Best restaurants near me in Chester, Vermont

Price

$$
$$$
$$$$

Cuisine

American

Italian

Steakhouse

Seafood

French

Pizzeria

Top Rated

Charming

Dog-friendly

Good for business meals

Good for groups

Good for special occasions

Great for craft beer

Dining Options

All dining options

Delivery only

Takeaway only

Seating Options

Bar

Counter

Standard

High Top

Outdoor

Accessibility

Wheelchair access

57 restaurants available nearby

How are Featured results ranked

1. The Fullerton Inn

4.2

Awesome(154)

$$$$

• American • Chester

Booked 1 time today

The Fullerton Restaurant features a modern twist on classic American dishes and flavor combinations, resulting in unique tastes and presentations that are innovative and delicious. The restaurant serves both lunch and dinner - guests can choose to dine in our more formal dining room, outside on the porch or in our cozy, old world tavern, complete with traditional oak bar and wood burning fireplace. A carefully crafted wine list complements the menu with a range of distinctive international selections.

2. Esmeralda

5.0

Exceptional(7)

$$$$

• Peruvian • Chester

Esmeralda is an experimental restaurant from Maria Rondeau and JuanMa Calderón of Boston’s beloved Celeste, La Royal, and opening in Boston this Spring - Rosa y Marigold! Located atop a Vermont hillside surrounded by nature, Esmeralda is Rondeau and Calderón’s country residence where guests come together for shared culinary experiences that merge local and Latin American flavors, sounds and culture.Each month during the Summer and Fall, Esmeralda hosts a weeklong series of events with menus featuring rustic takes on Peruvian classics as well as an all-day feast centered around the pachamanca, the ancient method of cooking in the ground. Dinners are served outdoors on the lawn and patio, as weather permits, or inside the dining room. Guests are encouraged to mingle over pisco sours while jazz plays from the speakers, and take in the stars around the fire pit after the meal. An evening at Esmeralda is an experience beyond the meal itself — it’s a dinner party every night.

3. The Grafton Inn

4.8

Exceptional(378)

$$$$

• American • Grafton

Booked 16 times today

The Grafton Inn is a proud supporter of Vermont’s pioneering farm-to-table philosophy. Our historic inn and two restaurants in southern Vermont offer on-site dining year-round and feature locally-sourced ingredients prepared by food-loving professionals to create timeless, hearty dishes that will please any palate.The Phelps Barn, originally a carriage house for guests' horses, provides a unique and rustic VT dining experience. Even the hayloft has been repurposed and renovated, providing an elevated seating area as well as our 8-tap bar. It is a fast pace restaurant with live music usually scheduled on the weekends.If you are looking for a quieter space to have dinner or celebrate a special occasion, we would recommend our 1801 Tavern located inside the Main Inn. This historic space provides a cozy and elevated dining atmosphere. Within the 1801 Tavern you’ll find our recently renovated Pine Room Bar with a working fireplace.

A photo of Black Rock Steakhouse restaurant

4. Black Rock Steakhouse

4.4

Awesome(684)

$$$$

• Steakhouse • Springfield

Booked 16 times today

Coming Soon!

5. Calcuttas

3.8

Excellent(39)

$$$$

• American • Ludlow

Booked 5 times today

Escape to Calcuttas, a culinary oasis in Ludlow, Vermont, located at the Fox Run Golf Club. This upscale casual restaurant offers a unique dining experience that combines fresh local ingredients with global flavors.Enjoy a warm atmosphere where delicious aromas blend with lively conversation. The spacious dining room features a cozy fireplace and large windows, showcasing stunning views of the golf course and Okemo Mountain.Complete your meal with a selection of tempting desserts. Experience the best of Vermont dining at Calcuttas, where every dish is crafted to delight your senses.

A photo of Red Slate at the Upper Pass Lodge restaurant

6. Red Slate at the Upper Pass Lodge

4.5

Awesome(98)

$$$$

• Contemporary American • Londonderry

Booked 1 time today

Casual Dining in a Family Friendly AtmosphereProudly Serving only Vermont Made Spirits , Beers and Wine

7. River & Rye

4.9

Exceptional(36)

$$$$

• American • Stratton

Booked 2 times today

River & Rye is a restaurant, bar, and inn located in the village of Jamaica, Vermont. We’re inspired by our community, our food system, and our desire to support a thriving rural economy. Our food and drinks are simple and delicious and integrate local products wherever possible. The vision for River & Rye comes from a local family with deep roots in Jamaica and a respect for what the community and its surrounding nature have to offer. They crafted River & Rye with the intention of sharing what they love about this place with friends new and old.

