Beautiful Berkshires - Chelsea's Tips & Tricks

Chelsea
Beautiful Berkshires - Chelsea's Tips & Tricks

City/town information

Stockbridge has it all: an historic downtown, shops, gilded mansions and grounds, lakes, hiking, and botanical gardens. Stockbridge's Main Street welcomes visitors with its small shops, country store, eateries and galleries, with the historic Red Lion Inn and its wrap-around porch headlining among the places to stop. For the Art Lovers: Norman Rockwell Museum: artist's museum, studio & grounds; Chesterwood, the artist's historic home, studio and gardens, mountain views. For the Historian: Naumekeag: gilded-age 44 room "Cottage" (in Berkshires speak, "cottages" often mean historic mansions!) with stunning grounds. For Floral Friends: Berkshires Botanical Gardens' 24 acres feature dozens of display areas emphasizing plants that are native to the Northeast. It also has a lovely children's garden. For Hikers: Olivia's Overlook, a popular overlook and trailhead for 6 miles of trail providing top-notch views. Monument Mountain Summit: a 3.8 mile out and back trail located a few miles north of Great Barrington (and a few miles south of Stockbridge).
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Stockbridge
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Stockbridge has it all: an historic downtown, shops, gilded mansions and grounds, lakes, hiking, and botanical gardens. Stockbridge's Main Street welcomes visitors with its small shops, country store, eateries and galleries, with the historic Red Lion Inn and its wrap-around porch headlining among the places to stop. For the Art Lovers: Norman Rockwell Museum: artist's museum, studio & grounds; Chesterwood, the artist's historic home, studio and gardens, mountain views. For the Historian: Naumekeag: gilded-age 44 room "Cottage" (in Berkshires speak, "cottages" often mean historic mansions!) with stunning grounds. For Floral Friends: Berkshires Botanical Gardens' 24 acres feature dozens of display areas emphasizing plants that are native to the Northeast. It also has a lovely children's garden. For Hikers: Olivia's Overlook, a popular overlook and trailhead for 6 miles of trail providing top-notch views. Monument Mountain Summit: a 3.8 mile out and back trail located a few miles north of Great Barrington (and a few miles south of Stockbridge).
Lenox is home to culture, dining, shops, historic mansions and nature. Just a few minutes drive from our cottage, you will find yourself in downtown Lenox. It is comprised of several pedestrian-friendly streets with fine and casual dining, ice cream shops, breakfast shops, art galleries and the like. For the Culturists: Within just a few minutes drive, you can arrive at Shakespeare & Company, the performing arts center. Tanglewood, the beautiful grounds and summer home of the Boston Symphony Orchestra. Kripalu, a renowned yoga and wellness center. (Both Tanglewood and Kripalu are each visible by looking straight across the Stockbridge Bowl (lake) from our cottage's community lake access point. ) For the Literati: consider the Mount, a turn-of-the-century home, designed, built and lived in by writer Edith Wharton which is a National Historic Landmark. For the nature-lovers: Mass Audubon Society: varied trails winding through forests, meadows, wetlands. Kennedy Park, containing nearly 15 miles of groomed trails, ideal for hiking, picnics and mountain views, small wildlife creatures (frogs, birds)
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Lenox
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Lenox is home to culture, dining, shops, historic mansions and nature. Just a few minutes drive from our cottage, you will find yourself in downtown Lenox. It is comprised of several pedestrian-friendly streets with fine and casual dining, ice cream shops, breakfast shops, art galleries and the like. For the Culturists: Within just a few minutes drive, you can arrive at Shakespeare & Company, the performing arts center. Tanglewood, the beautiful grounds and summer home of the Boston Symphony Orchestra. Kripalu, a renowned yoga and wellness center. (Both Tanglewood and Kripalu are each visible by looking straight across the Stockbridge Bowl (lake) from our cottage's community lake access point. ) For the Literati: consider the Mount, a turn-of-the-century home, designed, built and lived in by writer Edith Wharton which is a National Historic Landmark. For the nature-lovers: Mass Audubon Society: varied trails winding through forests, meadows, wetlands. Kennedy Park, containing nearly 15 miles of groomed trails, ideal for hiking, picnics and mountain views, small wildlife creatures (frogs, birds)
Downtown Great Barrington Cultural District is home to great restaurants, unique shops, visual arts, historic and heritage venues. For the Shoppers: Various boutiques, clothing/apparel, children’s apparel, and home furnishing shops. For the Fruit Pickers: Visit WIndy Hill Farms in the summer to pick-your-own blueberries, or in the fall to pick-your-own apples. For the Hiker: The Monument Mountain Summit is a 3.8 mile out and back trail located a few miles north of Great Barrington . Foodies: Looking for gourmet food to prepare a nice meal? Look no further than Guido's Fresh Marketplace (there is another location in Pittsfield). They also sell frozen pizzas by Great Barrington's own Babalouie's flagship of a small chain of wood-fired pizzas restaurants known for its sourdough crusts and gourmet toppings.
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Great Barrington
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Downtown Great Barrington Cultural District is home to great restaurants, unique shops, visual arts, historic and heritage venues. For the Shoppers: Various boutiques, clothing/apparel, children’s apparel, and home furnishing shops. For the Fruit Pickers: Visit WIndy Hill Farms in the summer to pick-your-own blueberries, or in the fall to pick-your-own apples. For the Hiker: The Monument Mountain Summit is a 3.8 mile out and back trail located a few miles north of Great Barrington . Foodies: Looking for gourmet food to prepare a nice meal? Look no further than Guido's Fresh Marketplace (there is another location in Pittsfield). They also sell frozen pizzas by Great Barrington's own Babalouie's flagship of a small chain of wood-fired pizzas restaurants known for its sourdough crusts and gourmet toppings.

