Our favorite hiking spots in the Berkshires | BIRCH Properties Blog

Our favorite hiking spots in the Berkshires | BIRCH Properties Blog

Looking to decompress and feel refreshed? The Berkshires has been a long-time popular vacation destination for just that purpose.  Known for outdoor activities, numerous lakes, fall foliage, and a hard-core farm-to-table food scene, the county also has many world renown arts institutions.  Dotted with charming historic villages, lakes, and towns, this western Massachusetts region is also beloved for its annual performing arts festivals, including the Boston Symphony Orchestra’s residency at Tanglewood Music Center in Lenox.

Though we are just 135 miles from New York City, geologically, our region is a subrange of the Appalachian Mountains.  If you are willing to go on a little adventure to explore some of the 209 named mountains here in The Berkshires, you will be rewarded for your efforts with some of the most incredible vistas you've ever seen.

Photo credit: Associate Broker & BIRCH Properties Agent, Samantha Homeyer

Whether you're just here for a season, or you've chosen to make the Berkshires your permanent home, we've listed a few areas to consider discovering.

Alander Mountain - Mount Washington, MA

See the blooming mountain laurel along the crest when you explore this Berkshires summit in late spring, early summer. With its breath-taking, 360-degree views, the Catskills are on full display atop Alander. Located at the border of New York and the southeastern corner of Massachusetts, this moderate-level journey will take you up an elevation gain of 1,200 feet, along 5.8 miles of trails. The first 2 miles are fairly flat and there is a picturesque little stream to navigate before continuing up the 650 feet of elevated climb. After about a mile there are some trails to the left, but to get to the top, stay on the path straight ahead!


Alford Springs - Alford, MA

With it's moderate to difficult terrain and its mostly forested ridgeline, it's best for seasoned hikers and mountain bikers, and in the winter it's especially noteworthy for more experienced snowshoers and backcountry Nordic skiers.  This spot has seven miles of trails throughout its 899 acres. Berry picking is also quite prominent here at Alford Springs where you can take in the gorgeous views of Alford Valley.


Ashintully Gardens - Tyringham, MA

With stunning views of Hop Brook Valley, this gentle excursion will bring you along footbridges and grassy terraces that link the gardens to a half-mile woodland trail to the ruins of what the locals called "Marble Palace" - a 35-room Georgian style mansion built in 1911 and destroyed by a forest-fire in 1952 that left behind only the foundations and four Doric columns that once spanned 13 bay windows. Ashintully Gardens (Gaelic for "on the brow of the hill") integrates natural features with sculptural elements and can be explored from sunrise to sunset, April 1 through November.  Dogs are not allowed at this site so, instead, take them to the neighboring McLennan Reservation for a hike through rugged and secluded landscape that was once part of the original estate.


Basin Pond - Lee, MA

These beautiful wetlands offer trails that cross a boulder field, which is perfect for your little ones to climb around on, exert some energy, and even play hide-n-seek along the way.  The 296 acres is excellent in the summer, offering 2.5 miles of trails and a wildlife viewing deck!  The difficulty level is moderate and it has some minor stream crossings where stones are available to step on, making it a skosh easier to forge your path forward to see the beaver pond and the site of long-gone man-made dams.


Bob's Way - Monterey, MA

This former heron rookery is a smaller hiking venue at 263 acres, and contains a multitude of loops along the 2.5 miles of trails.  Spring time is the favored season for taking this moderately difficult hike but you'll be happy to see the beaver ponds and other wildlife as you traverse the trails to get to the bedrock ledge, where there is impressive stonework and a special seat to take in the view.


Clam River - Sandisfield, MA

This leisurely and romantic summertime favorite is an easy place to explore.  With 550 acres and up to 6 miles of trails, the stream valley has a wild river, traces of a dam, extensive stone walls and foundations that soundlessly speak of a time when the millworks were bustling with activity.


Goodnow Preserve - New Marlborough, Ma

This adventurous exploration has about 300 acres of open fields, dense forest and woodland roads. The land varies in difficulty as you traverse down to the Konkapot River with downward slopes that are sometimes gentle and sometimes steep. There is also an old woods road about half a mile in distance to view the remnants of the Lower Carroll Mill.

Directions from the New Marlborough Land Trust state, "From the parking area, walk diagonally across the field, across the culvert and up along the edge of the field until you come to the second pasture. At the middle of the pasture, a trail to the right goes into the woods and leads to a hidden lower pasture; a trail to the left follows a stone wall to a pasture on Hadsell Street."  They have a printable PDF map on their website.


Hollow Fields - Richmond, MA

Spring is the perfect time to explore along the mowed paths in open fields with views that are both sunlit and nature-worn. These 660+ acres of moderate-level trails give you six miles for bird watching and perhaps a nice picnic!


Hoosac Range - North Adams, MA

If blueberry picking at Sunset Rock is on your list of summer activities, be sure to head to Hoosac Range, located on the Berkshire's northeastern side.  While autumn is a stunning time to take in the rock cliffs and dramatic vistas, the 989 acres of trails include up to 6+ miles of easy to difficult exploration that provides opportunity for snowshoeing along the ridgeline trail in the early spring.


Housatonic Flats - Great Barrington, MA

Dog-walking, bird-watching, and wild-life viewing are among the favorite spring activities at this 26 acre spot. The less-than-a-mile trail makes this an easy to explore the Housatonic Riverbank and spend time outside before heading to one of the art or history exhibits taking place throughout The Berkshires.


