Mass Moca
1040 Mass MoCA Way
North Adams, MA
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The Massachusetts Museum of Contemporary Art (MASS MoCA) is a museum in a converted Arnold Print Works factory building complex located in North Adams, Massachusetts. It is one of the largest centers for contemporary visual art and performing arts in the United States.
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5 Prospect Hill Rd
Stockbridge, MA
This Gilded-Age “cottage,” designed in 1884 by McKim, Mead, & White as the summer estate for the family of Joseph and Caroline Choate, boasts original furnishings and art in its 44 rooms as well as magnificent gardens.
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Stockbridge, MA
Summer home of the Boston Symphony Orchestra also offering a wide variety of musical performances, Van Morrison, Bonnie Raitt, Ringo Starr, Judy Collins and many more.
Clark Art Institute
225 South St
Williamstown, MA
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Clark Museum, located at the Clark Freeport Zone in Pampanga, showcases various important artifacts, military memorabilia, and local products that depict the history of Clark from 1901 until its present progression into an economic and Freeport Zone
Norman Rockwell Museum
9 Glendale Rd
Stockbridge, MA
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The Norman Rockwell Museum in Stockbridge, Massachusetts, must be one of the most popular museums in the world,” wrote author Paul Johnson, “crammed from dawn till dusk with delighted visitors crowding round the originals of much-loved paintings.
Eric Carle Museum of Picture Book
125 W Bay Rd, Amherst, MA 01002
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They collect, preserve, and exhibit original illustrations, encourage guests of all ages to read and create art, and foster an ever-growing audience passionate about children's literature.
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2 Prospect Hill Rd, Stockbridge, MA 01262
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This 350-acre property of the Catholic Church, a ministry of the Marian Fathers of the Immaculate Conception, features statues, candle shrines and memorials, plus the soaring shrine itself, illuminated by 36 stained glass windows and graced with intricate woodwork, mosaics, and carved marble.
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2 Plunkett St
Lenox, MA
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Visit the estate of Edith Wharton – including her personal library, the boudoir where she wrote her classic novels, as well as three acres of formal gardens – who designed her own 1902 “cottage” in accordance with the principles set forth in her influential book, The Decoration of Houses. The Mount presents exhibits, workshops, talks, readings, music, and theatrical performances. Fans of the author won’t want to miss The Wharton Salon’s dramatic adaptations of her work, staged each summer.
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5 W Stockbridge Rd
Stockbridge, MA
The Berkshire Botanical Garden, is one of New England’s oldest and most treasured public gardens encompassing 15 acres of cultivated land in Stockbridge, Massachusetts. Its collections contain over 3,000 species and varieties, with an emphasis on plants that thrive in the Berkshires. Classes, workshops, lectures and special events are offered year-round.
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92 Hawthorne St, Lenox, MA 01240
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A must-see for fans of mid-century modern design. The studio of abstract artist George L.K. Morris, built in 1930, is the earliest example of Modern architecture in New England. In 1941 Morris expanded the structure to integrate a home for him and his wife, fellow artist Suzy Frelinghuysen. Their artwork shares wall space with their more famous contemporaries, including Picasso, Braque, and Leger.
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1843 W Housatonic St
Pittsfield, MA
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Home to the Shakers for more than 220 years, Hancock Shaker Village is now an outdoor history museum dedicated to preserving the Shaker legacy and making that story relevant and illuminating for today’s visitors. Situated on 750 acres of picturesque farm, field, and woodland in the bucolic Berkshires of Massachusetts, the Village consists of 20 historic buildings, a working farm and heirloom gardens, and a premier collection of 22,000 authentic Shaker artifacts.
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19 Main St, Stockbridge, MA 01263
The oldest house in Stockbridge, built in 1739 by the Reverend John Sergeant – missionary to the Stockbridge Indians – provides a glimpse of Colonial life and Native American history.
Chesterwood
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4 Williamsville Rd, Stockbridge, MA 01262
A Property of the National Trust for Historic Preservation, Chesterwood was the summer estate of sculptor Daniel Chester French, who created the seated figure of Abraham Lincoln in the Lincoln Memorial and The Minute Man statue in Concord, Massachusetts. Tour his Gilded-Age home, studio and gardens, or stay overnight in his secret studio, Meadowlark, which is operated as a guesthouse by the Red Lion Inn.