Museum/Grounds

In Stockbridge, you can visit the famous Norman Rockwell museum and its amazing grounds. Visit the artist's own studio. Located on 36-acres, overlooking the Housatonic River Valley, the Norman Rockwell Museum illuminates the power of American illustration art to reflect and shape society, and advances the enduring values of kindness, respect, and social equity portrayed by Norman Rockwell, who worked and lived in Stockbridge. Walk the grounds to see outdoor sculptures. Great on-site café. https://www.nrm.org/
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Norman Rockwell Museum
9 Glendale Road
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In Stockbridge, you can visit the famous Norman Rockwell museum and its amazing grounds. Visit the artist's own studio. Located on 36-acres, overlooking the Housatonic River Valley, the Norman Rockwell Museum illuminates the power of American illustration art to reflect and shape society, and advances the enduring values of kindness, respect, and social equity portrayed by Norman Rockwell, who worked and lived in Stockbridge. Walk the grounds to see outdoor sculptures. Great on-site café. https://www.nrm.org/
North Adams - Mass MOCA (Museum of Contemporary Arts) https://massmoca.org/ (North Adams is appx 45 min drive.) Vast galleries and a stunning collection of indoor and outdoor performing arts venues, it embraces all forms of art: music, sculpture, dance, film, painting, photography, theater, and new, boundary-crossing works of art. Works are shown in light-filled spaces, and within a lovely network of late 19th-century courtyards. Advance, timed tickets are recommended. On-site café.
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MASS MoCA
1040 Mass MoCA Way
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North Adams - Mass MOCA (Museum of Contemporary Arts) https://massmoca.org/ (North Adams is appx 45 min drive.) Vast galleries and a stunning collection of indoor and outdoor performing arts venues, it embraces all forms of art: music, sculpture, dance, film, painting, photography, theater, and new, boundary-crossing works of art. Works are shown in light-filled spaces, and within a lovely network of late 19th-century courtyards. Advance, timed tickets are recommended. On-site café.
In Stockbridge, you can tour the historic home, studio and gardens of America’s foremost 20th century, sculptor: Daniel Chester French who created the Lincoln Memorial. Tour the house, gardens and lovely mountain views. https://www.chesterwood.org/
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Chesterwood
3 Williamsville Road
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In Stockbridge, you can tour the historic home, studio and gardens of America’s foremost 20th century, sculptor: Daniel Chester French who created the Lincoln Memorial. Tour the house, gardens and lovely mountain views. https://www.chesterwood.org/
In Lenox, you can visit this turn-of-the-century home, designed, built and lived in by writer Edith Wharton in 1902. A National Historic Landmark, today The Mount is a cultural center that celebrates the intellectual, artistic and humanitarian legacy of Edith Wharton. You can tour the house (with a tour/fee). The formal gardens and grounds are open for public use unless otherwise posted. https://www.edithwharton.org/ (Lenox)
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The Mount, Edith Wharton's Home
2 Plunkett Street
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In Lenox, you can visit this turn-of-the-century home, designed, built and lived in by writer Edith Wharton in 1902. A National Historic Landmark, today The Mount is a cultural center that celebrates the intellectual, artistic and humanitarian legacy of Edith Wharton. You can tour the house (with a tour/fee). The formal gardens and grounds are open for public use unless otherwise posted. https://www.edithwharton.org/ (Lenox)
