Guidebook for Berkshire County
Food Scene
Sweet, cozy atmosphere. One of our favorite breakfast/lunch places.
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Haven
8 Franklin StSweet, cozy atmosphere. One of our favorite breakfast/lunch places.
Our favorite restaurant. Five minutes from the farmhouse. It's in an old Victorian house and the food is glorious. "Pub food with a twist"- they describe it.
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51 Park Restaurant & Tavern
51 Park StOur favorite restaurant. Five minutes from the farmhouse. It's in an old Victorian house and the food is glorious. "Pub food with a twist"- they describe it.
Part of Guido's Fresh Marketplace in Pittsfield. This cafe specializes in fresh smoothies with house-made nut milks (seriously the best) and locally sourced espresso beverages. Best smoothies around.
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Guido's Cafe
1020 Pittsfield RdPart of Guido's Fresh Marketplace in Pittsfield. This cafe specializes in fresh smoothies with house-made nut milks (seriously the best) and locally sourced espresso beverages. Best smoothies around.
Cool, eclectic, spacious atmosphere. They serve locally sourced food & coffee beverages. Definitely a staple of Pittsfield food/coffee culture.
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Dotties Coffee Lounge
444 North StCool, eclectic, spacious atmosphere. They serve locally sourced food & coffee beverages. Definitely a staple of Pittsfield food/coffee culture.
Yummy ice cream, many flavor options. A short drive from the Air BNB.
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Lucky's Ice Cream & Grill
30 W Center StYummy ice cream, many flavor options. A short drive from the Air BNB.
Really popular pizza shop, but they also serve other food. They source quality ingredients. Our favorite pizza. A short drive from the Air BNB.
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Betty's Pizza Shack
26 Housatonic StReally popular pizza shop, but they also serve other food. They source quality ingredients. Our favorite pizza. A short drive from the Air BNB.
Relaxed, locally focused American eatery for crepes, panini & coffee, plus gluten-free & vegan fare. Located in downtown Lee, a short drive from the Air BNB.
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Starving Artist Creperie and Cafe
40 Main StRelaxed, locally focused American eatery for crepes, panini & coffee, plus gluten-free & vegan fare. Located in downtown Lee, a short drive from the Air BNB.
Barrington Brewery & Restaurant
420 Stockbridge RoadThe Bistro Box
937 S Main StThe Prairie Whale
178 Main StOlde Forge Restaurant
125 N Main StWell known for their chicken wings.
Bistro Zinc
56 Church StTrattoria Rustica
27 Mc Kay StItalian fare. Some of the best around (we think).
Believe it or not, Norman Rockwell based his famous painting “The Runaway” within this diner. Been around for decades. Good classic diner breakfast food. In downtown Lee, close to farmhouse.
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Joe's Diner
85 Center StBelieve it or not, Norman Rockwell based his famous painting “The Runaway” within this diner. Been around for decades. Good classic diner breakfast food. In downtown Lee, close to farmhouse.
Parks & Nature
We (and our dog) love Kennedy Park. There are trails for every ability level. Park at the Arcadian Shop, grab a trail map from the shop, and meander down Woolsey (the main, wide, carriage trail that runs through the center of Kennedy Park). Go in the morning, walk through the fog, and whistle along with the birds above you. 500+ acres of well marked, intersecting trails.
Kennedy Park - Access
91 Pittsfield RdWe (and our dog) love Kennedy Park. There are trails for every ability level. Park at the Arcadian Shop, grab a trail map from the shop, and meander down Woolsey (the main, wide, carriage trail that runs through the center of Kennedy Park). Go in the morning, walk through the fog, and whistle along with the birds above you. 500+ acres of well marked, intersecting trails.
The farmhouse is essentially at the bottom of October Mountain State Forest. Follow our road to the left, and you'll wind up at the campground. In the summer, there's camping and hiking. In the winter, there's snowshoeing and cross country skiing. There are trail maps at the service building.
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October Mountain State Forest
317 Woodland RoadThe farmhouse is essentially at the bottom of October Mountain State Forest. Follow our road to the left, and you'll wind up at the campground. In the summer, there's camping and hiking. In the winter, there's snowshoeing and cross country skiing. There are trail maps at the service building.
Mt. Greylock is the highest peak in Massachusetts! From the top, you can look into 5 states: Vermont, New Hampshire, Connecticut, New York, & Massachusetts (of course). You can drive all the way to the summit from Lanesborough. There's also many hiking trails with many different access points. Worth seeing on a sunny, clear day.
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Mount Greylock State Reservation
30 Rockwell RdMt. Greylock is the highest peak in Massachusetts! From the top, you can look into 5 states: Vermont, New Hampshire, Connecticut, New York, & Massachusetts (of course). You can drive all the way to the summit from Lanesborough. There's also many hiking trails with many different access points. Worth seeing on a sunny, clear day.
Monument Mountain is a very popular Berkshire hiking trail. The trail offers three loop trails- none longer than three miles. Great views from the top, interesting geology/rock formations, and a literary history.
