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Town of

Pittsfield

Pittsfield is the phoenix of the Berkshires, having weathered several economic upturns and downturns, while always finding creative ways to reinvent itself. It’s the county seat, and also its commercial and business center. With its eclectic yet easy-to-navigate downtown, diverse population, more affordable real estate, and tight-knit business community, Pittsfield buzzes with commerce, arts, culture, and community. The city hosts a variety of special events, including an Arts Walk, a spring-through-fall Third Thursday street festival, and a summer farmers’ market.

BERKSHIRE-MUSEUM

Small yet impressively varied, the Berkshire Museum hosts exhibits and workshops of art, natural history, and ancient civilization. It also houses a movie theater that showcases the best of independent film.

COLONIAL-THEATRE

Built 1903, this stunning historic theater presents a mix of live and filmed performances, comedy, community events, and other entertainment.

berkshires new york county
Adams Alford Becket Cheshire Clarksburg Dalton Egremont Florida Great Barrington Hancock Hinsdale Housatonic Lanesborough Lee Lenox Monterey Mount Washington New Ashford New Marlborough North Adams Otis Peru Pittsfield Richmond Sandisfield Savoy Sheffield Stockbridge West Stockbridge Tyringham Washington Williamstown Windsor

Adams

Town of

Adams

This North County valley town was founded in 1778 by a group of settlers, including Quakers, whose Meeting House still stands today. It was named after revolutionary leader Samuel Adams (yes, that Sam Adams), and was originally a mill town, producing wool, cotton, lumber, and plastic. These days, Adams is known for its laid-back character and beautiful landscape, which offers multiple options for hiking, snowshoeing, and cross-country skiing.

ASHUWILLTICOOK-RAIL-TRAIL

The site of a Victorian-era rail line, this scenic trail is a must-stop. Ten feet wide, paved, and universally accessible, it traverses 12.2 miles of the stunning Hoosac River Valley.

SUSAN-B.-ANTHONY-BIRTHPLACE-MUSEUM

Suffragist leader Susan B. Anthony was born in this Federalist-style colonial in 1920. It’s now a learning center and museum dedicated to her early years and work as an activist, and is on the National Register of Historic Places.

Alford

Town of

Alford

Quiet, serene, and private, Alford is the town for those who love the feeling of a getaway, every day. A former farming town, Alford strictly controls its residential development to maintain its pastoral charm. It may not have stores, hotels, gas stations, or even a post office, but it does have plenty of wide-open fields, low-traffic roads, and mountain trails, making it the perfect place for biking, jogging, walking, and hiking. With its location between Great Barrington and the border of New York State, you’re always close to shopping and other conveniences.

ALFORD-SPRINGS-RESERVE

Nearly 900 acres of mostly forested ridgeline, plus stunning views of Mount Greylock and Tom Ball Mountain. The reserve has six miles of trails for hiking, snowshoeing, challenging cross-country Nordic skiing, and hunting. And tons of fresh, wild blackberries.

ALFORD-BROOK

This peaceful brook, which runs into the Green River, isn’t just a great spot for a picnic. It’s also considered one of the best spots for fishing in the Berkshires.

Becket

Town of

Becket

Though it’s close to towns like Lee and Lenox, and lies right along the entrance to the Mass Pike, Becket retains its historic wild, wide-open character. With its miles of forests, it’s one of the most colorful Berkshire towns come summer and fall. It’s also full of some of the best real estate values in the county. You’ll find many of its residents out for regular hiking, snowshoeing, and fishing on its make streams, lakes, and ponds. Camping, both individually and as part of sleepaway and day camps, is also popular here.

BECKET-LAND-TRUST-QUARRY

The site of a historic granite quarry in operation for a century, this amazing 300-acre natural landscape was preserved from development thanks to a community fund-raising campaign in the 1990s. Today it’s a favorite place for hiking and critter-watching.

THE-DREAMAWAY-LODGE

This 200-year-old farmhouse on the border of October Mountain State Forest is rumored to have been a brothel and speakeasy during the Great Depression. Its long history of music and performance continues, plus farm-to-table food.

JACOB’S-PILLOW-DANCE-FESTIVAL

The longest-running dance festival in the country, Jacob’s Pillow brings an eclectic mix of internationally lauded dance companies to the Berkshires each year. In addition to year-round performances, the Pillow is an amazing educational resource for dance scholars and professionals.

