take the trail to the right of the rock pile to reach the iconic, rocky ledge view you may have seen from the Mass Pike.
As always, please leave no trace. Whatever you bring onto the hike, please take back out with you to ensure this local gem stays beautiful for everyone.
You really cannot go wrong with any season you choose to accomplish this hike in. From foliage in the fall, to snow-capped hills in the winter, to the luscious greenery of spring — the constancy of a great view remains unchanged.
Tip: This is an incredible spot for sunset, and though the trail itself is not maintained well in terms of overgrowth, the trail markers have reflective stickers on them. For someone who is easily distracted in nature, I found these stickers so helpful with my headlamp even while trail running post-sunset.
What makes your favorite hike your favorite? Are you adding Tekoa to your list of must do hikes in Massachusetts? I’d love to know!
If you’re looking for more New England hikes and gems, you’ll enjoy:
4 Tips for Taking the Best Foliage Photos in New England
In the last five autumns I’ve spent chasing the foliage in New England and upstate New York, I’ve come up with a handful of tips through…
When I moved to New England, I didn’t know what I was getting myself into with seasons. In Texas, we’re either in summer or a chillier version of summer. What I wasn’t ready for is just how stunning fall can be. Contrastly, it can also be very difficult to decipher how to photograph such beautiful scenes.
In the last five autumns I’ve spent chasing the foliage in New England and upstate New York, I’ve come up with a handful of tips through long drives, failed hikes, and hidden gems of how to find the best photos of foliage. My pictures below are from the Adirondacks, which isn’t technically New England as it’s in New York, but given the proximity to the other mountains I frequent, the foliage timing and tips are very similar.
Here are my tips for how to take the best fall foliage photos in the Northeast:
1. If the weather is gloomy, it’s still worth making the trip.
The rain stopped when I reached the summit of Baxter Mountain and the clouds were sweeping through the layers and layers of mountains.
I used to only hike in what I considered ideal weather conditions. It had to be a sunny or clear sky, or absolutely no chance of rain. You wouldn’t catch me hiking in the rain. Wet socks, potentially wet camera gear – not my idea of a good time.
Last weekend, I was eager to get back to the Adirondacks. The only setback was a 100% chance of showers from when I arrived late Friday night to when I was leaving Sunday afternoon. I could’ve canceled. I could’ve stayed in western Massachusetts and shifted gears.
Instead, north I drove. Rainy weather has a unique way of bringing out foliage. It’s the weather of autumn and I’m embracing it this year, instead of turning away from it. Rain brings moodiness to the mountains with low moving clouds. I’m gravitating more toward this moodiness over bluebird days because you can’t plan for this scenery. It just happens because you went out and took a chance.
A cloudy day when the clouds break to let the sunlight in makes for one of my favorite views.
2. Hike lower elevations.
You don’t need to pick a 16-mile, 2,000 foot elevation gain hike to see the foliage. A drive through Lake Placid will easily give you the fall vibes! I highly recommend finding short hikes in the area you want to explore. Often times, they may not be as popular as most people are chasing a hiking list of the high peaks.
If you’re looking at the White Mountains, find a hike in the Lakes region or a less popular hike like Welch and Dickey. Shorter hikes often have parking more available as hikers head in and out at a faster pace. If you’re looking at the Adirondacks, the Lake Placid 9 (9 peaks around Lake Placid) are definitely worthwhile.
When I say hike low, I mean you don’t need to aim for 4,000 footers. Unless you want to! I decided to chase the foliage this year, and not the high peaks for autumn views.
Aerial views provided by reaching the summit of Baxter Mountain.
Don’t be fooled at these lower elevation hikes. The gain is still sweat-breaking! On some of the Lake Placid 9 hikes, you’re gaining 700-800 feet in a mile. Impressive for a 2-3 mile roundtrip hike.
Incredible views after a short hike up Mt. Van Hoevenberg.
3. Pull over when you see a worthwhile view.
There are so many incredible spots around the mountains to pull over safely and snap a photo. Think: rivers, trees, and small towns. Two weekends ago, as I was driving from Lake Placid to Wilmington, I saw a fishing spot that looked scenic.
A beautiful view of Whiteface Mountain from a parking spot at a fishing spot.
I pulled over next to a few fishermen, headed down the bank, and snapped a few shots of falls with foliage galore.
Lake Placid added a new lookout point along Mirror Lake. I stopped when I saw this view while driving by.
4. Don’t expect the perfect shot.
Most photographers edit their photos with fancy programs, so don’t go in thinking you’ll have an incredible aerial view of a mountain lake from a summit. Professional photographers are very good at their jobs – and editing is part of that!
The weather during fall is also very unpredictable. Even if the forecast calls for clouds, you may end up with constant downpour. If it calls for rain, you might get sunburnt because the sun will come out. You never know what you’re going to get – so get out there and be prepared!
Autumn is the perfect season for those moody mountain pictures. In these last couple trips, I’m more and more welcoming of clouds and rainy weather!
A rainy day led to an opening of the skies at the summit of Big Crow mountain.
Last weekend, I planned to call it quits early because of the nonstop rain. Instead, I tied my laces and headed up one of the Lake Placid 9 in Keene, New York. The rain had miraculously ceased and from the skies the clouds parted. I was enamored with foliage views for miles. And mountains immersed in the clouds. Had I just headed home early, I would’ve missed this view.
It wasn’t planned. It wasn’t the view I had seen when researching this hike. To me, it’s the perfect shot to remember the awesome feeling of a new experience hiking solo in new places.
Do you go leaf peeping? What tips would you offer someone trying to see all that foliage has to offer?