Our Berkshire Favorites
Food scene
113 Main St, Sheffield, 5 min ride from the house!
Great pizza selections or make your own. Our favorites are Hannah Bella and Pollo Loco. They also sell ice cream from our favorite farm, High Lawn (see below for more info on High Lawn).
6 locals recommend
Roberto's Pizza
113 Main Street113 Main St, Sheffield, 5 min ride from the house!
Great pizza selections or make your own. Our favorites are Hannah Bella and Pollo Loco. They also sell ice cream from our favorite farm, High Lawn (see below for more info on High Lawn).
42 Railroad St, Great Barrington, 7 min drive. Excellent sourdough pizza spot. It is best to put in your order earlier as they get swamped between 7-8 pm.
121 locals recommend
Baba Louie's Sourdough Pizza
42/44 Railroad St42 Railroad St, Great Barrington, 7 min drive. Excellent sourdough pizza spot. It is best to put in your order earlier as they get swamped between 7-8 pm.
18 Elm Ct, Sheffield, 5 min ride. Delicious sandwiches, wraps, salads. There are a few locations, of which one is in Sheffield, and the other one is in Great Barrington. A favorite is the Oooh, Mexico sandwich.
20 locals recommend
The Marketplace Kitchen and Cafe
18 Elm Ct18 Elm Ct, Sheffield, 5 min ride. Delicious sandwiches, wraps, salads. There are a few locations, of which one is in Sheffield, and the other one is in Great Barrington. A favorite is the Oooh, Mexico sandwich.
47 Railroad St, Great Barrington, 5 min ride. Delicious brunch spot using fresh and local farm products. We highly recommend this one!
12 locals recommend
Marjoram + Roux
47 Railroad Street47 Railroad St, Great Barrington, 5 min ride. Delicious brunch spot using fresh and local farm products. We highly recommend this one!
282 Main St, Great Barrington, 5 min ride. Great better-than-a diner-type of the restaurant with a variety of tasty food options. Luca loves their Mickey Mouse-shaped pancakes, as a 5-year-old
would!
32 locals recommend
GB Eats
282 Main St282 Main St, Great Barrington, 5 min ride. Great better-than-a diner-type of the restaurant with a variety of tasty food options. Luca loves their Mickey Mouse-shaped pancakes, as a 5-year-old
would!
30 Main St, Stockbridge, MA 01262, 20 min ride. The Inn is one of the most quintessential Berkshire hotels in the area. Great for dinner or brunch in their outdoor garden.
117 locals recommend
The Red Lion Inn
30 Main St30 Main St, Stockbridge, MA 01262, 20 min ride. The Inn is one of the most quintessential Berkshire hotels in the area. Great for dinner or brunch in their outdoor garden.
389 Stockbridge Rd Great Barrington, 12 min ride. Our favorite Mexican place. Fantastic food and great outdoor seating.
10 locals recommend
Agaves Mexican Grill
389 Stockbridge Rd389 Stockbridge Rd Great Barrington, 12 min ride. Our favorite Mexican place. Fantastic food and great outdoor seating.
50 Stockbridge Rd, Great Barrington, 12 min ride. Another fantastic authentic Mexican spot. Delicious margaritas and lovely outdoor seating area.
52 locals recommend
Xicohtencatl Restaurant
50 Stockbridge Rd50 Stockbridge Rd, Great Barrington, 12 min ride. Another fantastic authentic Mexican spot. Delicious margaritas and lovely outdoor seating area.
420 Stockbridge Rd Ste 3, Great Barrington, 12 min ride. Fantastic food, beautiful interiors, and great outdoor seating available.
55 locals recommend
Cafe Adam, Bar and Restaurant
420 Stockbridge Rd420 Stockbridge Rd Ste 3, Great Barrington, 12 min ride. Fantastic food, beautiful interiors, and great outdoor seating available.