Cheshire

Town of

Cheshire

This town has always marched to the beat of its own drummer. It has deep entrepreneurial roots, and once boasted saw and grist mills, forges, tanneries, a glass company, and a trip-hammer operation, plus a variety of dairies. Although just 1,500 people lived in Cheshire in 1885, there were four different churches. Today, Cheshire’s rural character prevails, with hundreds of acres dedicated to skiing and hiking, as well as fishing in the Hoosic River.

ASHUWILLTICOOK-RAIL-TRAIL

The trail, which begins in Lanesborough and terminates in Adams, runs most of the length of the town. It’s a popular place for walking, biking, rollerblading, and jogging.

CHEESE-PRESS-MONUMENT

It’s not often you’ll find a monument to an enormous block of cheese. This massive cheese press commemorates a 1,200-pound dairy lover’s delight made by combining the milk of every cow in town and then gifted to Thomas Jefferson, bearing the president’s motto “Rebellion to tyrants is obedience to God.”

Clarksburg

Town of

Clarksburg

On the northernmost border of Berkshire County and Vermont, Clarksburg is known for its small-town feeling and scenic landscape, combining rugged hills with expansive plateaus and tranquil ponds. It’s home to a picturesque state park, and a portion of the Appalachian Trail crosses through town.

CLARKSBURG-STATE-PARK

Camp, hike, ski, or go boating or fishing here. The park contains 368 acres of unspoiled hardwood forest, with memorable views of the Hoosac Range, Mount Greylock, and the Green Mountains.

GOLDEN-EAGLE-RESTAURANT

Located on the Hairpin Turn of the Mohawk Trail, at 1,700 feet above sea level, this building, originally built in 1914, was once a gift shop for trail travelers. It’s now a place to enjoy food, drinks, and spectacular vistas.

Dalton

Town of

Dalton

With its mix of rural and suburban neighborhoods and its compact downtown business district, Dalton has been growing in popularity among Berkshire professionals and families. It was originally a mill and farming community, and its proximity to Pittsfield made it a natural choice for small businesses. Crane & Co., which has made its home here since 1799, is the sole supplier to the US Treasury of cotton-based paper for currency.

STATIONERY-FACTORY

Based in a refurbished mill building, the Stationery Factory houses several businesses and restaurants. It also has a rentable event space, art gallery, and music venue that have hosted everything from workshops to weddings and handmade-goods festivals.

CRANE-MUSEUM

Home to a variety of exhibits on papermaking, viewed through the lens of the country’s oldest paper company, with more than two centuries of the craft under its belt.

Egremont

Town of

Egremont

Egremont hews close to its farming roots, with 20 percent of the land still used for agriculture. It has a charming downtown with shops, cafes, and a post office. On the outskirts of town are dozens of options for outdoor recreation, including biking and walking; and hiking trails, a horseback-riding ring, tennis and volleyball courts, and ball fields at French Park. Egremont has lower property taxes than many of the Berkshires’ best-known towns.

CATAMOUNT-SKI

One of the oldest ski areas in the Northeast, Catamount offers downhill skiing and snowboarding in the winter. Spring and summer are all about the Aerial Adventure Park.

EGREMONT-COUNTRY-CLUB

Tee up at this country club, which has an 18-hole public golf course, driving range, and fully stocked pro shop. Its restaurant is open daily in the warmer months, and has banquet facilities for up to 250 people.

JOHN-ANDREW’S-FARMHOUSE-RESTAURANT

Go to see the old farmstead and ice house, built in the 1700s, and lush perennial gardens. Stay for a cocktail on the terrace, or a meticulously prepared meal made with fresh foods sourced from the local area.

Florida

Town of

Florida

On the far northeast corner of Berkshire County, Florida abuts the Mohawk Trail in the foothills of the Green Mountains. The town’s portion of the Deerfield River is known for having the best trout fishing in the Berkshires. The Hoosac Tunnel, an active railroad tunnel that is widely considered one of the great engineering achievements of the 19th century, is located here. Easygoing and expansive, Florida offers a quiet, outdoorsy lifestyle that’s within easy driving distance of both the Central Berkshires and the Pioneer Valley.