In Stockbridge, visit the former private home of 44-room shingle-style home, complete with formal gardens may be toured (pre-purchasing tickets recommended), which seasonal events are now held, is a prime example of the Gilded Age Berkshire “Cottages”. Explore the famous gardens which transform into a celebration of autumn with over 1,500 jack-o-lanterns, hundreds of mums, pumpkins and countless gourds – most of which were grown right here at Naumkeag! Check website for ticketing. Naumkeag https://thetrustees.org/place/naumkeag/
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Naumkeag
5 Prospect Hill Road
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In Stockbridge, visit the former private home of 44-room shingle-style home, complete with formal gardens may be toured (pre-purchasing tickets recommended), which seasonal events are now held, is a prime example of the Gilded Age Berkshire “Cottages”. Explore the famous gardens which transform into a celebration of autumn with over 1,500 jack-o-lanterns, hundreds of mums, pumpkins and countless gourds – most of which were grown right here at Naumkeag! Check website for ticketing. Naumkeag https://thetrustees.org/place/naumkeag/
Considering stopping to "smell the roses" at the Berkshires Botanical Gardens' 24 acres feature dozens of display areas that are educational, functional, and highly ornamental, with plant collections emphasizing plants that are native to the Northeast. It also has a lovely children's garden and family friendly programming.
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Berkshire Botanical Garden
5 East Stockbridge Lee Road
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Considering stopping to "smell the roses" at the Berkshires Botanical Gardens' 24 acres feature dozens of display areas that are educational, functional, and highly ornamental, with plant collections emphasizing plants that are native to the Northeast. It also has a lovely children's garden and family friendly programming.

Outdoor Cultural Point of Interest

Summer home of the Boston Symphony Orchestra, also great concerts by the Boston Pops, and other high-quality musicians. The “Shed” is for ticketing seating, while traditionally the “Lawn” (also requires tickets) is where you will find varied levels of picnicking, from very basic to elaborate displays. If you go to Tanglewood, bring chairs or rent them at Tanglewood. There is also food available on-site. Must check calendar for list of performances and ticketing. Located appx 5 minutes by car, and is located on the north side of the Stockbridge Bowl. A visit to the grounds, even without a performance, provides foliage, mountain and lake views.
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Tanglewood
297 West Street
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Summer home of the Boston Symphony Orchestra, also great concerts by the Boston Pops, and other high-quality musicians. The “Shed” is for ticketing seating, while traditionally the “Lawn” (also requires tickets) is where you will find varied levels of picnicking, from very basic to elaborate displays. If you go to Tanglewood, bring chairs or rent them at Tanglewood. There is also food available on-site. Must check calendar for list of performances and ticketing. Located appx 5 minutes by car, and is located on the north side of the Stockbridge Bowl. A visit to the grounds, even without a performance, provides foliage, mountain and lake views.

