Emily's Guidebook to the Berkshires
Skiing, Snowboarding, and Snow Sports
Ski mountains you can drive to within 30 minutes.
Ski Butternut
380 State RdYou get discounted tickets on Wednesdays!
Smallest mountain in the area. Recently under new ownership with a lot of updates.
115 locals recommend
Bousquet Ski Area
101 Dan Fox DrSmallest mountain in the area. Recently under new ownership with a lot of updates.
Jiminy Peak
37 Corey RdThe largest mountain in the area.
Steepest slopes in the area. Close to two cozy restaurants - John Andrews and The Old Mill.
329 locals recommend
Catamount Mountain Ski Resort
78 Catamount RdSteepest 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.
Frankie's
80 Main StHomemade 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.
117 locals recommend
The Red Lion Inn
30 Main StOne 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.
53 locals recommend
Alta
34 Church StGreat 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.
20 locals recommend
Pizzeria Boema
84 Main StDelicious funky pizza. Same ownership as Frankies Italian Restaurant.
Baba Louie's Sourdough Pizza
42/44 Railroad StBest pizza in the county. Hands down.
Gourmet Japanese restaurant. If you like spicy, get the Afghani roll!
101 locals recommend
Bizen Gourmet Japanese Restaurant and Sushi Bar
17 Railroad StreetGourmet 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.
75 locals recommend
Old Mill
53 Main StCoziest 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!
54 locals recommend
District Kitchen & Bar
40 West StA hip restaurant. Large bar. First-class cocktails. Muscles are the favorite!
Michaels of Stockbridge
5 Elm StLocal friendly bar.
Comfort meals. Reservations needed, perhaps days ahead.
55 locals recommend
Cafe Adam, Bar and Restaurant
420 Stockbridge RdComfort meals. Reservations needed, perhaps days ahead.
Great breakfast sandwiches and coffee. Healthy options are abundant.
82 locals recommend
No. Six Depot Roastery & Cafe
6 Depot StGreat 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.
36 locals recommend
Great Barrington Bagel Company
777 S Main StNew 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.
Barrington Brewery & Restaurant
420 Stockbridge RoadLocal 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!
203 locals recommend
The Prairie Whale
178 Main StFun 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.
52 locals recommend
Xicohtencatl Restaurant
50 Stockbridge RdBest Mexican food in the area. Family-owned. Margaritas are top-notch.
Neighborhoods
Lenox
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.
188 locals recommend
Great Barrington
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.
69 locals recommend
Stockbridge
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.
14 locals recommend
Robin’s Candy
288 Main StA dream spot for all ages. Every candy you can possibly imagine, from all over the world. Dark chocolate salted caramels are to die for.
Rubiner's Cheesemongers
264 Main StEverything you need for the charcuterie of your dreams.
Nejaime's Wine Cellar
3 Elm StGreat selection of wine.
Most helpful staff in the area. They will answer any question and will even carry your order to your car.
15 locals recommend
Domaney's Liquors and Fine Wines
66 Main StMost 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!
64 locals recommend
Berkshire Mountain Bakery Inc
367 Park StWell-known bakery. Bread, pastries, pizzas, etc. Grab a jar of the Berkshire Honey Company honey with your bread order!
Chocolate Springs Cafe
55 Pittsfield RdGourmet chocolate. Enough said.
Soco Creamery
5 Railroad StThe best ice cream in the Berkshires. Hands down.
Spa & Relaxation
Canyon Ranch Lenox
165 Kemble StA well-known luxury spa, famous worldwideSp
Miraval Berkshires
55 Lee RdSpa 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.
112 locals recommend
Monument Mountain Reservation
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.
10 locals recommend
Laura Lookout 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.
Norman Rockwell Museum
9 Glendale RdOlivia's Overlook
Hiking TrailsBeautiful trails with a famous view.
Bash Bish Falls State Park
Falls RoadBeautiful hike to large falls.
Closest attraction to the house. Wonderful gardens to walk around. They offer many activities on the weekends.
118 locals recommend
Berkshire Botanical Garden
5 W Stockbridge RdClosest 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.
161 locals recommend
Hancock Shaker Village
1843 W Housatonic StFun for everyone. Baby animals, antique houses, and a great little cafe with food from the farm.
Balderdash Cellars
81 State RdA local winery with live music and a tasting room.
A great fall activity! Apple picking, pumpkins, apple cider donuts, and more!
20 locals recommend
Windy Hill Farm
686 Stockbridge RdA 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.
20 locals recommend
Stockbridge Bowl
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.
The Clark Art Institute
225 South StOne of the largest collections of modern and contemporary art. This place is not to be missed. Fun for all ages.
382 locals recommend
MASS MoCA
1040 Mass MoCA WayOne of the largest collections of modern and contemporary art. This place is not to be missed. Fun for all ages.
Berkshire Museum
39 South StFabolous 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.
109 locals recommend
Naumkeag
5 Prospect Hill RdFabolous 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.
32 locals recommend
High Lawn Farm
535 Summer StLocal 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.
58 locals recommend
Tanglewood
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.
Big Elm Brewing
65 Silver StLocal 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.
213 locals recommend
Mount Greylock
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.