MONROE-STATE-FOREST

For hiking, horseback riding, cross-country skiing, and some beautiful vistas of the Deerfield River, pay a visit to Monroe State Forest. You’ll also find remnants of the land’s farming past, including stone walls and cellar holes.

WHITCOMB-SUMMIT-RETREAT

On 19 mountaintop acres, this hotel and banquet center boasts out-of-this-world views. It offers lodging, dining, and party facilities for weddings.

Great Barrington

Town of

Great Barrington

Hailed as one of the top small towns in America by magazines such as Smithsonian and Vogue, Great Barrington is a melting pot of big-city ideas and small-town friendliness. Its downtown is bustling with shops, galleries, cafes, and restaurants. Night life is lively, with music, dozens of dining options, a movie and a live-performance theater, and a variety of special events. Venture outside to one of the region’s best farmers’ markets, plus an eclectic group of stores. Or get your outdoor fix with skiing and snowboarding at Ski Butternut, hiking on Monument Mountain, or kayaking and canoeing on Lake Buel.

SKI-BUTTERNUT

A longtime favorite of Massachusetts skiiers, Butternut has 22 trails, 10 ski lifts, 2 terrain parks, a snow tubing hill, and a ski school.

W.E.B.-Dubois-National-Historic-Site

This National Historic Landmark celebrates the early life of civil rights activist, author, and visionary W.E.B. Du Bois, who lived here for several years.

art-center

This 1920s Art Deco theater hosts wide-ranging performances, from dance and musicals to stand-up comedy and opera.

Hancock

Town of

Hancock

With its unusual “bowling alley” shape, Hancock stretches lengthwise across the border of the Berkshires and New York State, and touches seven different towns. It was named for a politician with a pretty famous signature, and has the lowest property-tax rate in all of Berkshire County. It’s both pastorally rich and forward-thinking, boasting both an awe-inspiring landscape, especially in the fall, and the county’s first wind farm.

JIMINY-PEAK-MOUNTAIN-RESORT

The largest ski and snowboard resort in southern New England, Jiminy generates its own energy, including for snow-making, through wind power. A four-season resort, it also has a summer Mountain Adventure Park, and restaurant, conference, and wedding facilities.

IOKA-VALLEY-FARM

Stop at Ioka Valley for a maple sugaring tour, then stick around for pancakes topped with syrup made right here at the farm. Ioka Valley also sells specialty maple products, plus beef, pumpkins, squash, and Christmas trees, all grown or raised on premises.

HANCOCK-SHAKER-VILLAGE

This 750-acre living-history museum straddles both Pittsfield and Hancock. View the 20 original Shaker buildings and extensive collections of Shaker furniture and artifacts, or take a workshop, go for a hike, have a picnic, or visit the farm animals.

Hinsdale

Town of

Hinsdale

Settled in 1763 and originally called Partridgefield, after a wealthy benefactor, Hinsdale was renamed in 1804 after a family who owned the wool mill that supported the town’s economy for two decades. Calm, scenic, and open, Hinsdale is a good choice for those who like to have room to move—or to keep livestock and pets. Hinsdale also has five areas for camping.

BAS-RIDGE-GOLF-COURSE

A public, 18-hole golf course with a rating of 63.7, Bas Ridge also has a bar and snack bar.

LAKE-ASHMERE

Three of the town’s summer camps—Camp Ashmere, Camp Danbee, and Camp Taconic—are located along the lake. It’s also used for fishing, boating, rowing, and swimming.

Housatonic

Town of

Housatonic

Although it’s classified as a small village at the northeastern edge of Great Barrington, Housatonic has a personality all its own. One of the region’s busiest mill towns in the 19th century, it has been reinvented as an outdoor and artist’s haven. Its buildings and landscape along the Housatonic River are a favorite subject for amateur and professional photographers, and there are several galleries and entertainment venues in its downtown. Housatonic is also a great place for biking, walking, and cross-country skiing, as well as youth basketball games at the Housy Dome.

BERKSHIRE-MOUNTAIN-BAKERY

Featured in the Netflix documentary Cooked, this is the original sourdough bakery in the Berkshires. Pick up a wide range of breads, pastries, desserts, and more.