Performance Arts Center

Shakespeare & Co. https://www.shakespeare.org/ Performing arts center of creative and collaborative excellence, rooted in Shakespeare’s work and the Elizabethan ideals of inquiry, balance and harmony. Check website for events and pre-purchasing tickets.
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Shakespeare & Company
70 Kemble Street
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Shakespeare & Co. https://www.shakespeare.org/ Performing arts center of creative and collaborative excellence, rooted in Shakespeare’s work and the Elizabethan ideals of inquiry, balance and harmony. Check website for events and pre-purchasing tickets.
Jacob’s Pillow. professional dance troupes visit throughout the summer at this beautiful setting, located in Becket Appx 30 min drive. Check website for event schedule and pre-purchasing tickets. In normal seasons, there is fine dining and a casual, but tasty take out sandwiches, and beer/wine. Various picnic tables are around this vast property.
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Jacob's Pillow
358 George Carter Road
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Jacob’s Pillow. professional dance troupes visit throughout the summer at this beautiful setting, located in Becket Appx 30 min drive. Check website for event schedule and pre-purchasing tickets. In normal seasons, there is fine dining and a casual, but tasty take out sandwiches, and beer/wine. Various picnic tables are around this vast property.

Food scene

Highlawn Farm. https://www.highlawnfarm.com/ Family-owned, Jersey dairy farm producing creamery products including farm-fresh milk & cream, chocolate milk, slow-churned and herb-infused butter varieties, cultured ghee, artisan cheese, and premium ice cream. You can visit the calves (seasonal) and dairy cows and enjoy their amazing ice cream on-site at one of the picnic tables as the Jersey cattle herd grazes in the nearby fields, and mountain views.
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High Lawn Farm
535 Summer Street
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Highlawn Farm. https://www.highlawnfarm.com/ Family-owned, Jersey dairy farm producing creamery products including farm-fresh milk & cream, chocolate milk, slow-churned and herb-infused butter varieties, cultured ghee, artisan cheese, and premium ice cream. You can visit the calves (seasonal) and dairy cows and enjoy their amazing ice cream on-site at one of the picnic tables as the Jersey cattle herd grazes in the nearby fields, and mountain views.
Balderdash Cellars –https://balderdashcellars.com/about/ Boutique winery focused wines from grapes grown by world-class California vineyards, but other wine and beer are available onsite and various food trucks are scheduled. Give a call over to check whether reservations will be taken and for specific events that may result in closures. There is a limited number of tables and available on a first come, first served basis but you are welcome to bring your own.
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Balderdash Cellars
502 East St
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Balderdash Cellars –https://balderdashcellars.com/about/ Boutique winery focused wines from grapes grown by world-class California vineyards, but other wine and beer are available onsite and various food trucks are scheduled. Give a call over to check whether reservations will be taken and for specific events that may result in closures. There is a limited number of tables and available on a first come, first served basis but you are welcome to bring your own.
Apple picking through Columbus Day weekend. Fresh Apple Cider, Cider Donuts, assorted baked goods. www.bartlettsorchard.com
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Bartlett's Orchard
575 Swamp Road
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Apple picking through Columbus Day weekend. Fresh Apple Cider, Cider Donuts, assorted baked goods. www.bartlettsorchard.com