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Monument Mountain Reservation
Monument Mountain is a very popular Berkshire hiking trail. The trail offers three loop trails- none longer than three miles. Great views from the top, interesting geology/rock formations, and a literary history.
Beautiful walking area. Mostly flat, for easy, accessible meandering. You may see lots of aerial wildlife here. You can walk around the pond, through marshes, through fields, and in the woods.
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Mass Audubon Canoe Meadows Wildlife Sanctuary
309 Holmes RdBeautiful walking area. Mostly flat, for easy, accessible meandering. You may see lots of aerial wildlife here. You can walk around the pond, through marshes, through fields, and in the woods.
Marshy and nice. Boardwalks to follow. Good for families.
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Mass Audubon's Pleasant Valley Wildlife Sanctuary
472 W Mountain RdMarshy and nice. Boardwalks to follow. Good for families.
Wild Acres Park
South Mountain RoadIn Pittsfield.
Very popular location for people visiting Berkshire County. There’s hiking trails off of the overlook.
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Olivia's Overlook
Hiking TrailsVery popular location for people visiting Berkshire County. There’s hiking trails off of the overlook.
Very popular hiking trail in Berkshire County. Beautiful features.
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Ice Glen Trail
Ice Glen TrailVery popular hiking trail in Berkshire County. Beautiful features.
A bit of a drive from the farmhouse, but a beautiful hike leading to a waterfall on Mt. Greylock. Not the easiest.
Money Brook Falls Trailhead
Notch RoadA bit of a drive from the farmhouse, but a beautiful hike leading to a waterfall on Mt. Greylock. Not the easiest.
Another popular hiking area in the Berkshires.
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Tyringham Cobble Park
20 Jerusalem RdAnother popular hiking area in the Berkshires.
Absolutely beautiful look out over the mountains & lakes at the top. Not too bad of a hike for the view you get.
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The Cobbles
Absolutely beautiful look out over the mountains & lakes at the top. Not too bad of a hike for the view you get.
Lots of hiking trails here. Very beautiful location.
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Pittsfield State Forest
1041 Cascade StLots of hiking trails here. Very beautiful location.
Shopping
This shop is beautiful and inspiring. They offer high-end, gorgeous outdoor clothing and gear. On one side, there is a little cafe and bookstore. You can access Kennedy Park hiking trails from the parking lot.
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Arcadian Shop
91 Pittsfield RdThis shop is beautiful and inspiring. They offer high-end, gorgeous outdoor clothing and gear. On one side, there is a little cafe and bookstore. You can access Kennedy Park hiking trails from the parking lot.
I love this little shop! They have the prettiest, most unique, & whimsical home goods. Every item in this store has been chosen with intention and is of high aesthetic. A wonderful boutique.
Dory & Ginger
299 North StI love this little shop! They have the prettiest, most unique, & whimsical home goods. Every item in this store has been chosen with intention and is of high aesthetic. A wonderful boutique.
Guido's is a family owned natural foods store with something for everyone. They have many gluten-free options and many vegan options, along with many other food options. They serve pizza, sandwiches, and packaged food in the deli. They have a beautiful home goods and floral section called Bella Flora. They have a corner completely dedicated to cheese! There is a smoothie and espresso cafe as well. There is a Pittsfield and a Great Barrington location. A staple in our Berkshire County community.
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Guido's Fresh Marketplace
760 S Main StGuido's is a family owned natural foods store with something for everyone. They have many gluten-free options and many vegan options, along with many other food options. They serve pizza, sandwiches, and packaged food in the deli. They have a beautiful home goods and floral section called Bella Flora. They have a corner completely dedicated to cheese! There is a smoothie and espresso cafe as well. There is a Pittsfield and a Great Barrington location. A staple in our Berkshire County community.
My favorite antique shop. Located in downtown Lee, only a short drive from the Air BNB. So much to look at.
Finders Keepers
53 Main StMy favorite antique shop. Located in downtown Lee, only a short drive from the Air BNB. So much to look at.
Premier shopping destination in the Berkshires, 60+ outlets. Short drive from the Air BNB.
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Lee Premium Outlets
17 Premium Outlet BoulevardPremier shopping destination in the Berkshires, 60+ outlets. Short drive from the Air BNB.
Route 7 Trading Post
55 Pittsfield RdAnother antique shop of sorts.
Berkshire Mantiques
20 Williamstown RdAn antique shop of sorts.
Arts & Culture
Norman Rockwell- one of the most iconic American painters. Art enthusiasts must visit. Visit ww.nrm.org to view current exhibits.
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Muzium Norman Rockwell
9 Glendale RdNorman Rockwell- one of the most iconic American painters. Art enthusiasts must visit. Visit ww.nrm.org to view current exhibits.
Hundreds of paintings from world-famous artists, beautiful grounds, stunning architecture, and rotating exhibits. This place is well known and worth visiting for a day. Visit https://www.clarkart.edu/ for more information.