Kennedy Park
275 Main St
Lenox, MA
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If you’re looking for more outdoor activities in Lenox you can visit Kennedy Park. This lovely park has nearly 15 miles of trails that are well-suited for biking and hiking. You can even pack a nice picnic and enjoy the beautiful views with family and friends. There are trails that you can take kids on as well, so if you’re taking a family trip out there, you don’t have to worry about the trails being too tough for your kids to walk.
Laura Lookout Tower
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Stockbridge, MA
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Laura’s Tower & Ice Glen: Laura’s Tower trail will take you through old pine and hemlock forest, rock outcroppings, birch and mountain laurel. The reward at the end of this steep 3/4 mile assent is the relic of an old metal fire tower, which offers a panoramic view of the Berkshires, NY Catskills and Vermont’s Green Mountains. On the Ice Glen trail you will climb over and around magnificent rock outcroppings as you navigate though this magical glacial ravine, lined with old growth trees, the oldest in the northeast. The Glen stays cool year round, and you may even see snow and ice in the middle of summer! A host favorite, and a must see in Stockbridge.
Mount Greylock State Reservation Visitor Center
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30 Rockwell Rd
Lanesborough, MA
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At 3,491 feet, Mount Greylock is the highest point in Massachusetts. From its peak on a clear day, you can see as far as 90 miles away. No matter when you visit, there's plenty to do & see. Drive up, hike around, picnic with panoramic mountain views around you.
Laurel Lake
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MA
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Laurel Lake offers swimming, hiking, horseback riding, fishing and boating. (It has a boat launch, is stocked with trout & broodstock salmon.) The grounds include 8 miles of forest roads, Edith Wharton’s estate, The Mount, and beautiful gardens In the winter, there is ice fishing and skating.
Stockbridge Bowl
Stockbridge, MA
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A wide variety of outdoor recreation is readily available here in the Berkshires. Hiking, biking, skiing, lakes, mountains, and more. Of course, once the mercury starts creeping up the thermometer, people make a beeline for the water. While the Berkshires are home to quite a few bodies of water, one of the largest and most popular is the Stockbridge Bowl.
Olivia's Overlook
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Hiking Trails
West Stockbridge, MA
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Breathtaking views of Stockbridge and a great country drive! To have a wonderful country drive, set your GPS for West Stockbridge then again set it for Olivia’s overlook and you’ll love the drive there. Then continue down to Stockbridge.
Lake Mansfield
Great Barrington, MA 01230
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The pond is open to the public for seasonal recreation. Visitors are welcome. A parking area provides access to the sandy beach front, grassy shaded picnic area, swings, and forest trails. Portable toilets are available May through September. Visitors to the Lake Mansfield Recreation Area enjoy swimming, boating, picnicking, fishing, walking trails and nature watching. The beach area is closed to pets. Dogs are welcome to access the lake at the boat launch area. The Lake Mansfield Recreation Area allows for road and forest trail walks, giving visitors opportunities to enjoy the beauty and wildlife of the lake and forest. The Lake Mansfield Conservation Forest features an accessible trail network within a 29-acre woodland. The majority of the trail is built to accessible standards, including gentle slopes and a crushed stone trail surface. The shady trails provide a complement to the open lake.
Bash Bish Falls State Park
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Falls Road
Mount Washington, MA
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Short easy hike from the lower parking lot next to or close to the river. Bash Bish Falls State Park, but I suggest to use the parking in Taconic State Park, and the trail up from there, as you can find a small swimming pond and an iron works trails too from the same spot.
Jug End State Reservation And Wildlife
Egremont, MA 01230
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1,158-acre Jug End offers some of the best scenic views of the Berkshires. In addition to having its own trails, Jug End also offers access to and parking for the Appalachian Trail. You can hike, hunt and fish here.
Bartholomew's Cobble Reservation
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105 Weatogue Rd
Sheffield, MA
Ashley Falls
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Bartholomew’s Cobble is located in Sheffield, Massachusetts. This private reserve has approximately 5 miles of moderate hiking trails. The cobble is mostly limestone and marble, which alters the soil and creates a unique environment that supports a wide variety of flora. You can either hike up Hurlbut’s trail for scenic overview of the area, or hike the low-lying trails along the Housatonic. There is an admission fee. Dogs are not allowed.
Hollow Fields
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Perry Peak Road
Richmond, MA
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The 660+ acres of linked hayfields and forests of the Hollow Fields reserve offer the Berkshires’ best view of Yokun Ridge, and abundant bobolinks nesting in the grasslands. Enjoy walking the path through the fields or explore the trails and woods roads in adjoining forestland, including a 45-acre parcel owned by the Town of Richmond.