BERKSHIRE-PULSE

With its mix of dance, world music, and movement arts, Berkshire Pulse is a dynamic place to for kids, teens, and adults to learn about and enjoy the benefits of movement and music.

GUTHRIE-CENTER

Founded by songwriter Arlo Guthrie, this restored church is dedicated to cultural preservation, education, and community outreach. It hosts a popular Troubadour Series of live music each year.

Lanesborough

Town of

Lanesborough

A center for agriculture and marble export during the 1800s, Lanesborough possesses some truly beautiful neighborhoods sited on old farmland. It also has a variety of restaurants, shopping areas, and places for family fun, including Mount Greylock, the Berkshires’ premier place for hiking. Lanesborough’s central location makes it easy to travel into Pittsfield and Lenox to the South or North Adams and Williamstown to the north, for even more entertainment and commercial services.

MOUNT-GREYLOCK

There are no bad views from Mount Greylock, which rises 3,491 feet—the highest point in Massachusetts—and boasts dozens of moderate to advanced hiking and cross-country ski trails. Hike to the peak and visit the War Memorial Tower, or enjoy dinner and music at Bascom Lodge.

RAMBLEWILD

Whether you’re a beginner or an expert, you’ll have a blast in Ramblewild’s aerial adventure park, featuring obstacle courses and ziplining, plus hiking. It’s run by Feronia Forests, whose mission is to preserve ecosystems and educate the community about sustainability.

PONTOOSUC-LAKE

A popular gathering spot since the 1800s, Pontoosuc has a variety of vacation rentals and spots for camping along the water. Or go fishing, canoeing, kayaking, boating, or waterskiing.

Lee

Town of

Lee

After its mills folded in the early 20th century, Lee seemed destined to be a blip on the radar of New England history. But an extensive downtown revitalization project brought the town back to vibrant life, and its antique Main Street buildings onto the National Register of Historic Places. Known as the Gateway to the Berkshires, for its location right on the Mass Pike, the town has a variety of shopping, restaurants and bars, community services, and special events.

DOWNTOWN-LEE

The heart of Lee’s business district, Main Street is on the National Register of Historic Places. You’ll find a range of cafes, restaurants, shops, and galleries here and on adjacent streets.

OCTOBER-MOUNTAIN-STATE-FOREST

It’s hard to find a prettier place to hike than October Mountain, which is made up of 16,400 acres of forest and recreational preserve.

PREMIUM-OUTLETS

Some of the best values in the Berkshires can be found at the Premium Outlets. Choose from more than 60 clothing, accessories, shoe stores, and more.

Lenox

Town of

Lenox

Once the playground of the well-heeled from the Victorian and Industrial eras, Lenox has had a long love affair with artists and celebrities—from authors Nathaniel Hawthorn and Catharine Sedgwick to actress Fanny Kemble and musician James Taylor. It’s been the cultural heart of the Berkshires for centuries, which makes it one of the county’s most-visited towns. Postcard-pretty and cosmopolitan-minded, Lenox is chock-full of sites for hiking, biking, shopping, antiquing, art, golfing, lodging, and dining.

THE-MOUNT

The summer “cottage” of novelist Edith Wharton, The Mount is now both a museum and a learning center, featuring talks by a host of well-regarded authors. Don’t miss the impeccably restored gardens.

PLEASANT-VALLEY-WILDLIFE-SANCTUARY

Owned by the Massachusetts Audubon Society, this nature preserve features hiking trails, exhibits, and great spots for watching beavers, owls, and other wild creatures.

SHAKESPEARE-&-COMPANY

Professional live theater, including both Shakespeare’s works and other classic and contemporary plays. It’s is also home to an impressive actor training and theater-in-education program.

Monterey

Town of

Monterey

Originally a part of neighboring Tyringham, Monterey is a relaxed, unspoiled town along the Mill River in the southern Berkshires. Brimming with wildlife and opportunities for outdoor recreation, Monterey is a fantastic choice for lovers of swimming, fishing, boating, hiking, cross-country skiing, and skating. Make a special stop at the Monterey General Store for snacks, housewares, and gifts. And don’t miss the dramatic vista of Lake Garfield and the forests surrounding it from the overlook at Beartown State Forest.