178 Main St, Great Barrington, 7 min ride. Pricey but great food. Plan and make a reservation. Great outdoor seating.
203 locals recommend
The Prairie Whale
178 Main St178 Main St, Great Barrington, 7 min ride. Pricey but great food. Plan and make a reservation. Great outdoor seating.
224 Hillsdale Road, South Egremont, 11 min drive. Selected as
one of the World’s 25 Best Farmstead Restaurant Experiences by The Daily Meal. Beautiful outdoor seating is available.
99 locals recommend
John Andrews
224 Hillsdale Rd224 Hillsdale Road, South Egremont, 11 min drive. Selected as
one of the World’s 25 Best Farmstead Restaurant Experiences by The Daily Meal. Beautiful outdoor seating is available.
420 Stockbridge Rd, Great Barrington, 11 min ride. Nice outside seating, great handcrafted beer selection, and a variety of food options.
51 locals recommend
Barrington Brewery & Restaurant
420 Stockbridge Road420 Stockbridge Rd, Great Barrington, 11 min ride. Nice outside seating, great handcrafted beer selection, and a variety of food options.
17 Main Street South Egremont, 7 min ride. Our go-to spot in the summer with outdoor seating and live music.
50 locals recommend
The Barn
17 Main St17 Main Street South Egremont, 7 min ride. Our go-to spot in the summer with outdoor seating and live music.
5 Railroad St, Great Barrington, 5 min ride. A must-stop for delicious locally made ice cream.
45 locals recommend
Soco Creamery
5 Railroad St5 Railroad St, Great Barrington, 5 min ride. A must-stop for delicious locally made ice cream.
198, Main St. Great Barrington, 7 min ride. Great bread and pastries! The bakery is located in the new Flying Church building next to the Prairie Whale restaurant.
Pixie Boulangerie
198 Main Street198, Main St. Great Barrington, 7 min ride. Great bread and pastries! The bakery is located in the new Flying Church building next to the Prairie Whale restaurant.
65 Silver St., Sheffield, 7 min ride. It is a solar-powered brewery that makes 6 of its staples year-round plus taproom only releases. All of their beers are crafted to reduce gluten.
31 locals recommend
Big Elm Brewing
65 Silver St65 Silver St., Sheffield, 7 min ride. It is a solar-powered brewery that makes 6 of its staples year-round plus taproom only releases. All of their beers are crafted to reduce gluten.
356 S. Main St, Sheffield, 6 min ride. Not only do they produce a wide array of award-winning spirits, but they also have a very diverse garden program. Their greenhouses and gardens focus on growing cocktail/spirit-centric herbs and botanicals. Drop by for a visit, pick up some of their seasonal herbs, get some expert cocktail advice, or taste through their line of spirits.
35 locals recommend
Berkshire Mountain Distillers
356 S Main St356 S. Main St, Sheffield, 6 min ride. Not only do they produce a wide array of award-winning spirits, but they also have a very diverse garden program. Their greenhouses and gardens focus on growing cocktail/spirit-centric herbs and botanicals. Drop by for a visit, pick up some of their seasonal herbs, get some expert cocktail advice, or taste through their line of spirits.
264 Main St, Great Barrington, 6 min ride. Our absolute favorite
cheese shop sells the best bread around, specialty pasta, wine, and chocolate. This shop embodies everything that our family is.
52 locals recommend
Rubiner's Cheesemongers
264 Main St264 Main St, Great Barrington, 6 min ride. Our absolute favorite
cheese shop sells the best bread around, specialty pasta, wine, and chocolate. This shop embodies everything that our family is.
125 Main St, Sheffield. Winter market at Dewey Hall 10 am – 1 pm on the second Saturdays of December 11, January 8, February 12, and March 12.
Sheffield Farmers' Market
125 S Main St125 Main St, Sheffield. Winter market at Dewey Hall 10 am – 1 pm on the second Saturdays of December 11, January 8, February 12, and March 12.
18 Church St, Great Barrington. Every Saturday, 9-1 pm through
November 13. They often have live music and yummy local fresh food stands.