Mass Audubon Canoe Meadows Wildlife Sanctuary
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309 Holmes Rd
Pittsfield, MA
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Nice looped trails, mostly flat and wooded, some through wetland areas. Beautiful large pines and a nice meadow view at the start of the hike. It's very close and makes a good quick walk.
Benedict Pond Loop
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Great Barrington, MA
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Benedict Pond is a great place to swim. It's a beautiful drive getting there. The pond is located inside Beartown State Park but drive through Stockbridge for a better ride as the Lee entrance is a rough road.
Roaring Brook Trail
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Williamstown, MA
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Head out on this 6.6-mile out-and-back trail near Keene Valley, New York. Generally considered a challenging route. This is a very popular area for hiking and snowshoeing, so you'll likely encounter other people while exploring. The best times to visit this trail are February through October. Dogs are welcome, but must be on a leash.
October Mountain State Forest Campground
256 Woodland Rd
Lee, MA
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At 16,500 acres, October Mountain is the largest state forest in Massachusetts. You'll find trails for any level of hiking experience, and you can also visit nearby Tanglewood, popular music venue and home to the Boston Symphony Orchestra.
Umpachene Falls
New Marlborough, MA 01259
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At Umpachene Falls Park, the Umpachene River dumps into the Konkapot River in a small park maintained by the town of New Marlborough. You will need inside connections to visit this waterfall: the park is for New Marlborough residents and their guests only. However, if the grounds-keeper is on-site, they may grant you access if you ask politely and promise to respect the park by leaving no trace of your visit.
Swimming is not only allowed here, it is encouraged! Children will love to swim in the lazy Konkapot River, while adults will enjoy wading in the pools of Umpachene Falls. There are tables and swings in the park, so bring a lunch and budget at least a few hours to enjoy this charming little park.
Onota Lake Beach
Pittsfield, MA
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Onota Lake is a 617-acre lake located entirely within the City of Pittsfield and is owned and managed by the City of Pittsfield. Many recreational opportunities are provided by the lake and are enjoyed by area residents as well as those visiting the Berkshires. However, like many area lakes, Onota Lake is threatened. While these problems are not unusual, atypical, or severe, they do require attention.
Gould Meadows
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110B Interlaken Rd
Stockbridge, MA
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Gould Meadows is a nature reserve in Massachusetts. Gould Meadows is situated nearby to the hamlets Camp Mah-Kee-Nac and Tanglewood.
Lake Garfield Beach
78 Tyringham Rd
Monterey, MA
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Nice sand, picnic tables, grassy area, port-a-john, and a big roped off swimming area with docks to sunbathe on - all the makings of a perfect afternoon!
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Becket Quarry
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456 Quarry Rd
Becket, MA
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The quarry, known during its operating days as the Chester-Hudson Quarry, played a key role in the early development of the Town of Becket and the surrounding area. Granite from this quarry was used for monuments in many states. The quarry was operational from the 1860’s to the 1940’s.
When the quarry was abandoned, much of the equipment and structures were left just as it was (as if the quarrymen had gone for lunch and never returned). The site has stayed the same, plus some rust, until now.
The Historic Quarry and Forest is open year round, dawn to dusk, and admission is free to the public.
Balderdash Cellars
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81 State Rd
Richmond, MA
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This local winery has a fantastic outdoor seating area/amphitheater with expansive views. They have a regular schedule of musical guests, and a food truck on weekends.
Canterbury Farm
1986 Fred Snow Rd
Becket, MA
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Canterbury Farm, located in the beautiful Berkshire Hills of Massachusetts, offers fun for the whole family with skiing, skating, snowshoeing, skating, snowshoeing, rentals. We offer bed-and-breakfast lodging in our guest rooms only during the summer months. Display gardens and Music in the Garden events are also located on this historic site.
Becket Land Trust & Historic
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12 Brooker Hill Rd
Becket, MA
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The historic quarry and nature conservancy has walking trails, railroad and mining artifacts and swimming (for the daring) in the quarry itself. And for the really daring, cliff jumping, EPIC cliff jumping! Local teen hangout and did I mention the cliff jumping?
Tolland State Forest
Tolland, MA 01034
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At the center of Tolland State Forest sits the 1,065-acre Otis Reservoir, which offers a variety of recreational activities. A boat launch is available for boats up to 24 feet in length. No watercraft, except pontoon or sail powered boats, may exceed 24 feet in length. No boats with bathrooms are allowed on the Otis Reservoir.