BEARTOWN-STATE-FOREST

It’s not just for hiking: Beartown, located on 12,000 acres of state forest, is a favorite among locals for swimming, boating, and fishing in the summer, and cross-country skiing and snowmobiling in the winter.

BIDWELL-HOUSE-MUSEUM

Built in 1760 as a parsonage, the Bidwell House is now a museum that documents early settlement of the Berkshires. The building and 192 acres of grounds and hiking trails have been authentically restored.

LAKE-GARFIELD-&-TOWN-BEACH

Hike through the forests, go fishing or boating, or relax along the shore of the 262-acre Lake Garfield.

Mount Washington

Town of

Mount Washington

Located on a plateau in the Taconic Mountains, Mount Washington is the smallest town, by population, in the Berkshires. Petite in size but mighty in spirit, Mount Washington is ideal for those who love quiet and privacy, and being surrounded by the sights and sounds of nature. Its borders touch towns in Massachusetts, New York, and Connecticut.

GARRETT-GARDEN

This public park features a perennial garden, green, labyrinth, and arboretum. The green transforms into a playing field in the summer, hosting 10 Sunday-afternoon baseball games.

New Ashford

Town of

New Ashford

New Ashford, tucked between Lanesborough and Williamstown, is one of Berkshire County’s smallest towns in land area, clocking in at 13.5 square miles. It was founded in 1762 and named for the town in Connecticut where its founders were from. Much like Dixville Notch, New Hampshire, New Ashford was once the first town to cast votes in presidential elections. Today it retains much of its original pastoral character and sweeping wooded landscape.

SADDLE-BALL-MOUNTAIN

The second-highest peak (after Mount Greylock) in Massachusetts, Saddle Ball is part of a series of outcroppings that wind along the southern ridge of the Mount Greylock range. A hike on Saddle Ball will take you through a variety of microclimates, with a variety of trees and dazzling wildflowers.

MILL-ON-THE-FLOSS

Watch your meal of classic French country cuisine being prepared in the open kitchen of this restaurant, located in an 18th-century farmhouse. Mill on the Floss has been owned and operated by the same family for nearly a half century.

New Marlborough

Town of

New Marlborough

One of the first Berkshire towns to be settled in the 18th century, New Marlborough is historic but not old-fashioned, sophisticated but never pretentious. Though just under 50 square miles, New Marlborough contains five villages: Clayton, Hartsville, Mill River, New Marlborough Village, and Southfield. Its scenic green is rimmed by a historic village center that buzzes with activity, especially in the warmer months. From its lakes to its forests and waterfalls, New Marlborough is relaxed New England living at its most beautiful.

DRY-HILL

Open year-round, this nature preserve is made up of woods, ridgelines, summits, valleys, vernal pools, and other wetlands. It plays host to spectacular blooms of mountain laurel and other flowers, as well as dozens of woodland birds. Keep your eyes peeled for the black-throated blue warbler.

CAMPBELL-FALLS

Located within Campbell Falls State Park, this dramatic waterfall drops 50 feet into a rocky gorge.

LAKE-BUEL

One of the most beloved lakes in the Berkshires, Buel is the year-round home of about a dozen families. In the summer, those numbers blossom to 225 families, plus campers. Swimming and boating are popular here.

North Adams

Town of

North Adams

A manufacturing powerhouse during the Industrial Revolution, with dozens of mills, machine shops, marble works, and carpentry businesses, North Adams has been reborn into a center of arts, culture, small business, and outdoor recreation. The Appalachian Trail runs through part the city, and has several scenic overlooks and wooded and pastoral areas. Many of the historic brick mill buildings have been repurposed into offices, co-working spaces, and art galleries. Bold, innovative, and forward-thinking, North Adams has become the go-to city for entrepreneurs, artists, and a variety of community organizations.

MASSACHUSETTS-MUSEUM-OF-CONTEMPORARY-ART-(MASS-MOCA)

One of the largest and most celebrated museums and performing arts spaces in New England, MASS MoCA has distinguished itself with its diversity of thought-provoking modern collections and live music, dance, and performing art.

HOUGHTON-MANSION

The former home of printing impresario Albert Charles Houghton, this lavish building has had a uniquely spooky history. It was featured on the Travel Channel show Ghost Adventures, but is not currently open to tours of the interior.

