Take a hike! Go for a walk, a swim, catch a fish, have a picnic, climb a mountain. We keep land so you can enjoy it.

Our top trails offer a range of activities. Find the one that is right for you…then try another one next time. Be sure to tell us how you liked it!

1. ALFORD SPRINGS, Alford
2. HOOSAC RANGE, North Adams
3. BASIN POND, Lee
4. STEVENS GLEN, West Stockbridge/Richmond
5. OLIVIA’S OVERLOOK AT YOKUN RIDGE SOUTH, Lenox/Richmond/Stockbridge/West Stockbridge
6. CLAM RIVER, Sandisfield
7. HOLLOW FIELDS, Richmond

8. BOB’S WAY, Monterey/Sandisfield
9. STEADMAN POND AT HUDSON-HOWARD, Monterey
10. HOUSATONIC FLATS, Great Barrington
11. STEEPLETOP, New Marlborough
12. PARSONS MARSH, Lenox
13. OLD MILL TRAIL, Hinsdale/Dalton
14. THE BOULDERS, Pittsfield/Dalton/Lanesborough 


TRAIL DIFFICULTY RATING KEY


1. Alford Springs, Alford

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hiking bird watching snowshoeing cross country skiing cycling berry picking geocaching picnicking photography  

Mother Loop: 2.4 miles; 1.5 hours
Father Loop: 4.3 miles; 2.5 hours
Difficulty: Walking, 3; Skiing, 4
Features: Blackberries in summer, noteworthy backcountry Nordic skiing in winter, with challenging ascents and descents. Gorgeous views of Alford Valley and beyond. Good hunting reported.
Especially good in: Winter
Directions/more information

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2. Hoosac Range, North Adams

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hiking snowshoeing bird watching photography picnicking 

Sunset Rock: 1.6 miles, 1.25 hours
Difficulty: 2
Spruce Hill: 6 miles round-trip; 4 hours
Difficulty: 3
Features: High elevation long views: prepare for the sublime! Cool rock cliffs formed by “glacial plucking” with trees twisted into fantastical forms by wind and ice. Blueberries at Sunset Rock and open ledges near Spruce Hill in summer. Awesome spring snowshoeing. Migratory raptors in fall, great viewing at Spruce Hill. Views over North Adams, Mount Greylock, and Florida State Forest.
Especially good in: Fall
Directions/more information

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3. Basin Pond, Lee

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hiking bird watching snowshoeing geocaching picnicking photography 

2.5 miles: 2 hours
Difficulty: 3 (easy walking, but does include a couple of stream crossings on step-stones)
Features: Beautiful wetlands, with a wildlife viewing deck in the sun. Trail crosses a boulder field which provides a great place for kids to climb and hide on trailside rocks.
Especially good in: Summer
Directions/more information

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4. Stevens Glen, West Stockbridge/Richmond

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hiking snowshoeing photography 

1.5 miles: 1.25 hours
Difficulty: 2
Features: 19th century tourist attraction, reborn for the 21st century including a waterfall through romantic rock cleft, stream to dabble feet on hot day, a viewing platform with bench for reflection. Deep hemlock forest also awaits.
Especially good in: Spring
Directions/more information

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5. Olivia’s Overlook at Yokun Ridge South, Lenox/Richmond/Stockbridge/West Stockbridge

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hiking snowshoeing photography picnicking cycling cross country skiing 

Note: Yokun Ridge South is the central hub of a multi-spoked trail network. There are multiple options extending north and south from there.

