In the high country of western Massachusetts, tucked under the hush of beech groves and the sprawl of maples, October Mountain rises like a quiet thought. The name itself—borrowed from Herman Melville, who could see the slope from his study in Pittsfield—carries a hush of color and seclusion. Here, in towns like Tyringham and Washington, time doesn’t stop, but it certainly strolls. This isn’t the Berkshires you pass through—it’s the part you disappear into.
The region is all folded hills, gravel roads, and forest silence, where towns press softly into the woods like they’ve been trying not to disturb anything since the 1800s. Each village—whether it’s Monterey with its old colonial bones and glassy Lake Garfield, or Savoy with its waterfalls and highland hush—offers a different kind of escape. But what they share is the absence of hurry, the presence of place.
October Mountain, the largest state forest in Massachusetts, wraps these towns in green silence for much of the year, until the leaves blaze into their namesake riot. If you’re chasing stillness, trout streams, starlight, or the ghost of Melville’s whale, this is the place to lose the signal—and find something better.
10. Monterey: Hidden Away in Nature’s Embrace
Monterey, with a population of around 1,000 residents, is a tranquil town nestled in the southern Berkshires. Known for its abundant forests and serene Lake Garfield, it’s a haven for outdoor enthusiasts who enjoy hiking, fishing, and boating.
The town’s primary industries revolve around tourism and small-scale agriculture, contributing to its quiet, rural character. What makes Monterey particularly secluded is its low housing density and the vast stretches of protected land that surround it, including Beartown State Forest.
The town’s winding roads and lush woodlands create a natural barrier from the busier neighboring areas, offering residents and visitors a peaceful retreat. Hidden gems like the Bidwell House Museum, a colonial homestead, add to Monterey’s quaint charm and sense of timelessness.
Where is Monterey?
Located in southwestern Massachusetts, Monterey sits near the New York state border, tucked away in the rolling hills of the Berkshires. Its seclusion is enhanced by its distance from major highways, with Route 23 being the main road connecting it to other towns.
The surrounding forests and lack of urban development make it feel remote, despite being just a short drive from Great Barrington and Lee. Visitors can reach Monterey by taking the Mass Pike (I-90) to Exit 2 and then winding through scenic country roads, making the journey part of the tranquil experience.
9. New Marlborough: Countryside Peace and Privacy
New Marlborough, home to approximately 1,500 people, offers a serene escape amid the Berkshire Hills. The town’s expansive rural landscapes are dotted with farms, meadows, and pristine woodlands, making it ideal for outdoor activities like hiking and bird watching.
Agriculture and small businesses form the backbone of the local economy, reinforcing its pastoral ambiance. The seclusion of New Marlborough is evident in its spacious properties and minimal commercial development, providing residents with ample privacy and a strong connection to nature.
Hidden treasures like Campbell Falls and scenic roads lead to charming villages within the town, each with their own unique character and history.
Where is New Marlborough?
Nestled in southwestern Massachusetts, New Marlborough is bordered by several other small towns, enhancing its tucked-away feel. Its location away from major highways contributes to its tranquility, with the nearest significant roadway being Route 7, several miles to the west.
The town’s five villages are connected by quiet, winding roads that meander through the countryside. To get there, travelers can take Route 57 or Route 183, both of which provide scenic drives through the heart of the Berkshires, making New Marlborough a peaceful destination off the beaten path.
8. Tyringham: Quaint Valley Seclusion
Tyringham, with a small population of around 300 residents, is a picturesque town nestled in a quiet valley of the Berkshires.
Its idyllic setting is perfect for those looking to immerse themselves in nature, offering activities like hiking the Appalachian Trail and exploring the stunning Tyringham Cobble, a unique geological formation.
The town doesn’t rely on significant industry, which helps maintain its peaceful, rural atmosphere. Tyringham’s seclusion stems from its ample undeveloped land, low population density, and absence of commercial zones, creating a sanctuary away from modern distractions.
Visitors often marvel at the charming Union Church and the whimsical Santarella Gingerbread House, which add to the town’s unique allure.
Where is Tyringham?
Located in central Berkshire County, Tyringham is tucked between Beartown State Forest and the Mountain Pasture Preserve, further enhancing its sense of isolation. The town is off the main tourist routes, with the nearest major road being the Massachusetts Turnpike (I-90), accessible via small, scenic roads.
