Emily's Guidebook to the Berkshires

Emily
Emily's Guidebook to the Berkshires

Skiing, Snowboarding, and Snow Sports

Ski mountains you can drive to within 30 minutes.
You get discounted tickets on Wednesdays!
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Ski Butternut Tubing Center
380 State Road
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You get discounted tickets on Wednesdays!
Smallest mountain in the area. Recently under new ownership with a lot of updates.
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Bousquet Ski Area
101 Dan Fox Drive
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Smallest mountain in the area. Recently under new ownership with a lot of updates.
The largest mountain in the area.
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Jiminy Peak
37 Corey Road
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The largest mountain in the area.
Steepest slopes in the area. Close to two cozy restaurants - John Andrews and The Old Mill.
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Catamount Ski Area
78 Catamount Road
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Steepest slopes in the area. Close to two cozy restaurants - John Andrews and The Old Mill.

Restaurants

Best restaurants in the area that are 20 minutes or less from the house.
Homemade Italian food. Don't forget to get the clams appetizer!
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Frankie's
80 Main St
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Homemade Italian food. Don't forget to get the clams appetizer!
One of the most historic restaurants in the area. Make sure you get a glass of wine on the porch overlooking Main Street.
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The Red Lion Inn
30 Main Street
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One of the most historic restaurants in the area. Make sure you get a glass of wine on the porch overlooking Main Street.
Great cocktails. Reservations are needed. If you want to sit at the bar, arrive prior to 5:30 pm.
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Alta
34 Church Street
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Great cocktails. Reservations are needed. If you want to sit at the bar, arrive prior to 5:30 pm.
Delicious funky pizza. Same ownership as Frankies Italian Restaurant.
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Pizzeria Boema
84 Main Street
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Delicious funky pizza. Same ownership as Frankies Italian Restaurant.
Best pizza in the county. Hands down.
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Baba Louie's Sourdough Pizza
286 Main Street
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Best pizza in the county. Hands down.
Gourmet Japanese restaurant. If you like spicy, get the Afghani roll!
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Bizen Gourmet Japanese Restaurant and Sushi Bar
17 Railroad Street
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Gourmet Japanese restaurant. If you like spicy, get the Afghani roll!
Coziest restaurant in the area. Excellent food and wine. Friendly ownership. Reservations needed. Very small bar area. You can park at the bank next door.
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Old Mill
53 Main Street
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Coziest restaurant in the area. Excellent food and wine. Friendly ownership. Reservations needed. Very small bar area. You can park at the bank next door.
A hip restaurant. Large bar. First-class cocktails. Muscles are the favorite!
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District Kitchen & Bar
40 West Street
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A hip restaurant. Large bar. First-class cocktails. Muscles are the favorite!
Local friendly bar.
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Michaels of Stockbridge
5 Elm St
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Local friendly bar.
Comfort meals. Reservations needed, perhaps days ahead.
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Cafe Adam, Bar and Restaurant
420 Stockbridge Road
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Comfort meals. Reservations needed, perhaps days ahead.
Great breakfast sandwiches and coffee. Healthy options are abundant.
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No. Six Depot Roastery & Cafe
6 Depot Street
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Great breakfast sandwiches and coffee. Healthy options are abundant.
New York-style bagel shop. Numerous bagel and cream cheese options. Delicious lox. You can order online and pick it up, although we suggest the in-person experience for the first-timers.
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Great Barrington Bagel Company
777 South Main Street
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New York-style bagel shop. Numerous bagel and cream cheese options. Delicious lox. You can order online and pick it up, although we suggest the in-person experience for the first-timers.
Local brewery serving bar and comfort food.
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Barrington Brewery & Restaurant
420 Stockbridge Road
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Local brewery serving bar and comfort food.
Fun family place. Grab an outside table in the summer! Live music, pizza truck on special nights, and more!
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The Prairie Whale
178 Main Street
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Fun family place. Grab an outside table in the summer! Live music, pizza truck on special nights, and more!
Best Mexican food in the area. Family-owned. Margaritas are top-notch.
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Xicohtencatl Restaurant
50 Stockbridge Road
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Best Mexican food in the area. Family-owned. Margaritas are top-notch.

Neighborhoods

Check out Historic Lenox that has many great restaurants and shops.
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Lenox
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Check out Historic Lenox that has many great restaurants and shops.
Vibrant Berkshires town. Enjoy numerous coffee shops, pastry shops, restaurants, stores, and much more. During the summer on Saturdays, check out the local farmers market.
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Great Barrington
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Vibrant Berkshires town. Enjoy numerous coffee shops, pastry shops, restaurants, stores, and much more. During the summer on Saturdays, check out the local farmers market.
Norman Rockwell's hometown. Main Street is in one of his most famous paintings. Recognized as of the most beautiful main streets in America.
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Stockbridge
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Norman Rockwell's hometown. Main Street is in one of his most famous paintings. Recognized as of the most beautiful main streets in America.