NATURAL-BRIDGE-STATE-PARK

An incredible day trip, this 48-acre park, a former marble quarry, features the continent’s only naturally formed white marble arch (which dates to the Paleolithic Era) and man-made white marble dam.

Otis

Town of

Otis

Located in southern Berkshire County and close to the Mass Pike and points east, Otis is small and quaint, yet diverse in landscape. It features a large reservoir and several streams and ponds, plenty of wide-open fields and green spaces, and hills with elevations rising to nearly 2,000 feet. Otis is known for its laid-back attitude, and its residents’ love of the outdoors.

OTIS-RIDGE

Since 1947, this ski area has almost 100 percent snowmaking capacity. It offers both day and night skiing.

OTIS-RESERVOIR

Created by dam at the confluence of three ponds, the reservoir was originally used for powering the mills along the Farmington River. Seasonal and year-round homes have been built all around the reservoir, which is open to fishing, boating, and canoeing.

Peru

Town of

Peru

Settled in 1767, the town, so the story confusingly goes, was named “because it is like the Peru of South America, a mountain town, and if no gold or silver mines are under her rocks, she favors hard money and begins with a P.” Peru rocks the highest town elevation in Massachusetts, at over 2,000 feet. Two large and beautiful wildlife management areas reside in the northern and southern thirds of town, and the east has a number of scenic brooks. Located on the eastern edge of the Berkshires, Peru provides unspoiled natural beauty and a relaxed home haven, especially for those commuting to Pittsfield, Northampton, and Springfield for work.

DOROTHY-RICE-WILDLIFE-SANCTUARY

Tranquil and spectacularly beautiful, this nature preserve has 286 acres of hiking and walking trails through and around woodlands, meadows, and a pond.

PERU-STATE-FOREST

This enormous park, covering 2,750 acres of trails and scenic vistas, is ideal for hiking, birdwatching, snowmobiling, hunting, and fishing. At Garnet Peak, visit the memorial to World War II paratroopers whose transport plane crashed on the mountain in heavy fog.

Pittsfield

Town of

Pittsfield

Pittsfield is the phoenix of the Berkshires, having weathered several economic upturns and downturns, while always finding creative ways to reinvent itself. It’s the county seat, and also its commercial and business center. With its eclectic yet easy-to-navigate downtown, diverse population, more affordable real estate, and tight-knit business community, Pittsfield buzzes with commerce, arts, culture, and community. The city hosts a variety of special events, including an Arts Walk, a spring-through-fall Third Thursday street festival, and a summer farmers’ market.

BERKSHIRE-MUSEUM

Small yet impressively varied, the Berkshire Museum hosts exhibits and workshops of art, natural history, and ancient civilization. It also houses a movie theater that showcases the best of independent film.

COLONIAL-THEATRE

Built 1903, this stunning historic theater presents a mix of live and filmed performances, comedy, community events, and other entertainment.

Richmond

Town of

Richmond

Richmond has long been one of the Berkshires’ most desirable towns, thanks to its spectacular rolling landscape, secluded neighborhoods, and impressive estates, many of which have remained in the same families for generations. Its Central County location means you’re never far from modern conveniences and entertainment, yet it’s full of places for biking, hiking, snowshoeing, or cross-country skiing, or canoeing and kayaking on Richmond Pond. The town also boasts some of the best apple picking in the region.

BARTLETT’S-ORCHARD

Now run by the fourth generation of Bartletts, this orchard produces 20,000 apples on 52 acres of orchard each year. Pick your own, or head to the farm store for bagged apples, cider doughnuts and other pastries, and apple cider.

HILLTOP-ORCHARDS-&-FURNACE-BROOK-WINERY

Known for its Johnny Mash hard cider, Hilltop Orchards also makes and sells its own wines, cider doughnuts, and apple pies. It’s one of the top choices in the Berkshires for apple picking. Don’t miss the guided full-moon hikes or snowshoeing on the orchard’s extensive system of trails.

RICHMOND-POND

Canoeing, kayaking, fishing, and swimming are all popular at this 218-acre pond. Its town beach is a great place to kick back and relax with a book, or set up a play date for the kids.