The surrounding hills and protected lands act as natural barriers, preserving the town’s tranquility. To reach Tyringham, visitors often enjoy the leisurely drive along Route 102 and then weave through serene backroads, making the journey as peaceful as the destination itself.
7. Otis: Wooded Retreats and Quiet Roads
Otis, a town of about 1,600 residents, is a woodland haven in the southern Berkshires. Renowned for its vast forests and serene lakes like Otis Reservoir, the largest body of water in Massachusetts’ western region, it offers ample opportunities for boating, fishing, and hiking.
The local economy centers around tourism, particularly during the summer months, and small-scale retail that caters to visitors and locals alike. Otis’s seclusion is characterized by its extensive woodlands, spacious properties, and the quiet roads that wind through the countryside.
The town’s commitment to preserving its natural environment adds to its appeal as a private retreat. Hidden gems include the Knox Trail, a route used by Henry Knox during the Revolutionary War, which history enthusiasts can explore.
Where is Otis?
Situated in southwestern Massachusetts, Otis is bordered by several other small towns, enhancing its secluded setting. Its distance from major highways, with the Mass Pike (I-90) being the closest but still a drive away, keeps traffic minimal.
Surrounded by state forests and conservation areas, Otis feels far removed from urban centers. Travelers can reach Otis by taking Route 23 or Route 8, enjoying scenic views along the way. The journey through the Berkshire landscapes to Otis is as much a part of the experience as the destination itself.
6. Hinsdale: Quiet Shores of Plunkett Lake
Hinsdale, with a population close to 2,000, is a peaceful town nestled amidst the Berkshire hills. The town is known for Plunkett Lake and Lake Ashmere, which provide tranquil settings for swimming, fishing, and kayaking.
The local economy includes small businesses and seasonal tourism, particularly catering to those seeking lakeside leisure. Hinsdale’s seclusion comes from its expansive properties, the dense forests that envelop the town, and its distance from the region’s busier areas.
Quiet neighborhoods and limited commercial development make it an ideal spot for a secluded lakeside lifestyle. The Old Mill Trail, offering picturesque walks along the East Branch of the Housatonic River, is a favorite among locals and a hidden gem for visitors.
Where is Hinsdale?
Located in central Berkshire County, Hinsdale is surrounded by natural beauty and is somewhat removed from the main thoroughfares. The town sits to the east of Pittsfield, the county’s largest city, but maintains a distinctly rural feel due to the surrounding woodlands and water bodies.
The nearest major roads are Routes 8 and 9, which connect Hinsdale to neighboring towns while preserving its quiet atmosphere. Visitors can reach Hinsdale by meandering through scenic routes that showcase the best of the Berkshires, ensuring a peaceful journey to this serene lakeside community.
5. Savoy: Seclusion Amidst Scenic Trails
Savoy, home to around 700 residents, is a tranquil town known for its natural beauty and extensive network of hiking trails. Encompassing parts of the Savoy Mountain State Forest, the town offers numerous outdoor activities like hiking, snowmobiling, and cross-country skiing.
There is little in the way of industry apart from logging and small-scale agriculture, which underscores its rural charm. Savoy’s seclusion is heightened by natural barriers such as mountains and forests, and minimal development keeps it off the beaten path.
The town’s hidden treasures include Tannery Falls and Parker Brook Falls, cascading waterfalls tucked away in the lush forest that attract nature lovers seeking solitude.
Where is Savoy?
Positioned in northeastern Berkshire County, Savoy is nestled in the Berkshire Plateau, contributing to its remote ambiance. Away from major highways, the town is accessible primarily via Route 116, a scenic route that winds through the highlands.
The combination of elevation and dense forests separates Savoy from more populated areas. Travelers seeking a quiet escape will find the journey to Savoy filled with panoramic views and peaceful landscapes, making it a secluded destination well worth the drive.
4. Windsor: Rural Landscapes and Rolling Fields
Windsor, with a population of approximately 900, is a quintessential rural New England town characterized by open fields, rolling hills, and dense woodlands. Outdoor activities abound, including hiking at Notchview Reservation, a haven for cross-country skiing and snowshoeing in the winter months.
The town’s primary industries are agriculture and small-scale forestry, reflecting its deep roots in working the land. Windsor’s seclusion is evident in its low population density and the extensive stretches of undeveloped land that surround it.