Hiking

The trailhead for 6 miles of trail providing views of Monument Mountain, the Stockbridge Bowl and wildflowers along the way. Listen closely, as this is a favorable habitat for barred owls. It is a popular overlook where you can bring a small picnic.
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Olivia's Overlook
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The trailhead for 6 miles of trail providing views of Monument Mountain, the Stockbridge Bowl and wildflowers along the way. Listen closely, as this is a favorable habitat for barred owls. It is a popular overlook where you can bring a small picnic.
Monument Mountain Summit is a 3.8 mile lightly trafficked out and back trail located a few miles north of Great Barrington (and a few miles south of Stockbridge). Monument Mountain has been the subject of art and literature since the early 1800s, visited by Melville, Hawthorne and others.
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Monument Mountain
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Monument Mountain Summit is a 3.8 mile lightly trafficked out and back trail located a few miles north of Great Barrington (and a few miles south of Stockbridge). Monument Mountain has been the subject of art and literature since the early 1800s, visited by Melville, Hawthorne and others.
An excellent places to enjoy nature. It has varied trails winding through forests, meadows, wetlands.
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Mass Audubon's Pleasant Valley Wildlife Sanctuary
472 West Mountain Road
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An excellent places to enjoy nature. It has varied trails winding through forests, meadows, wetlands.
Large, groomed trails (former carriage paths) containing nearly 15 miles of trails, ideal for hiking, picnics and mountain views.
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Kennedy Park
275 Main Street
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Large, groomed trails (former carriage paths) containing nearly 15 miles of trails, ideal for hiking, picnics and mountain views.
Located at 20 Jerusalem Road. Tyringham, Massachusetts. Cobble Hill Loop is a 2.1 mile moderate loop trail located near Tyringham, that features beautiful wild flowers . The trail is primarily used for hiking, nature trips, and bird watching and is best used from March until October. Tip: Start the trail by heading to the right and keep any eye out for "Rabbit Rock" - a natural rock formation that looks like a big bunny!
Tyringham Cobble Trail
Located at 20 Jerusalem Road. Tyringham, Massachusetts. Cobble Hill Loop is a 2.1 mile moderate loop trail located near Tyringham, that features beautiful wild flowers . The trail is primarily used for hiking, nature trips, and bird watching and is best used from March until October. Tip: Start the trail by heading to the right and keep any eye out for "Rabbit Rock" - a natural rock formation that looks like a big bunny!

Porady dla podróżnych

Nie przegap

PYO (Pick Your Own) Apples & Pumpkins, Cider & Cider Donuts)

Bartlett’s Orchard (Richmond) https://www.bartlettsorchard.com/ Apple picking through Columbus Day weekend. Fresh Apple Cider, Cider Donuts, assorted baked goods. Windy Hill Farm (Great Barrington) https://windyhillfarminc.com/Pick-your-own operations, both blueberries (July) and apples (beginning late August), on family farm. Hilltop Orchards (Richmond) https://www.hilltoporchards.com/ 100 yr old orchard with views of 3 states. PYO Apples, craft cider, wine, donuts. Ioka Valley Farm (Uncle Don’s Barnyard) (Hancock) PYO favorite pumpkin, colorful corns, Cider Donuts, animal petting area.
Podróżowanie z dziećmi

Dairy farm/Creamery & Views - Highlawn Farm (Lee) -

Visit calves, the dairy cows and have amazing fresh ice cream from those cows’ milk while admiring the view of the grazing meadow and mountains. They also sell “fancy” cheese and other of their own products in the shop attached to the ice creamery.
Podróżowanie z dziećmi

Hancock Shaker Village - Farm animals & demonstrations

A living history museum in the Berkshires Hancock Shaker Village brings the Shaker story to life and preserve it for future generations. Typically, there is a small petting zoo and farm animals. There is a fairly flat loop trail on site. There are picnic tables/picnic areas and a small café. There are special events from time to time – see website for calendar. https://hancockshakervillage.org/
Podróżowanie z dziećmi

Naumkeag - Pumpkin Show

Explore the famous gardens which transform into a celebration of autumn with over 1,500 jack-o-lanterns, hundreds of mums, pumpkins and countless gourds – most of which were grown right here at Naumkeag! Check website for ticketing.