35 locals recommend
Great Barrington Town Hall
Church Street18 Church St, Great Barrington. Every Saturday, 9-1 pm through
November 13. They often have live music and yummy local fresh food stands.
Activities
Route 23, South Egremont, 10 min ride from the house.
329 locals recommend
Catamount Mountain Ski Resort
78 Catamount RdRoute 23, South Egremont, 10 min ride from the house.
Ski Butternut
380 State Rd380 State Rd, Great Barrington, 15 min ride from the house.
78 Tyringham Rd, Monterey, MA, 25 min ride. Our favorite local lake with a public beach; parking passes are not needed. Lifeguards are on duty during the summer season. The beach is small but sandy and perfect for kids.
7 locals recommend
Lake Garfield Beach
78 Tyringham Rd78 Tyringham Rd, Monterey, MA, 25 min ride. Our favorite local lake with a public beach; parking passes are not needed. Lifeguards are on duty during the summer season. The beach is small but sandy and perfect for kids.
Benedict Pond Road, Benedict Pond Rd, Great Barrington, 30 min ride. This is a shallow artificial pond that connects to the Housatonic River. Previously a swamp, trees were cleared in the
1930s and built a dam. The water is clean and calm, perfect for swimming or paddleboarding. The area also has designated picnic areas with grills.
20 locals recommend
Benedict Pond Loop
Benedict Pond Road, Benedict Pond Rd, Great Barrington, 30 min ride. This is a shallow artificial pond that connects to the Housatonic River. Previously a swamp, trees were cleared in the
1930s and built a dam. The water is clean and calm, perfect for swimming or paddleboarding. The area also has designated picnic areas with grills.
508 Canaan Road / Route 295, Richmond, Massachusetts 01254, 35 min ride. They were voted one of the top 5 places for pick-your-own apples in MA! Their secluded location offers
beautiful views of the Berkshire hills. Wine tastings are also available as Hilltop is home to the Furnace Brook Winery. They make delicious cider and the most delectable freshly made hot cider donuts.
41 locals recommend
Hilltop Orchards Home of Furnace Brook Winery
508 Canaan Rd508 Canaan Road / Route 295, Richmond, Massachusetts 01254, 35 min ride. They were voted one of the top 5 places for pick-your-own apples in MA! Their secluded location offers
beautiful views of the Berkshire hills. Wine tastings are also available as Hilltop is home to the Furnace Brook Winery. They make delicious cider and the most delectable freshly made hot cider donuts.
Hikes
1.7-mile loop trail around the Benedict pond, 30 min ride. Hikers along this trail can enjoy water views almost the entire length around. It I beautiful all year round, and we do it with our five-year-old.
Benedict Pond Road
Benedict Pond Road1.7-mile loop trail around the Benedict pond, 30 min ride. Hikers along this trail can enjoy water views almost the entire length around. It I beautiful all year round, and we do it with our five-year-old.
Monument Mountain Reservation, a 3.8-mile-long trail of a moderate hike. We did it with our son, and with some complaining, he did it! It was also snowing and very cold in his
defense, so it was a bit harder to summit it.
53 locals recommend
Monument Mountain
Monument Mountain Reservation, a 3.8-mile-long trail of a moderate hike. We did it with our son, and with some complaining, he did it! It was also snowing and very cold in his
defense, so it was a bit harder to summit it.
4G85+29, Mt. Washington, MA 01258, 25 min ride. Beautiful moderate 2.1-mile hiking trail. This is the highest waterfall in Massachusetts and a popular scenic destination. The dramatic final pitch of Bash Bish Brook drops about 80 feet into an emerald plunge pool. Enjoy a hike to experience the wonder and beauty of this deep, verdant gorge. Nearby, Taconic State Park in New York offers more visitor amenities, picnicking, swimming, and camping.
