Chamaio’s guidebook
Best Restaurants in Pittsfield
Best Ramen in the Berkshires. The steamed Pork Belly buns are unreal. This place will instantly make you a repeat customer. Great beers on tap with fun friendly service.
20 locals recommend
Thistle & Mirth
44 West StBest Ramen in the Berkshires. The steamed Pork Belly buns are unreal. This place will instantly make you a repeat customer. Great beers on tap with fun friendly service.
Fancier upscale dining with great food and a fantastic cocktail bar. Great place for a date or even a solo glass of wine if you're in town by yourself.
54 locals recommend
District Kitchen & Bar
40 West StFancier upscale dining with great food and a fantastic cocktail bar. Great place for a date or even a solo glass of wine if you're in town by yourself.
Lovely wine bar and tapas restaurant. The food is delicious and allows you to have a little bit of everything. Enjoy live music on the weekends. Wine enthusiasts will enjoy the selection and general knowledge of the staff.
36 locals recommend
Mission
438 North StLovely wine bar and tapas restaurant. The food is delicious and allows you to have a little bit of everything. Enjoy live music on the weekends. Wine enthusiasts will enjoy the selection and general knowledge of the staff.
The best Italian in the Berkshires and likely one of the most popular restaurants as well. This is a very popular place located between Lenox and Pittsfield. This is a win every time and can accommodate larger groups. The food and wine selection are superb. Definitely call ahead of time to make a reservation.
34 locals recommend
Mazzeo's Ristorante
1015 South StThe best Italian in the Berkshires and likely one of the most popular restaurants as well. This is a very popular place located between Lenox and Pittsfield. This is a win every time and can accommodate larger groups. The food and wine selection are superb. Definitely call ahead of time to make a reservation.
Cool, eclectic vibe with amazing appetizers and great beer on tap. This woman owned local hangout has a fun vibe with lovely hosts and an art gallery in the back. Try the tacos... simply divine.
32 locals recommend
Methuselah
391 North StreetCool, eclectic vibe with amazing appetizers and great beer on tap. This woman owned local hangout has a fun vibe with lovely hosts and an art gallery in the back. Try the tacos... simply divine.
What's a town without its local Irish Pub! This is a winner. It's popular, has a huge tap selection, with your go-to Irish fare. Great place to catch a game if you're by yourself.
35 locals recommend
Patrick's Pub
26 Bank RowWhat's a town without its local Irish Pub! This is a winner. It's popular, has a huge tap selection, with your go-to Irish fare. Great place to catch a game if you're by yourself.
You want wings, beer, and the biggest burger you ever put your mouth on? This is the place. Massive Beer on Tap selection, very long bar that turns into a giant U shape at the end. Lots of seating available too. This is a local hang out, with the largest selection of mouth watering wings you may ever encounter. If you HAVE to watch TV while you eat, this is the place to do it. There entire perimeter of the bar is lined with Flat Screens.
Hangar Pub and Grill
1350 East StYou want wings, beer, and the biggest burger you ever put your mouth on? This is the place. Massive Beer on Tap selection, very long bar that turns into a giant U shape at the end. Lots of seating available too. This is a local hang out, with the largest selection of mouth watering wings you may ever encounter. If you HAVE to watch TV while you eat, this is the place to do it. There entire perimeter of the bar is lined with Flat Screens.
Sightseeing
Hiking, Mountain Biking, Camping. Drive up Look out at the top. This is one of my favorite places to bring the dog for a hike. It's also a fantastic place to go mountain biking. There's a great spot at the lower parking area to have a picnic with the family, or drive up the mountain and take in a wonderful view of the Berkshires.
44 locals recommend
Pittsfield State Forest
1041 Cascade StHiking, Mountain Biking, Camping. Drive up Look out at the top. This is one of my favorite places to bring the dog for a hike. It's also a fantastic place to go mountain biking. There's a great spot at the lower parking area to have a picnic with the family, or drive up the mountain and take in a wonderful view of the Berkshires.