Otis Reservoir
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Otis, MA 01029
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Otis Reservoir is the largest natural body of water in Massachusetts and the sits at the heart of Tolland State Forest. There is a campground here located by the beach parking area, a sandy swimming area, picnic tables with grills, a public boat ramp, and access to miles of trails.
Skiing
Downhill Skiing
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Cross Country Skiing
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Stump Sprouts Ski Touring Centre
Theater
Shakespeare & Company
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70 Kemble St
Lenox, MA
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Shakespeare that is fun to watch and listen to in a wonderful setting. Sunday they often have discount tickets for students and families.
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6 East St
Stockbridge, MA
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Berkshire Theatre Group’s supports wide ranging artistic exploration and acclaimed performances in theatre, dance, music and entertainment.
Barrington Stage Company
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30 Union St
Pittsfield, MA
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Barrington Stage and Co is located in downtown Pittsfield and puts on some really great plays and musicals.
Phoenix Theatres Beacon Cinema
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57 North St
Pittsfield, MA
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A great alternative to the mall; the Beacon in Pittsfield always runs great movies with good popcorn and very comfortable stadium seats. You can get a glass of wine too if you want. Grab a bite at Marketplace Cafe or Hot Harry's next door.
Jacob's Pillow
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358 George Carter Rd
Becket, MA
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Jacob’s Pillow is lauded worldwide as a “hub and mecca of dancing” (TIME Magazine), “one of America’s most precious cultural assets” (Mikhail Baryshnikov), and “the dance center of the nation” (The New York Times). “The Pillow” is a treasured 220-acre National Historic Landmark, a recipient of the prestigious National Medal of Arts, and home to America’s longest-running international dance festival.
Shopping
Lee Premium Outlets
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17 Premium Outlet Boulevard
Lee, MA
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A shopping destination with 60 stores in the beautiful Berkshires, is designed to mirror an outdoor, quaint New England village. You name it, they have it! Excellent shopping Center with great deals!
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26 Housatonic St
Lenox, MA
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Home good design store for items that are "simple, beautiful and useful."
One Mercantile
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8 Castle St
Great Barrington, MA
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Amazing Lifestyle Store. Great objects and Gifts for any occasion.
Hammertown
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15 Bridge St
Great Barrington, MA
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Nicely curated selection of furniture and accessories.
Tom's Toys
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297 Main St
Great Barrington, MA
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Sweet local toy shop with unique toys and gifts.
Westerlind
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41 Main St
Millerton, NY
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It is always fun to look through this select shop - it offers unique and stylish outdoor-related clothing and home goods. The downstairs has a pantry - you can find some rare items here.
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Spa
Kripalu Center For Yoga & Health
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57 Interlaken Rd
Stockbridge, MA
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A world-renowned health and yoga retreat offering in person and online programs and workshop geared towards restoring the body, spirit and mind.
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165 Kemble St
Lenox, MA
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Canyon Ranch is your haven for an inspiring, healthy getaway. Have fun exploring mind-body wellness opportunities to help you feel your best for life!
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Michele's Salon & Day Spa
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54 Stockbridge Rd
Great Barrington, MA
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Tranquil Spa. Services: Wax Treatments, Hair Design, Makeup, Hands and Feet, Complete Spa Packages, Body Treatments, Body Therapies, Cosmetics, Bridal Services.
Miraval Berkshires
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55 Lee Rd
Lenox, MA
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Another gilded age “cottage”, once known as “Cranwell”, is now home to the premier Miraval wellness center and spa. Offering daily activities, yoga and fitness, mindfulness retreats, spa treatments and more.
Food
Bartlett's Orchard
575 Swamp Rd
Richmond, MA
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Apple picking and fresh cider doughnuts! Worth a stop if you are looking for some local foods or edible gifts to take home with you, and especially if you are heading to West Stockbridge - despite it's unappealing name, Swamp Road is stunning!
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535 Summer St
Lee, MA
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A great local gem! Working cow/dairy farm with processing plant, creamery & farmstand. Also great for kids, delicious ice cream, beautiful setting and lots of cows!
Loeb's Foodtown of Lenox
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42 Main St
Lenox, MA
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Local grocery conveniently located in historic downtown Lenox, Loeb's offers you a friendly atmosphere, wide variety of gourmet foods, and top of the line Deli selections.
Methuselah Bar and Lounge
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391 North St, Pittsfield, MA 01201
Rustic-chic eatery & lounge serving organic wines & craft beer paired with local New American fare.
