Restaurants near Chesterwood

149 restaurants available nearby

1. The Red Lion Inn

4.4

Price: Expensive

• Contemporary American • Stockbridge

Booked 28 times today

Since welcoming its first guests in 1773, The Red Lion Inn has earned a reputation for outstanding food and genuine country hospitality. Those traditions are continued today by Executive Chef Jon Sterrett, whose kitchen features contemporary cuisine that is rooted in the region's history and harvests. Emphasizing the use of fresh, local ingredients and a huge proponent of buying locally and sustaining the region, Chef Sterrett regularly updates the Inn's menus to reflect the bounty of each season. Guests choose from the elegant Main Dining Room and the cozy Widow Bingham's Tavern. The wine list offers 500 plus selections, and has received the Wine Spectator best of Award of Excellence for ten consecutive years; Sommelier Tim Eustis helps pair wines with meals. If you would like to dine in the Tavern, please choose Bar when making your reservation.

A photo of Gateways Dine & Drink restaurant

2. Gateways Dine & Drink

4.3

Awesome(403)

Price: Moderate

• Farm-to-table • Lenox

Welcome to Gateways Dine & Drink, located in the historic Gateways Inn!Our menu has something for everyone to enjoy. Fresh dishes created by our chef and amazing staff for our locals and visiting guests alike. Our tasty grass-fed beef burger and salmon dishes are guest favorites! But don't forget to leave room for dessert...Please inquire about private events, up to and including wedding receptions.

A photo of The Old Inn On The Green restaurant

3. The Old Inn On The Green

4.8

Exceptional(970)

Price: Very Expensive

• Contemporary American • New Marlborough

Booked 3 times today

Dining at The Old Inn on the Green is an extraordinary experience: fine wine, great food, attentive, knowledgeable service and the dining rooms illuminated only by candle light. Chef and Owner Peter Platt, along with his team, work to create innovative and memorable meals that are an event unto themselves. Currently, we are offering a $85 prix fixe menu with 5-6 choices per course every night we are open. The hours for dinner are Wednesday through Sunday 5:30 pm to 9:00 pm for both indoors and in an all new screened outdoor room. The wine list is graced with an array of thoughtfully selected estate bottled wines from France, California, Italy and around the world. In addition to candlelight, in the colder months there are wood burning fireplaces in each room. A copy of our current menu can be found on the home page of our website www.oldinn.com.

A photo of Wm. Farmer and Sons restaurant

4. Wm. Farmer and Sons

4.5

Awesome(1228)

Price: Expensive

• American • Hudson

Booked 15 times today

Our barroom and restaurant is currently open Friday through Tuesday for dinner and features craft cocktails, light bites and a wide range of seasonal culinary offerings inspired by the bounties of local Hudson Valley farms. Not just farmers in name, we believe in supporting farmers and producers who share in our passion of growing and preparing the finest products imaginable. *You will be allowed to cancel your reservation at any time but please keep in mind that no shows and reservations canceled within 3 hours of your reservation time will be charged $25 per person. Due to the high number of restaurant reservation cancellations and no shows, our cancellation policy is not flexible, and the fee cannot be waived.*Pavilion seating is fully covered and sat rain or shine- In the event of inclement weather we cannot guarantee alternative indoor seating

5. Pillow Cafe

3.9

Excellent(206)

Price: Very Expensive

• American • Becket

The Pillow Cafe is the perfect dining option before or after a show at Jacob's Pillow! Dine al-fresco under our tent on the beautiful and historic grounds, which rest on the ancestral homelands of the Muh-he-con-ne-ok or Mohican people. Reservations start in May and are strongly encouraged.Executive Chef Stephen Will uses the finest, locally sourced ingredients to cultivate a delicious menu of appetizers, entrees and desserts. Enjoy the audience-favorite chilled lobster roll, or the cooked-to-order filet mignon, or a hearty Charcuterie spread! Take delight in choosing a libation, be it wine, beer, cocktails or mocktails! A 2023 OpenTable Diners Choice Award Winning Restaurant, we hope you will join us for a memorable dining experience which features the finest from The Berkshires.

6. Josie's Table

4.8

Exceptional(1033)

Price: Moderate

• American • Albany

Booked 37 times today

Josie's Table offers amazing local farm to table cuisine accompanied by our signature craft cocktails.Something new and unique to the Albany area.

7. La Bella Valatie

5.0

Exceptional(117)

Price: Expensive

• Italian • Hudson

Booked 6 times today

La Bella Restaurant & Pizzeria in Valatie, NY is an Italian restaurant where the true taste of the old country reigns supreme. The old family recipes used at La Bella remain true to the mouthwatering homemade dishes prepared in Mama's Cucina Italiana. In Italy, using only the finest and freshest ingredients in the preparation of the meal, is of the utmost importance. At La Bella we believe that is one tradition to revere and to follow every day.We hope you will join us soon for lunch, dinner, a pizza, or a slice to go.Buon Appetito!