Shops

A dream spot for all ages. Every candy you can possibly imagine, from all over the world. Dark chocolate salted caramels are to die for.
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Robin's Candy Shop
288 Main Street
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A dream spot for all ages. Every candy you can possibly imagine, from all over the world. Dark chocolate salted caramels are to die for.
Everything you need for the charcuterie of your dreams.
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Rubiner's Cheesemongers
264 Main Street
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Everything you need for the charcuterie of your dreams.
Great selection of wine.
Nejaime's Wine Cellar
3 Elm St
Great selection of wine.
Most helpful staff in the area. They will answer any question and will even carry your order to your car.
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Domaney's Liquors and Fine Wines
66 Main Street
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Most helpful staff in the area. They will answer any question and will even carry your order to your car.
Well-known bakery. Bread, pastries, pizzas, etc. Grab a jar of the Berkshire Honey Company honey with your bread order!
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Berkshire Mountain Bakery Inc
367 Park Street
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Well-known bakery. Bread, pastries, pizzas, etc. Grab a jar of the Berkshire Honey Company honey with your bread order!
Gourmet chocolate. Enough said.
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Chocolate Springs Cafe
55 Pittsfield Road
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Gourmet chocolate. Enough said.
The best ice cream in the Berkshires. Hands down.
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Soco Creamery
5 Railroad Street
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The best ice cream in the Berkshires. Hands down.

Spa & Relaxation

A well-known luxury spa, famous worldwideSp
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Canyon Ranch Lenox
165 Kemble Street
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A well-known luxury spa, famous worldwideSp
Spa and golf!
Miraval Berkshires
55 Lee Road
Spa and golf!

Activities

One of the most famous (and busiest) hikes in the area. It's steep with an amazing view of Southern Berkshire County.
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Monument Mountain Reservation
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One of the most famous (and busiest) hikes in the area. It's steep with an amazing view of Southern Berkshire County.
Up and down hike in Stockbridge, MA. 30-45 minutes to the top. At the top, there is a tower you can climb for an awesome view.
Lauras Tower
Up and down hike in Stockbridge, MA. 30-45 minutes to the top. At the top, there is a tower you can climb for an awesome view.
Tennis, pickleball, fitness. Call ahead to reserve!
Bousquet Sport
100 Dan Fox Drive
Tennis, pickleball, fitness. Call ahead to reserve!
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Norman Rockwell Museum
9 Glendale Road
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Beautiful trails with a famous view.
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Olivia's Overlook
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Beautiful trails with a famous view.
Beautiful hike to large falls.
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Bash Bish Falls
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Beautiful hike to large falls.
Closest attraction to the house. Wonderful gardens to walk around. They offer many activities on the weekends.
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Berkshire Botanical Garden
5 East Stockbridge Lee Road
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Closest attraction to the house. Wonderful gardens to walk around. They offer many activities on the weekends.
Fun for everyone. Baby animals, antique houses, and a great little cafe with food from the farm.
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Hancock Shaker Village
1843 West Housatonic Street
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Fun for everyone. Baby animals, antique houses, and a great little cafe with food from the farm.
A local winery with live music and a tasting room.
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Balderdash Cellars
502 East St
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A local winery with live music and a tasting room.
A great fall activity! Apple picking, pumpkins, apple cider donuts, and more!
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Windy Hill Farm
686 Stockbridge Road
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A great fall activity! Apple picking, pumpkins, apple cider donuts, and more!
Fantastic lake for swimming, kayaking, canoeing. Motorboats are also allowed. To access the beach, you must be a Stockbridge resident. Simply tell the attendant the address of where you are staying (11 Quiet Knoll) and they will let you in.
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Stockbridge Bowl
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Fantastic lake for swimming, kayaking, canoeing. Motorboats are also allowed. To access the beach, you must be a Stockbridge resident. Simply tell the attendant the address of where you are staying (11 Quiet Knoll) and they will let you in.
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Clark Art Institute
225 South Street
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One of the largest collections of modern and contemporary art. This place is not to be missed. Fun for all ages.
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MASS MoCA
1040 Mass MoCA Way
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One of the largest collections of modern and contemporary art. This place is not to be missed. Fun for all ages.
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Berkshire Museum
39 South Street
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Fabolous for sightseeing. In the summer they have live music. In the fall and winter, they offer fun family activities, including a pumpkin show and a holiday lights show.
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Naumkeag
5 Prospect Hill Road
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Fabolous for sightseeing. In the summer they have live music. In the fall and winter, they offer fun family activities, including a pumpkin show and a holiday lights show.
Local dairy farm. There is a store that offers local dairy products, including ice cream.
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High Lawn Farm
535 Summer Street
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Local dairy farm. There is a store that offers local dairy products, including ice cream.
Outdoor music venue. Home of the Boston Symphony Orchestra. One of the most famous sites in the Berkshires. Not to be missed. Pick a show, bring a picnic (including chairs and a blanket), and enjoy a night for the entire family.
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Tanglewood
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Outdoor music venue. Home of the Boston Symphony Orchestra. One of the most famous sites in the Berkshires. Not to be missed. Pick a show, bring a picnic (including chairs and a blanket), and enjoy a night for the entire family.
Local brewery.
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Big Elm Brewing
65 Silver Street
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Local brewery.
The highest peak in Massachusetts. Take a drive to the top for breathtaking views. For serious hikers only - it takes 6 hours to get to the top.
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Mount Greylock
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The highest peak in Massachusetts. Take a drive to the top for breathtaking views. For serious hikers only - it takes 6 hours to get to the top.