Charcoal Trail: 1.6 miles roundtrip, 1 hour
Difficulty: 3

Brothers Trail: 0.9 miles, 0.75 hours, one-way
Difficulty: 2

Burbank Trail: 3.2 miles roundtrip, 2 hours
Difficulty: 3

Old Baldhead Road to Monks Pond: 0.5 miles,  one-way, 0.25 hours
Difficulty: 2

Features: Charcoal pits (can you spot them?) and a run alongside Shadow Brook, named by Nathaniel Hawthorne. Remarkable stone work on trail itself. Also includes the tri-town monument: where Stockbridge, Lenox and Richmond meet…Berkshires’ answer to Four Corners.
Especially good in: Fall

Directions/more information for all Yokun Ridge South trails

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6. Clam River, Sandisfield

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 hikingfishing bird watching snowshoeing cross country skiing picnicking 

Clam River Loop Trail: 1.5 miles, 1 hour
Difficulty: 2

Clam River Trail: 3 miles roundtrip, 2 hours
Difficulty: 2

Hammertown Loop Trail: 1.6 miles, 1.5 hours
Difficulty: 2

Features: Beautiful, romantic stream valley, canyon-like in spots with access to Clam River. Old stone foundations and millworks along this cold water stream. Abundant wildlife.
Especially good in: Summer

Directions/more information

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7. Hollow Fields, Richmond

hiking bird watching snowshoeing cross country skiing picnicking photography 

2 miles round trip; 1 hour
Difficulty: 2

Features: Walk mowed paths through open fields – truly a rarity! Long views that are both sun-splashed and windswept, stunning in all seasons. Great bird watching, particularly in spring. Mellow spot for picnicking.
Especially good in: Spring
Directions/more information

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8. Bob’s Way, Monterey/Sandisfield

Bob's Way Berkshire Natural Resources Council

hiking bird watching cross country skiing picnicking 

2.5 miles; 1.5 hours
Difficulty: 2
Features: Multiple loops, so it’s easy to customize your walk with fabulous beaver pond views. Formerly a heron rookery, still teeming with wildlife. Dave’s Bench, a stone seat created from bedrock ledge and artisanal stonework sits atop with the best view of the house!
Especially good in: Spring
Directions/more information

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9. Steadman Pond at Hudson-Howard, Monterey

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 hikingcanoeing fishing swimming bird watching picnicking snowshoeing 

.25 miles; 10 minutes round trip
Difficulty: 1
Features: Pond in beautiful setting, excellent bass fishing. Swimming raft and rowboat await! Terrific bird watching. Great picnic and hangout spot.
Especially good in: Summer
Directions/more information

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10. Housatonic Flats, Great Barrington

hiking   bird watching picnicking snowshoeing 

1 mile; 30 minutes
Difficulty: 1
Features: Views of pastoral Housatonic River, birdwatching, dog walking. Super easy place to “air out” in a short time.
Especially good in: Spring
Directions/more information

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11. Steepletop, New Marlborough


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Louise Lane (North Loop): 2.2 miles, roundtrip, 1.5 hours

Edie’s Way (South Loop): 2.2 miles, roundtrip, 1.5 hours
Difficulty: 2
Features: Expansive wetlands, miles of wood road
Especially good in: Winter/Summer
Directions/more information 

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12. Parsons Marsh, Lenox

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Trail: 1/3 mile, one-way
Difficulty: 1
Features:  Marsh, forested wetland, and quarry pond
Especially good in: Spring/Summer/Fall
Directions/more information

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13. Old Mill Trail, Hinsdale/Dalton

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Accessible section: 1.4 miles roundtrip, 1 hour
Entire trail: 3 miles roundtrip, 2 hours
Features: accessible trail, fishing access, and interpretive trail
Especially good in: Spring
Directions/more information

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14. The Boulders, Pittsfield/Dalton/Lanesborough

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Healthy Heart Loop: 0.5 miles
Difficulty: 2

Green trail: 1.4 miles roundtrip, 1 hour
Difficulty: 2

Red trail: 2.4 miles roundtrip, 1.5 hours
Difficulty: 3

Blue trail: 2.8 miles roundtrip, 1.75 hours
Difficulty: 3

Features: Miles of excellent trails, beautiful tall trees, and the natural slides at The Boulders
Especially good in: Winter/Spring/Fall

Directions/more information

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Trail difficulty rating:
All time estimates are for walking in dry weather.

Difficulty ranges from 1 to 5
1- Accessible
2- Easy- Gentle grades, smooth footing
3- Moderate- uneven footing, elevation changes
4- Difficult- Strenuous due to length and/or terrain
5- Expert – No marked trails

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