A photo of The Barn Kitchen & Bar at The Williams Inn restaurant

8. The Barn Kitchen & Bar at The Williams Inn

4.7

Exceptional(616)

Price: Expensive

• American • Williamstown

Booked 15 times today

Join us at The Barn, the signature restaurant of The Williams Inn. The Barn serves familiar New England classics, seasonally inspired, locally sourced, masterfully prepared cuisine – prepared with an open mind and a fresh vision. Our restaurant has been thoughtfully designed especially for those who crave dining experiences that inspire a deeper connection with the community.

A photo of American Bounty at The Culinary Institute of America restaurant

9. American Bounty at The Culinary Institute of America

4.7

Exceptional(4186)

Price: Expensive

• American • Hyde Park

Booked 6 times today

With a focus on the seasons and products of the Hudson Valley, contemporary and traditional regional dishes are brought to life in an honest and flavorful way by CIA students under the instruction of world-class faculty at the American Bounty Restaurant. Rounded out with a top-tier American wine list and comfortable warm service, this casually elegant restaurant sets the stage for an unparalleled dining experience in New York’s Hudson Valley.

A photo of Max Downtown - Hartford restaurant

10. Max Downtown - Hartford

4.8

Exceptional(170)

Price: Very Expensive

• American • Hartford

Booked 46 times today

Located right in downtown Hartford since 1996, Max Downtown continues to add to all that the city has to offer with its legendary service, food and drink selection. Max Downtown has won a number of awards including Connecticut Magazine's Best for Overall Excellence, Hartford Magazine's Best Power Lunch Spot, Best for Business Entertaining and Best Wine List; has been featured in the Hartford Courant's Great Steaks: The State's Sizzling Best and was rated "Don't Miss" by the New York Times.With a significant list of vintage and non-vintage wines stored in-house, Max Downtown is excited to additionally offer its stunning wine mezzanine as a focal point. Our selection is bound to have the perfect accompaniment for your occasion whether it’s by the glass or by the bottle.If spirits are more your style, Max Downtown's whiskey bar features a broad selection of international bourbons, ryes, scotches and whiskeys crafted across the globe, from Kentucky to Japan.

See what locals rave about

From verified diners like you

T
Tracy
Greater Boston •1 review
5.0
Dined 2 days ago
The Red Lion Inn is iconic. Quintessential New England and always a joy to visit. Our lunch today did not disappoint. All tasty and well presented. The portions are modest for the price but leaves room for dessert. Apple pie, warmed Camabert and chocolate mousse were not only beautiful to look at it but mouth watering delicious. The Service was excellent! A must go to, if you’ve never been. And if you have, go back!
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The Red Lion InnPrice: Expensive• Contemporary American• Stockbridge
•
4.4
P
PamVIP
Greater Boston •23 reviews
5.0
Dined 6 days ago
What an incredible experience! The food, drinks, atmosphere, and service were all wonderful. Donna, our server for the evening, was incredible. Although this is a destination restaurant for us, we will be sure to add this into our annual rotation!
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The Old Inn On The GreenPrice: Very Expensive• Contemporary American• New Marlborough
•
4.8
E
Ellen
New York City •24 reviews
5.0
Dined 7 days ago
I always enjoy this restaurant. It is constantly a great place to dine whether it is just 2 or a large party.
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Wm. Farmer and SonsPrice: Expensive• American• Hudson
•
4.5
D
Darren
New York City •31 reviews
5.0
Dined on Nov 1, 2024
The service and food were great. The live piano music was amazing as well. The only thing was that there was a large gathering in the bar area that was really loud and disruptive to the diners in the restaurant area. Otherwise, it was a great time.
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Gateways Dine & DrinkPrice: Moderate• Farm-to-table• Lenox
•
4.3
D
Daniel
New York City •6 reviews
5.0
Dined on Aug 22, 2024
Fantastic amenity for patrons! Made for. Great evening.
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Pillow CafePrice: Very Expensive• American• Becket
•
3.9

Restaurants near Chesterwood

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149 restaurants available nearby

1. The Red Lion Inn

2. Gateways Dine & Drink

3. The Old Inn On The Green

4. Wm. Farmer and Sons

5. Pillow Cafe

6. Josie's Table

7. La Bella Valatie

8. The Barn Kitchen & Bar at The Williams Inn

9. American Bounty at The Culinary Institute of America

10. Max Downtown - Hartford

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