Sandisfield

Town of

Sandisfield

Large in land area yet small in population, Sandisfield is a scenic town along the Farmington River Valley. It has historically been a logging town, even to this day, but also features several farms, orchards, and nurseries, as well as small businesses. Outdoor recreation is serious business in Sandisfield, with a state forest, two rivers, and two parks.

SANDISFIELD-ARTS-CENTER

Built in 1839 as a Baptist meeting house, this building now offers a range of live performances, exhibits, and workshops.

NEW-BOSTON-INN

Once a popular stagecoach stop, the inn is the oldest in Berkshire County. It also has a restaurant and tavern, a parlor for friendly gathering, and outdoor gardens.

Savoy

Town of

Savoy

On the northeastern border of Berkshire County, Savoy’s roots are in agriculture and lumber. It’s a small and quiet community, with a pretty landscape of sweeping panoramic views and tree-lined neighborhoods. The northern part of town is home to several brooks and a portion of the Deerfield River. Savoy is convenient to both North and Central Berkshire County, as well as to towns in the Pioneer Valley.

SAVOY-MOUNTAIN-STATE-FOREST

With its secluded location, Savoy Mountain doesn’t get as much traffic as some of its neighbors; this makes for a peaceful and unhurried hiking experience. The highest point is Borden Mountain, at about 2,500 feet. There are also four ponds and two waterfalls, including Tannery Falls, which plunges dramatically into a pool from nearly 100 […]

Sheffield

Town of

Sheffield

Made up of two villages and a varying landscape that includes floodplains, wetlands, fields, and mountain slopes, Sheffield is practically the postcard for bucolic New England towns. It’s the oldest town in the county, founded in 1724, and sticks close to its agricultural roots. Only 2.5 hours from New York City, it’s a favorite of second-home owners and professionals who frequently commute in to the city. Sheffield has a small business district, as well as a growing arts scene. It’s also widely known as one of the hottest antiquing spots in the area.

ASHLEY-HOUSE

The former home of Colonel John Ashley, one of the town founders and a supporter of the American Revolution. It was also the home of the slave Elizabeth Freeman, or Mum Bett, who sued Ashley for her freedom and won—and helped end slavery in Massachusetts.

BARTHOLOMEW’S-COBBLE

Off the beaten path, ruggedly beautiful, and filled with mountain vistas and 800 species of plants, this preserve has a unique landscape. Based on a 100-foot-high bedrock outcropping, it features hiking paths that wind through two rocky knolls, forests, and flat land.

SHEFFIELD-POTTERY

One of the country’s premier clay makers and ceramics supply stores, Sheffield Pottery is a mecca for ceramics artists of all levels.

Stockbridge

Town of

Stockbridge

The names Norman Rockwell and Stockbridge go hand-in-hand, thanks to the artist’s many works based on his town—the community still reenacts his Stockbridge Main Street at Christmas painting each year during its holiday festival. But it was also the home of luminaries like sculptor Daniel Chester French and the Sedgwick family. With its antique look and busy shops, galleries, and cafes, the downtown makes a worthy day trip at any time of year. Or go hiking, kayaking, boating, swimming, or paddleboarding on Stockbridge Bowl, one of the most scenic spots in the Berkshires.

CHESTERWOOD

The summer estate and studio of Daniel Chester French, who created the Lincoln Memorial in Washington, DC. The 150-acre property houses a museum and an impressive outdoor sculpture garden with rotating contemporary exhibits.

KRIPALU-CENTER-FOR-YOGA-&-HEALTH

For decades, Kripalu has been known for its health and wellness programs, including yoga, meditation, and nutrition. It offers a comprehensive slate of programming throughout the year, with workshops on fitness, creativity, writing, and personal and spiritual connection.

NAUMKEAG

Built as the home of 19th-century diplomat Joseph Hodges Choate, Naumkeag was designed by internationally renowned architect Stanford White. Tour the home and grounds, or attend a special event, like cocktails in the garden, a Halloween haunted house, or Winterlights, when the grounds are decked out with thousands of holiday lights.

West Stockbridge

Town of

West Stockbridge

West Stockbridge might seem like the little sister to Stockbridge, but its profile has been rising over the past decade, thanks to an influx of new residents and businesses. Its sweet, walkable downtown is the major draw, but it also boasts two of the county’s best restaurants, as well as a growing arts scene. Like many towns in the Berkshires, West Stockbridge also has dozens of outdoor activities, from canoeing, kayaking, boating, and fishing, to biking, walking, and hiking. Or visit the pick-your-own farms for apples, blueberries, and pumpkins, or go foraging for wild foods.