Well established hiking and mountain biking trails with many different loops available. Wonderful lookout area at the top that gives you a view into New York State on a clear day. Great place to watch a sunset, but bring a flash light for the 1/2 mile trek back to the parking lot. Note: Park at the Arcadian Shop in Lenox. This is a very cool local outdoor store similar to REI with a great bike shop in the basement. Anyone in the store can give you great recommendations on hiking in Kennedy and any other great outdoor places to venture.
66 locals recommend
Kennedy Park
275 Main StWell established hiking and mountain biking trails with many different loops available. Wonderful lookout area at the top that gives you a view into New York State on a clear day. Great place to watch a sunset, but bring a flash light for the 1/2 mile trek back to the parking lot. Note: Park at the Arcadian Shop in Lenox. This is a very cool local outdoor store similar to REI with a great bike shop in the basement. Anyone in the store can give you great recommendations on hiking in Kennedy and any other great outdoor places to venture.
Beautiful stop on a windy road up the mountain past Tanglewood Music center. Get out and see a breathtaking view of Stockbridge Bowl (one of the larger lakes in the region) and beyond. There are also wonderful hiking trails off the parking lot that bring you to a higher lookout in a different direction. This view is incredible, but you have to work for it.
51 locals recommend
Olivia's Overlook
Hiking TrailsBeautiful stop on a windy road up the mountain past Tanglewood Music center. Get out and see a breathtaking view of Stockbridge Bowl (one of the larger lakes in the region) and beyond. There are also wonderful hiking trails off the parking lot that bring you to a higher lookout in a different direction. This view is incredible, but you have to work for it.
The highest mountain in the Berkshires, Mount Greylock offers one of the best drive up views you can find out here. The drive alone getting to the mountain itself is a beautiful trip to the northern end of the Berkshires. This will take half a day, but well worth it. If you're a road biker...and want a challenge. Try biking the paved road up to the lookout.
213 locals recommend
Mount Greylock
The highest mountain in the Berkshires, Mount Greylock offers one of the best drive up views you can find out here. The drive alone getting to the mountain itself is a beautiful trip to the northern end of the Berkshires. This will take half a day, but well worth it. If you're a road biker...and want a challenge. Try biking the paved road up to the lookout.
This is one of the larger tourist attractions in the area. An amazing state park located in the southern Berkshires, Bash Bish Falls is a relatively short uphill hike to a set of falls that is quite breathtaking. Pack a lunch and have a picnic. You'll be happy you did, because you won't want to leave once you're there.
282 locals recommend
Bash Bish Falls State Park
Falls RoadThis is one of the larger tourist attractions in the area. An amazing state park located in the southern Berkshires, Bash Bish Falls is a relatively short uphill hike to a set of falls that is quite breathtaking. Pack a lunch and have a picnic. You'll be happy you did, because you won't want to leave once you're there.
Grocery Stores
Like Whole Foods but older, better, and local. You will not be disappointed.
Guido's Fresh Marketplace
Like Whole Foods but older, better, and local. You will not be disappointed.
A commercial upscale grocery store. Everything is of better quality. It falls somewhere between your regular grocery store and Whole Foods. About a 15 minute drive from the house. If you like quality, it's worth the trip. There is also a Walmart, BJ's, and Home Depot, among other stores in the same vicinity.
19 locals recommend
Market32
555 Hubbard AveA commercial upscale grocery store. Everything is of better quality. It falls somewhere between your regular grocery store and Whole Foods. About a 15 minute drive from the house. If you like quality, it's worth the trip. There is also a Walmart, BJ's, and Home Depot, among other stores in the same vicinity.
Less than a mile from the house, this typical grocery store has all your essentials. Wine and Liquor store attached to the building.
80 locals recommend
Big Y World Class Market
200 West StLess than a mile from the house, this typical grocery store has all your essentials. Wine and Liquor store attached to the building.