282 locals recommend
Bash Bish Falls State Park
Falls Road4G85+29, Mt. Washington, MA 01258, 25 min ride. Beautiful moderate 2.1-mile hiking trail. This is the highest waterfall in Massachusetts and a popular scenic destination. The dramatic final pitch of Bash Bish Brook drops about 80 feet into an emerald plunge pool. Enjoy a hike to experience the wonder and beauty of this deep, verdant gorge. Nearby, Taconic State Park in New York offers more visitor amenities, picnicking, swimming, and camping.
716-732 S Undermountain Rd, Sheffield, MA 01257, 11 min ride. A
moderate 1.3-mile out-and-back trek that leads to a ~80-foot tall waterfall. Hikers will find parking directly off Route 41 in a small pull-off at the coordinates provided.
22 locals recommend
Race Brook Falls
716-732 S Undermountain Rd, Sheffield, MA 01257, 11 min ride. A
moderate 1.3-mile out-and-back trek that leads to a ~80-foot tall waterfall. Hikers will find parking directly off Route 41 in a small pull-off at the coordinates provided.
The trail is right in front of our house across the Kellogg Rd. You will see hikers passing by the house frequently. You may notice the signs for the trail all around the area as it meanders through the Berkshire towns.
37 locals recommend
Appalachian Mountains
The trail is right in front of our house across the Kellogg Rd. You will see hikers passing by the house frequently. You may notice the signs for the trail all around the area as it meanders through the Berkshire towns.
Relax and Enjoy
297 West St., Lenox, Massachusetts 01240, 3o min ride. Tanglewood is the summer home of the Boston Symphony Orchestra and the Boston Pops. From spring through fall, Tanglewood hosts a large variety of live music performances.
58 locals recommend
Tanglewood
297 West St., Lenox, Massachusetts 01240, 3o min ride. Tanglewood is the summer home of the Boston Symphony Orchestra and the Boston Pops. From spring through fall, Tanglewood hosts a large variety of live music performances.
-55 Lee Road, Lenox, Massachusetts, United States, 01240, 25 min
ride. Perched atop 380 protected acres in the Berkshires, the digital device-free resort is home to several restaurants, a Life in Balance Spa, and multiple pools—making this bucolic hillside setting ideal for unwinding and relaxing. A must-visit!
16 locals recommend
Miraval Berkshires
55 Lee Rd-55 Lee Road, Lenox, Massachusetts, United States, 01240, 25 min
ride. Perched atop 380 protected acres in the Berkshires, the digital device-free resort is home to several restaurants, a Life in Balance Spa, and multiple pools—making this bucolic hillside setting ideal for unwinding and relaxing. A must-visit!
Farms
119 Park St N, Great Barrington. Open seven days a week, 8 am-6 pm. Buy farm-fresh produce or eat already made food by their chef on the farm using their grown foods.
27 locals recommend
Taft Farms
119 Park St119 Park St N, Great Barrington. Open seven days a week, 8 am-6 pm. Buy farm-fresh produce or eat already made food by their chef on the farm using their grown foods.
535 Summer St, Lee, 20 min ride. A must-visit for both kids and grown-ups. The farm is huge with baby cows to pet, gorgeous views, and delicious food. Get a scoop (or two if you have a huge
appetite) of their delicious ice cream or fresh ghee, milk, eggs, cheese, and a bunch of other delicious foods at their farm shop. We go there every weekend in summer.
32 locals recommend
High Lawn Farm
535 Summer St535 Summer St, Lee, 20 min ride. A must-visit for both kids and grown-ups. The farm is huge with baby cows to pet, gorgeous views, and delicious food. Get a scoop (or two if you have a huge
appetite) of their delicious ice cream or fresh ghee, milk, eggs, cheese, and a bunch of other delicious foods at their farm shop. We go there every weekend in summer.
686 Stockbridge Rd, Great Barrington, 20 min ride. Great for berry or apple picking. It is also a design and garden shop: beautiful flowers and gorgeous views from their berry farm.
20 locals recommend
Windy Hill Farm
686 Stockbridge Rd686 Stockbridge Rd, Great Barrington, 20 min ride. Great for berry or apple picking. It is also a design and garden shop: beautiful flowers and gorgeous views from their berry farm.