Restaurants near Chesterwood

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodFrenchMexican

Top Rated

CharmingFancyGood for business mealsGood for groupsGood for special occasionsGreat for brunch

Dining Options

All dining options

Delivery only

Takeout only

Seating Options

BarCounterStandardHigh TopOutdoor

Accessibility

Gender-neutral restroomWheelchair access

151 restaurants available nearby

How are Featured results ranked

1. The Red Lion Inn

4.6

Exceptional(3046)

$$$$Price: Expensive

• Contemporary American • Stockbridge

Booked 15 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 The Old Inn On The Green restaurant

2. The Old Inn On The Green

5.0

Exceptional(975)

$$$$Price: Very Expensive

• Contemporary American • New Marlborough

Booked 1 time 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 Gateways Dine & Drink restaurant

3. Gateways Dine & Drink

4.4

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.

4. Josie's Table

4.8

Exceptional(1110)

$$$$Price: Moderate

• American • Albany

Booked 46 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.

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

5. American Bounty at The Culinary Institute of America

4.8

Exceptional(4263)

$$$$Price: Expensive

• American • Hyde Park

Booked 64 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.

6. Pillow Cafe

3.9

Excellent(207)

$$$$Price: Very Expensive

• American • Becket

Booked 1 time today

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.

A photo of The Bocuse Restaurant at The Culinary Institute of America restaurant

7. The Bocuse Restaurant at The Culinary Institute of America

4.8

Exceptional(4471)

$$$$Price: Expensive

• French • Hyde Park

Booked 42 times today

Sleek and strikingly contemporary, The Bocuse Restaurant is named for the most famous chef in France, Paul Bocuse. Here, CIA students re-imagine the execution of classic French cuisine through the lens of ultra-modern cooking techniques under the instruction of world-class faculty. Enjoy casual yet sophisticated service alongside an exceptional French wine list and innovative cocktail program during your unique and exciting dining experience.

8. La Bella Valatie

4.9

Exceptional(124)

$$$$Price: Expensive

• Italian • Hudson

Booked 7 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!

9. Taiga Restaurant

4.3

Awesome(36)

$$$$Price: Moderate

• Russian • Hudson

Booked 1 time today

## Taiga Restaurant: A Culinary Journey Through the Wild Forest Nestled in the heart of Hudson, New York, Taiga Restaurant invites you to embark on a unique dining experience inspired by the untamed beauty of the ancient forest. Our menu celebrates the rich culinary heritage of indigenous peoples, offering a tantalizing fusion of ancient recipes and European culinary traditions. Step into our warm and inviting space, where modern elegance meets rustic charm. The ambiance is reminiscent of a cozy cabin nestled amidst towering trees, with flickering candlelight and the soft glow of natural wood. The aroma of wild herbs and spices fills the air, whetting your appetite for the culinary adventure that awaits. Our menu features a symphony of flavors, each dish crafted with the freshest seasonal ingredients. Start your journey with our signature appetizer, the Stuffed Peppers, bursting with savory beef, onion, and cheese, served with a vibrant tomato sauce. For your main course, indulge in the Salmon Burger with Siberian Herbs, a succulent Alaskan salmon patty topped with a medley of aromatic herbs and served on a toasted brioche bun. And for a sweet finale, don't miss our decadent Napoleon Cake, a layered masterpiece of flaky pastry, rich custard, and fresh berries. Taiga Restaurant is more than just a place to eat

10. The Stewart House

4.7

Exceptional(122)

$$$$Price: Moderate

• American • Catskill

Booked 3 times today

Please note reservations are for the 1883 Tavern Only. For large parties please call to reserve the private dining room. 518-444-83171883 Tavern features an Art Deco bar and dining room. Farm-sourced dishes comprise an ever-evolving menu. Enjoy dinner in a historical setting on the banks of the Hudson River with weekly specials, an inventive cocktail, fine wine or local craft beer. Happy first hour each day we’re open (half price drinks), live music on Thursday nights and a burger & beer special, Friday martini & mussels special (every martini comes with a side of mussels), Sunday Bloody Mary menu and special Sunday Roast dinner with all the fixings.

See what locals rave about

From verified diners like you

R
Robin
New York City •9 reviews
5.0
Dined 2 days ago
Our server Ty was great. The food was fantastic. The rest of the dining room staff were a little green and it showed.
More info
American Bounty at The Culinary Institute of AmericaPrice: Expensive• American• Hyde Park
•
4.8
R
Rose
Los Angeles •10 reviews
5.0
Dined 2 days ago
Another lovely lunch at Josie's. It was our friend's first visit and they were very pleased as we were.
More info
Josie's TablePrice: Moderate• American• Albany
•
4.8
R
RobertVIP
New York City •73 reviews
5.0
Dined 6 days ago
Another Home Run for The Old Inn. 9 out of 10 times you will be treated to an excellent dining experience.
More info
The Old Inn On The GreenPrice: Very Expensive• Contemporary American• New Marlborough
•
5
R
Richard
Greater Boston •1 review
5.0
Dined on Mar 13, 2025
Always a pleasure to dine at the Red Lion Inn, where I have been eating for 34 years. Excellent food and friendly service, and the atmosphere is warm and welcoming.
More info
The Red Lion InnPrice: Expensive• Contemporary American• Stockbridge
•
4.6
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.
More info
Gateways Dine & DrinkPrice: Moderate• Farm-to-table• Lenox
•
4.4

Explore OpenTable

Landmark
Neighborhood
City/Region

Prospect Heights Historic District
Northampton Downtown Historic District
Pittsfield Mall Shopping Center
Old Sturbridge Village
Turner Park
Dalton Avenue Plaza Shopping Center
Wachusett Mountain
One Stop Shopping Center
Catamount Ski Area
Big E
Worcester Common
Auburn Mall
Brimfield Antique Show
Springfield College
Breckwood Shopping Center
Galleria At Worcester Center Shopping Center
Park Square Historic District
Massachusetts Avenue Historic District
Big D Plaza Shopping Center
Springfield Museums

Stockbridge

Central and Western MA