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The Clark Art Institute
225 South StHundreds of paintings from world-famous artists, beautiful grounds, stunning architecture, and rotating exhibits. This place is well known and worth visiting for a day. Visit https://www.clarkart.edu/ for more information.
Celebrated museum & performing arts center highlighting the work of contemporary artists since 1999. If you enjoy eccentric pieces and contemporary art, this is the place for you. All of your senses will be engaged. Visit https://massmoca.org/ for more information.
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MASS MoCA
1040 Mass MoCA WayCelebrated museum & performing arts center highlighting the work of contemporary artists since 1999. If you enjoy eccentric pieces and contemporary art, this is the place for you. All of your senses will be engaged. Visit https://massmoca.org/ for more information.
The summer home and music venue of the Boston Symphony Orchestra since 1937. Tanglewood is an important piece of South County Berkshire culture. Many famous composers and modern day artists preform here. Bring your wine, cheese platters, finger foods, and prepare for a musical night under the stars. Visit https://www.bso.org/ for more information.
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Tanglewood
The summer home and music venue of the Boston Symphony Orchestra since 1937. Tanglewood is an important piece of South County Berkshire culture. Many famous composers and modern day artists preform here. Bring your wine, cheese platters, finger foods, and prepare for a musical night under the stars. Visit https://www.bso.org/ for more information.
Jacob's Pillow is a dance center, school and performance space. The organization is known for the oldest internationally acclaimed Summer dance festival in the United States. Visit https://www.jacobspillow.org for more information.
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Jacob's Pillow
358 George Carter RdJacob's Pillow is a dance center, school and performance space. The organization is known for the oldest internationally acclaimed Summer dance festival in the United States. Visit https://www.jacobspillow.org for more information.
Home of famous author, Herman Melville, from 1850-1863. Dedicated to preserving the history of Berkshire County and the Arrowhead Farm. Explore the historical house museum and the surrounding grounds.
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Arrowhead Museum
780 Holmes RdHome of famous author, Herman Melville, from 1850-1863. Dedicated to preserving the history of Berkshire County and the Arrowhead Farm. Explore the historical house museum and the surrounding grounds.
Essentials
Only a short drive from our house. You can get all of your needs here. Stop before arriving- as it is just off of the Mass Pike.
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Big Y World Class Market
10 Pleasant StOnly a short drive from our house. You can get all of your needs here. Stop before arriving- as it is just off of the Mass Pike.
CVS
107 West StRite Aid
21 Columbia StStop & Shop
876 State RdDrinks & Nightlife
Rustic-chic tapas bar with loungy vibe features Spanish small plates, Iberian wines & live musicians.
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Mission
438 North StRustic-chic tapas bar with loungy vibe features Spanish small plates, Iberian wines & live musicians.
Rustic-chic eatery & lounge serving organic wines & craft beer paired with local New American fare.
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Methuselah
391 North StreetRustic-chic eatery & lounge serving organic wines & craft beer paired with local New American fare.
Many refer to this place as "the best beer joint in the Berkshires." They also serve food.
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Thistle & Mirth
44 West StMany refer to this place as "the best beer joint in the Berkshires." They also serve food.
Entertainment & Activities
An aerial, tree-to-tree adventure park set amongst pristine New England forest. Thrill seeker or not- the adventure park is welcome to all fitness levels and experience levels. There are beginner to advanced trails. My husband and I made some of our sweetest memories here! Get out of your comfort zone, breathe in the mountain air, and have some fitness fun! Very family friendly. Visit http://ramblewild.com/index.php for more information and pricing.
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Ramblewild Adventure Park
110 Brodie Mountain RdAn aerial, tree-to-tree adventure park set amongst pristine New England forest. Thrill seeker or not- the adventure park is welcome to all fitness levels and experience levels. There are beginner to advanced trails. My husband and I made some of our sweetest memories here! Get out of your comfort zone, breathe in the mountain air, and have some fitness fun! Very family friendly. Visit http://ramblewild.com/index.php for more information and pricing.
Naumkeag is a public garden and historic home in the heart of the Berkshires, Massachusetts. Experience Gilded Age style and splendor at this marvelous estate renowned for its elegant gardens and rare Berkshire “cottage.” Explore the grounds and/or the historical home.
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Naumkeag
5 Prospect Hill RdNaumkeag is a public garden and historic home in the heart of the Berkshires, Massachusetts. Experience Gilded Age style and splendor at this marvelous estate renowned for its elegant gardens and rare Berkshire “cottage.” Explore the grounds and/or the historical home.
Jiminy Peak
37 Corey RdBousquet Ski Area
101 Dan Fox DrSki Butternut
380 State RdHancock Shaker Village
1843 W Housatonic StIoka Valley Farm
3475 Hancock RoadHigh Lawn Farm
535 Summer StMini-golf. Crispy Cones Icecream/Soft serve/food place is right down the street, too.
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Baker's Golf Center
633 S Main StMini-golf. Crispy Cones Icecream/Soft serve/food place is right down the street, too.