Frankie's
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80 Main St
Lenox, MA
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At the core of Frankie’s is family + delicious true Italian-American food. Outside dining, take out + vegan options. They pride themselves in making everything fresh using quality ingredients from local farms and businesses. Open every day for dinner only - sister restaurant to Boema Pizza (and next door)
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New Marlborough, MA
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This place is truly a step back in time. Well curated french style cuisine served in an old inn setting where candles are the only light inside the space. Not a better spot around for a romantic date night with a loved one.
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34 Church St
Lenox, MA
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Fabulous French-foodie-owned and managed restaurant and wine bar. Elegant presentation, good service, fresh farm to table ingredients. lunch or dinner. WORTH the drive!
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47 Railroad St
Great Barrington, MA
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Upscale craft cocktail bar on railroad street. Outdoor tables in the summer! Same owners as Cantina 229 restaurant & bar.
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485 Main St
Great Barrington, MA
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Delicious, authentic Indian food. The owners take great pride in insuring you enjoy your meal. It is truly a wonderful dining experience and so delicious.
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31 Main St
Stockbridge, MA
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French-inspired cafe & patisserie serving coffee, tea, pastries and more.
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53 Main St
Egremont, MA
South Egremont
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The building itself is amazing and old. Food is great and hospitality amazing. They have a cute bar that is locked in the 1700s. Great spot for a romantic dinner.
District Kitchen & Bar
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40 West St
Pittsfield, MA
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Fancier upscale dining with great food and a fantastic cocktail bar. Great place for a date or even a solo glass of wine if you're in town by yourself.
Marketplace Kitchen Table
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240 Stockbridge Rd
Great Barrington, MA
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Great breakfasts and lunch. Dinner now served in the Great Barrington restaurant. Homemade baked goods, outstanding soups, salads, wraps & sandwiches.
Starving Artist Creperie and Cafe
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40 Main St
Lee, MA
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Great food, lots of healthy options including vegan and gluten-free. Some of the seating is in a bright and airy art gallery. On main street in Lee.
Cafe Adam Bar and Restaurant
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420 Stockbridge Rd
Great Barrington, MA
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Special-occasion restaurant offering New American dishes in a bustling, rustic-chic atmosphere.
Bizen Gourmet Japanese Restaurant and Sushi Bar
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17 Railroad Street
Great Barrington, MA
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Best Sushi in town, with lots of vegan and vegetarian sushi as well. Great healthy salads, grilled fish, chicken and tempura.
Agaves Mexican Grill
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389 Stockbridge Rd
Great Barrington, MA
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Fresh and tasty Mexican menu. Friendly staff. Indoor & outdoor seating as well as take out.
Pizzeria Boema
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84 Main St
Lenox, MA
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Delicious brick oven pizza with ample indoor and outdoor dining (their is a rustic barn in the back area). Arrive early or make a reservation a head of time as this place gets pretty busy. Open for both lunch and dinner. Closed on Mondays.
Marjoram + Roux
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Great Barrington, MA
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Beautiful breakfast/lunch restaurant in downtown Great Barrington. Nice environment and decor. Most impressive is the food; unique and delicious sandwiches with different specials that change regularly. A little pricey but well worth it. Try the roast beef with caraway mayo or the pastrami. Good coffee too. Best lunch place in town.
Once Upon a Table
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36 Main St
Stockbridge, MA
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A small and pretty wonderful European style bistro featuring continental cuisine. They have some outdoor tables too, in the cozy alley in which they're located in downtown Stockbridge.
Baba Louie's Sourdough Pizza
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42/44 Railroad St
Great Barrington, MA
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It's hard to experience Great Barrington without going to Baba Louie's. Even if you are gluten and dairy free you still can get that pizza buzz. Great thin crust pizzas and great salads. Kid friendly.
GB Eats
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282 Main St
Great Barrington, MA
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Great diner. Also great breakfast and brunch fare. Wonderful menu and cozy atmosphere.
Otis Poultry Farm
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1570 N Main Rd
Otis, MA
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A wonderful stop for toys, wines, specialty foods, fresh produce and groceries
Brava
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65 Church St
Lenox, MA
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Wine & beer bar offering bites such as pizza, cheese & charcuterie in intimate surrounds.
Nejaime's Wine Cellars
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Dare Bottleshop & Provisions
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Lenox, MA
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Nice wine,cold beer,craft cider. Specialty foods,events,supper club. Your dinner party, real wine destination.
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