Arts and Entertainment
This Premiere outdoor music venue is the home of the Boston Symphony Orchestra in the summer. It also attracts big name musical talent from all over the world. You can get a lawn or a shed ticket. But lawn tickets on a nice day is unbeatable. Bring a picnic and some wine.
Tanglewood
This Premiere outdoor music venue is the home of the Boston Symphony Orchestra in the summer. It also attracts big name musical talent from all over the world. You can get a lawn or a shed ticket. But lawn tickets on a nice day is unbeatable. Bring a picnic and some wine.
This museum is more than a museum. It's an experience. Look them up and find out what's happening while you're here. They also have live music events and other fun things going on for adults and children alike. A real gem.
382 locals recommend
MASS MoCA
1040 Mass MoCA WayThis museum is more than a museum. It's an experience. Look them up and find out what's happening while you're here. They also have live music events and other fun things going on for adults and children alike. A real gem.
If you like Shakespeare. This is where you need to be. If you like Theater. This is where you should see it. Shakespeare & Company has more than just Shakespeare on some of the most beautiful grounds in the area. Grab a cocktail at the bar and take a walk around. Then go enjoy a show, where you'll experience a magical night in the theater. If you've never seen a play... start here.
134 locals recommend
Shakespeare & Company
70 Kemble StIf you like Shakespeare. This is where you need to be. If you like Theater. This is where you should see it. Shakespeare & Company has more than just Shakespeare on some of the most beautiful grounds in the area. Grab a cocktail at the bar and take a walk around. Then go enjoy a show, where you'll experience a magical night in the theater. If you've never seen a play... start here.
A remarkable theater experience close to the house in Pittsfield. The Colonial puts on fantastic shows and draws the attention of well renowned actors all over the globe. If you see a show here, you will not be disappointed.
56 locals recommend
Colonial Theatre
111 South StA remarkable theater experience close to the house in Pittsfield. The Colonial puts on fantastic shows and draws the attention of well renowned actors all over the globe. If you see a show here, you will not be disappointed.
Another nationally recognized theater company that has been active in this space for a long time. The grounds keep getting updated and are more stellar every time I come here. Located in the historic town of Stockbridge you will get a theater experience that you won't forget. Wonderful performances year in and year out. This is a must visit.
61 locals recommend
Berkshire Theatre Group
6 East StAnother nationally recognized theater company that has been active in this space for a long time. The grounds keep getting updated and are more stellar every time I come here. Located in the historic town of Stockbridge you will get a theater experience that you won't forget. Wonderful performances year in and year out. This is a must visit.
The man, the myth, the legend. I mean... you have to go here! It's Norman Rockwell! It's actually a really eye opening experience. I learned so much more about Mr. Rockwell and the era that he depicts than I ever thought possible. A real eye opener. Love this place...I'm sure you will too.
344 locals recommend
Norman Rockwell Museum
9 Glendale RdThe man, the myth, the legend. I mean... you have to go here! It's Norman Rockwell! It's actually a really eye opening experience. I learned so much more about Mr. Rockwell and the era that he depicts than I ever thought possible. A real eye opener. Love this place...I'm sure you will too.
Breakfast joints
Lovely cafe with great breakfast options. Vegan and vegetarian friendly. Awesome coffee drinks.
51 locals recommend
Dotties Coffee Lounge
444 North StLovely cafe with great breakfast options. Vegan and vegetarian friendly. Awesome coffee drinks.
Great breakfast and lunch options. Cool vibes. Vegan and Vegetarian options. Food is fabulous.
17 locals recommend
The Marketplace Cafe
53 North StGreat breakfast and lunch options. Cool vibes. Vegan and Vegetarian options. Food is fabulous.
This is a cool, eclectic breakfast joint that is wonderful for brunch. Highly recommend, but can get very busy in the summer so get there early!
67 locals recommend
Haven
8 Franklin StThis is a cool, eclectic breakfast joint that is wonderful for brunch. Highly recommend, but can get very busy in the summer so get there early!