The quiet roads and panoramic vistas offer residents and visitors a serene experience, far removed from the bustle of city life. Hidden gems like the historic Windsor Jambs, a series of stunning rock formations along the Westfield River, add to the town’s rustic charm.
Where is Windsor?
Located in central Berkshire County, Windsor sits atop the Berkshire Plateau, contributing to its sense of isolation. The town is accessed primarily via Route 9, which connects it to nearby Dalton and Pittsfield but doesn’t bring much through traffic.
Its elevated position and surrounding natural landscapes create a buffer from more developed areas. To reach Windsor, one can enjoy a leisurely drive through the scenic highlands, making the journey a delightful prelude to the tranquility that awaits in this rural community.
3. Peru: Elevated Peace in the Berkshire Hills
Peru, with around 850 residents, is one of the highest towns in Massachusetts, perched atop the Berkshire Hills at an elevation of over 2,000 feet. This elevation provides residents with breathtaking views and a cooler climate, ideal for those who appreciate the tranquility of the mountains.
Recreational activities include hiking the numerous trails, picnicking in Garnet Peak State Reservation, and enjoying winter sports during the snowy months. The town’s economy is modest, focusing on agriculture and small businesses that serve the local community.
Peru’s seclusion is due to its high elevation, vast undeveloped lands, and a network of quiet, winding roads. Its remote location offers a peaceful environment where one can truly disconnect from the hustle and bustle.
Where is Peru?
Nestled in central Berkshire County, Peru is somewhat isolated due to its elevation and the surrounding terrain. The town is accessed via Route 143, a scenic road that climbs through the hills, making the journey both beautiful and serene.
Its location atop the Berkshire Hills means fewer neighbors and less traffic, enhancing its secluded charm. Reaching Peru involves a drive through picturesque landscapes, making the town a perfect destination for those who appreciate the journey as much as the destination.
2. Becket: Serenity Among Lakes and Woodlands
Becket, with a population of approximately 1,800, is a town that offers peace and quiet amidst lakes and forests. Known for its artistic community, it is home to the Jacob’s Pillow Dance Festival, a world-renowned cultural event that adds vibrancy to its serene setting.
Outdoor enthusiasts can enjoy swimming, fishing, and kayaking in the many local lakes, as well as hiking in the nearby state forests. The town’s economy includes arts, tourism, and small businesses that thrive during the summer season.
Becket’s seclusion is evident in its spacious properties, the surrounding woodlands, and the lack of urban development. This creates a haven for those seeking a retreat into nature. Hidden gems like the Becket Land Trust Historic Quarry offer unique explorations of the area’s industrial history amid natural beauty.
Where is Becket?
Situated in the heart of the Berkshires in western Massachusetts, Becket is accessible via the Massachusetts Turnpike (I-90), yet maintains a secluded feel due to its vast natural surroundings. Its location along the Appalachian Trail and proximity to October Mountain State Forest enhances its appeal to nature lovers.
Despite being just off a major highway, the town’s extensive forests and quiet roads keep it tucked away from the hustle of through traffic. Travelers can reach Becket by exiting the Mass Pike at Lee or Westfield and enjoying a scenic drive, making it both accessible and delightfully secluded.
1. Washington: A Hidden Gem Within October Mountain
Washington, with a population of around 550 residents, is a small rural community entirely encompassed by the expansive forests of October Mountain State Forest, the largest state forest in Massachusetts. The town offers unparalleled access to hiking, fishing, and camping, making it a paradise for outdoor enthusiasts.
There are few commercial businesses, emphasizing the town’s quiet, residential nature. Washington’s seclusion is due to its location amid vast woodlands, minimal population, and the absence of major roads cutting through its terrain.
This provides residents and visitors with a peaceful environment and a strong sense of connection to nature. Hidden trails and pristine ponds within the state forest are among the treasures that locals cherish and few outsiders know about.
Where is Washington?
Nestled in central Berkshire County, Washington is surrounded on all sides by October Mountain State Forest. This natural barrier contributes significantly to its secluded character. The town is accessible via Washington Mountain Road, a scenic route that winds through dense forests and over rolling hills.
Its distance from major highways and urban centers ensures a tranquil atmosphere. To reach Washington, visitors can travel from nearby towns like Lee or Pittsfield, embracing the journey through the heart of the Berkshires and into one of the region’s most hidden gems.