Mahanna Cobble - Lenox, MA

With 222 acres of difficult terrain, the northern trailhead for The High Road in the summer or fall is worth every one of the 3.2 miles trek to see the beautiful southern views once you reach the summit of Mahanna Cobble.


Photo credit: Associate Broker & BIRCH Properties Agent, Samantha Homeyer

Mount Hunger at Konkapot Ridge - Monterey, MA

As part of the Berkshire Wildlife Linkage, the moderately difficult, wooded ridgeline is only 1.4 miles round-trip - making it an excellent way to see what the 1,728 acres has to offer. The Mt. Hunger trail has interesting rock formations and provides gorgeous vistas of the historic homeland of the Mohican people.


Old Mill Trail - Dalton, MA

The best way to get to the upper reaches of the Housatonic River are via The Old Mill Trail. While the entire trail is 3 miles on the 127 acres of land, the accessible section with interpretive trails is about 1.4 miles.  Spring and summer are the best times to visit this area, and bring your pole!  Fishing is one of the favorite activities to do here.


Olivia's Overlook at Yokun Ridge South - Stockbridge, MA

At the center of the Yokun Ridge South reserve, and connecting to The High Road, lies Olivia's Overlook. The 734 acres spans Lenox, West Stockbridge, Stockbridge, and Richmond - with over 6 miles of moderately difficult trails! The views and Monks Pond are there to enjoy all year long but the mountain laurel and spring wildflowers are a must-see in season. Want to really immerse yourself in the famous New England foliage? Check out the overlook in the fall for an incredibly colorful experience!


October Mountain - Lee, MA

Inspired by the beautiful foliage and colors of these hills, writer Herman Melville named October Mountain as such due to the incredible view from his Pittsfield home. As the largest state forest in Massachusetts with 16,500 acres to explore, this state forest originated from the estate of William C. Whitney - President Grover Cleveland's Secretary of the Navy. There are trails for any experience level and the mountain boasts a campground with 44 designated campsites (and 3 accommodating yurts) available for visitors to reserve and enjoy between May and October.  Mountain biking, fishing, non-motorized boating, and cross-country skiing are just a few of the activities that are encouraged.

According to AllTrails, "One of the most scenic trails leads through Schermerhorn Gorge, a striking natural feature which has intrigued generations of geologists. Countless varieties of wild plants and animals can be found throughout the varied terrain of this vast forest."  Find a printable map of their 17 preferred trails here.


Parsons Marsh - Lenox, MA

Short and sweet, this accessible trail is only 0.6 miles round trip!  The 183 acres contains forested wetland and a quarry pond making it an exceptional habitat for birding, and is best explored during the spring, summer, and fall.


Steadman Pond at Konkapot Ridge - Tyringham, MA

The tranquil pond is excellent for swimming, bass fishing, bird watching, and perhaps a little picnic.  Though it sits on 790 acres, the easy trail is only a quarter mile - an easy summer find.


Steepletop - New Marlborough, MA

Though its name suggests a level of difficulty, the easy five miles of trails at Steepletop is especially good in the spring and winter, but ideal for year-round activities as well. The 1230 acres of expansive wetlands, and miles of woods that have a mixture of both mature and young forest growth, are managed for wildlife habitat.


Stevens Glen - Richmond, MA

We have just two words for Steven's Glen... Romantic Drama!  If you're looking for one of Berkshire County’s most impressive sights, the Lenox Mountain Brook cascading down the steep rocky ravine is sure to be it.  As a moderate level excursion, it takes about an hour to do this 1.2 mile trail, round-trip.  Sitting within 129 acres between Richmond and West Stockbridge, the waterfall, reflecting bench, and built-in viewing platform overlooking the deep hemlock forest make this a stunning, Berkshires Bucket-List item to explore.


The Boulders - Lanesborough, MA

Named for the historic boulders that are along the 6+ miles worth of trails, this 645 acres is easy to moderately difficult - depending on which trail you choose. Offering westward views of The Berkshires, that are especially good in the winter, spring, and fall, the beautiful tall trees, natural slides, and miles of trails are sure to help you decompress during your time here.


Thomas and Palmer Brook - Great Barrington, MA

Large sugar maples, interesting geology, and gorgeous views across the wetlands make this journey one for your trekking list. Though it spans 267 acres, there is an accessible section of trail that is half a mile long, and there are two miles of moderate trails that wind through an old pasture, wetlands, and a forest that culminates into a dramatic high point of exposed bedrock. This exploration is best enjoyed in the spring, summer, and fall.


Thousand Acres Swamp - New Marlborough, MA

As the main access point for Cookson State Forest, this property has an easy, dog-friendly flat trail that leads to a picnic area on Thousand Acres Swamp, and the unique Stebbins suspension footbridge over the Whiting River! You can choose from a variety of trails once you cross the bridge, including one that goes to the beautiful East Indies Pond and the foundations of old mills. This stretch of exploration is great for viewing wildlife, snowshoeing, and strolling along with your friends (furry or otherwise.) Get a printable map from the New Marlborough Land Trust here.


A special thanks to the Berkshire Nature Reserve Council and The Trustees of Reservation for gathering wonderful information on the best hiking spots in the area for us to share with you.

Photo credit: Associate Broker & BIRCH Properties Agent, Samantha Homeyer

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