SHAKER-MILL-BOOKS

This extensive shop specializes in new books about the Berkshires, as well as used, rare, and out-of-print books.

YOKUN-RIDGE

Part of the Taconic Mountains, this hiking area has a series of contiguous peaks with scenic views.

TURN-PARK-ART-SPACE

A former marble quarry, Turn Park has been transformed into an open-air museum, sculpture park, and performance space. It also hosts community markets and events.

Tyringham

Town of

Tyringham

Settled in 1735, Tyringham was once home to a Shaker community with the holy moniker of Jerusalem. It’s now an easygoing rural community, with wide-open fields and meadows abutting green forests and swooping hills. Close to Lee and the Mass Pike, Tyringham is a terrific home base for those who love peace and quiet but still want to be close to modern conveniences.

TYRINGHAM-COBBLE

Formed from millennia-old tectonic shifts that created a high ridge topped by exposed bedrock, this nature preserve features orchards, forests, fields of wildflowers, and panoramic valley vistas at the summit.

ASHINTULLY-GARDENS

Composer John McLennan created these interconnected gardens over a 30-year period. With their elegant design and intimate feel, they’re an inspiring place to walk, relax, and reflect.

Washington

Town of

Washington

This small town went through three name changes before being named after George Washington. A mountainous town bounded by October Mountain and the Appalachian Trail to the west, it was a stop on the stage road from the east into Pittsfield. Rural then and today, what Washington doesn’t have in industry it makes up for in natural beauty. Many residents enjoy a variety of winter spots, including cross-country skiing, snowmobiling, and snowshoeing.

Williamstown

Town of

Williamstown

Williamstown has been included in no less than a dozen best-of travel articles, in The New York Times, Architectural Digest, Conde Nast Traveler, Curbed Boston, and more. This is partly thanks to its quintessential New England look, walkable downtown, and dozens of choices for arts, culture, and dining. It’s the home of the highly regarded Williams College, as well as a world-class art museum and summer theater festival. Williamstown’s location and eclectic character makes it a favorite among professionals, academics, families, and artists alike.

STERLING-AND-FRANCINE-CLARK-ART-INSTITUTE

A combination art museum and center for research and higher education, the Clark stands out among American art institutions. It features frequently changing exhibitions from both its permanent, classical collection, and modern art, plus lectures and performances.

WILLIAMS-COLLEGE-MUSEUM-OF-ART

A fascinating and expertly edited collection of visual art, owned and managed by Williams College. The museum also offers public programs.

’62-CENTER-FOR-THEATRE-AND-DANCE

As architecturally beautiful as it is innovative in its programming, the ’62 Center was created as a performance venue for Williams College student actors, dancers, designers, and musicians. It hosts a variety of open-to-the-public student and professional performances year-round.

Windsor

Town of

Windsor

Founded in 1771, Windsor was originally a mill, farming, and logging community. With its many wildlife areas, breathtaking vistas, ponds, and unspoiled woodlands, Windsor has dozens of opportunities for hiking, hunting, kayaking, snowshoeing, and cross-country skiing. It’s home to the Eugene Moran Wildlife Management Area, and parts of the Savoy and Peru Wildlife Management Areas also cross into the town.

NOTCHVIEW

Set on 3,100 acres, Notchview is a top pick in the winter for snowshoeing and Nordic skiing, on 17 kilometers of groomed cross-country and 8 kilometers of skate-skiing trails. It also offers trails for “skijoring,” or skiing with dogs (no kidding!). Notchview is open year-round for hiking and birdwatching.

WINDSOR-STATE-FOREST

Looking for a place to hike, explore waterfalls, horseback ride, mountain bike, cross-country ski, or swim? Windsor State Forest has it all. Don’t miss the Windsor Jambs waterfall, which splashes into a gorge from nearly 80-foot-high granite walls.

Buying a home or property is one of the most exciting and important purchases you’ll make. It’s an investment in a community, and in your and your family’s happiness. But the process is more than just dotting a few i’s and crossing some t’s.

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