A photo of JJ Hapgood General Store & Eatery restaurant

8. JJ Hapgood General Store & Eatery

4.7

Exceptional(65)

$$$$

• American • Peru

Booked 7 times today

JJ Hapgood (aka HAPGOODS): 305 Main Street, Peru (802. 824-4800). HAPGOODS has been a neighborhood stalwart since 1827. Serving up Breakfast, Lunch, Dinner & Fun, Wednesday through Sunday. Join us for a stellar meal or stop in and peruse our curated selection of artisan giftables, vinyl records, craft food and drinks - or - bring home a little magic with one-of-a-kind finds.

A photo of Copper Grouse - Taconic Hotel restaurant

9. Copper Grouse - Taconic Hotel

4.4

Awesome(1688)

$$$$

• American • Manchester

Booked 48 times today

The Copper Grouse serves regionally-inspired, soulful dishes from the kitchen in a newly designed space. Not to be missed, our beverage program of classic cocktails, artisanal spirits, Vermont craft beers and a wide selection of Wines from regions spanning the globe. Reservations are recommended for all dining and all meal periods. Last dinner seating on Fridays and Saturdays is 9:00pm.

A photo of Table 43.1 at Black Bear Lodge restaurant

10. Table 43.1 at Black Bear Lodge

3.6

Very Good(118)

$$$$

• American • Stratton

Table 43.1 offers a comfortable, family-friendly, inviting dining experience in the main den of Black Bear Lodge. Dinner is open to the general public during posted hours. Swing by for some Italian fare accompanied by Vermont craft beers, wine, and seasonal drink specials. The children’s menu is always available in this family-friendly restaurant. Menu is subject to change.

Dining near Chester, Vermont at a glance

Updated on 06/10/2026

Esmeralda

View restaurant

Discover local gems

Exceptional reviews

American

Average bill amount

$40 and under

See what locals rave about

From verified diners like you

K
Kara
New York City •1 review
5.0
Dined 3 days ago
Amazing meal & very friendly staff Cant wait to go back next time we are up there
More info
Black Rock Steakhouse$$$$• Steakhouse• Springfield
•
4.4
D
Devon
Upstate New York •1 review
5.0
Dined 3 days ago
Best outdoor seating in Ludlow…looks out over the 18th hole at Fox Run surrounded by a beautiful, well kept, sunny garden area. Atmosphere can be lively on a busy golf day and always upbeat. Live music on some weekend days is always a nice surprise.
More info
Calcuttas$$$$• American• Ludlow
•
3.8
C
Cynthia
Vermont •2 reviews
5.0
Dined 5 days ago
As always the food was consistently good and the service was efficient, attentive and informative. I will always recommend the Grafton Inn
More info
The Grafton Inn$$$$• American• Grafton
•
4.8
G
Gerald
Virginia •10 reviews
5.0
Dined on 22 Aug 2026
The Fullerton Inn deserves a special trip to enjoy the food and ambience.
More info
The Fullerton Inn$$$$• American• Chester
•
4.2
OT
OpenTable Diner
Greater Boston •1 review
5.0
Dined on 24 July 2026
Amazing experience I would highly recommend. Dining outside with mountain views, incredible food, delightful people who bring an inviting spirit to the evening. Its much more than just a good dinner. An experience.
More info
Esmeralda$$$$• Peruvian• Chester
•
5

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Here are the most popular cuisines: American, Contemporary American, Brewery, Contemporary French / American, Steakhouse and many more.

There are 53 restaurants on OpenTable in Vermont.

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Best restaurants near me in Chester, Vermont

Price

Cuisine

Top Rated

Dining Options

Seating Options

Accessibility

57 restaurants available nearby

1. The Fullerton Inn

2. Esmeralda

3. The Grafton Inn

4. Black Rock Steakhouse

5. Calcuttas

6. Red Slate at the Upper Pass Lodge

7. River & Rye

8. JJ Hapgood General Store & Eatery

9. Copper Grouse - Taconic Hotel

10. Table 43.1 at Black Bear Lodge

Dining near Chester, Vermont at a glance

Esmeralda

American

See what locals rave about

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