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Windward Grille Restaurant

109 Eastern Ave, Essex, MA 01929-1331
+1 978-768-0050
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  • Excellent62%
  • Very good29%
  • Average7%
  • Poor2%
  • Terrible0%
Travellers talk about
“steak” (16 reviews)
“haddock” (25 reviews)
Open Now
11:30 AM - 10:00 PM Hours
American, Seafood, Bar, Pub, Gluten Free Options
$$ - $$$
109 Eastern Ave, Essex, MA 01929-1331
All Details
Write a ReviewReviews (202)
Traveller rating
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Time of year

21 - 30 of 201 reviews

Reviewed 14 October 2017

When the ten of us want to get together we reserve a small room just for us. The service, quality, and choice of food is excellent.

Thank Donna G
Reviewed 13 October 2017

The stately Windward Grille is a fine experience! We were greeted by Tim as we entered and although busy had time for us , found us a table at the bar and insured a table when one was available. Kim the bartender was busy but...More

Thank Kevin I
Reviewed 3 October 2017

Had the pleasure to eat there twice while on vacation in MA. Lunch was a HUGE lobster roll that was delicious. Dinner, another day, was baked stuffed shrimp - again delicious. The service was excellent, our waitress was warm, friendly, professional at all times. Dining...More

Thank thephoenixagain
Reviewed 15 September 2017 via mobile

I had the steak - awesome. The service was excellent. I loved the great 'old England' style interior. Prices were good value for money. All in all a great time had.

Thank WalterLockhart
Reviewed 14 September 2017

I got my favorite food item here which is one of the specials, seafood marinara. It is fetticini with lots of shellfish and it is delicious. For an appetizer, I got the tomato basil soup which was great as well. Everything was great about this...More

Thank sleeper61
Reviewed 26 August 2017

This is old New England at its best. Essex is crowded with restaurants, especially seafood restaurants, so competition is tough. The Windward provides a more extensive and varied menu than the clam and lobster houses down the road. That doesn't mean their clam and lobster...More

Thank Z8364LHrichardt
Reviewed 18 August 2017

We ate there due to the good reviews. From outside looks very pretty, an old inn. One dining area was cute. The other 2 rooms were extremely plain and not really clean looking. The salad and soup were just eh... Iceberg lettuce salad.... thin no...More

4  Thank mittmott
Tim521, Owner at Windward Grille Restaurant, responded to this reviewResponded 25 August 2017

I don't understand what the age of the customers has to do with anything. Do you not like elderly people? What a shame, they are entitled to go out and eat also.

Reviewed 9 August 2017

Had the haddock which was fresh and delicious. Five of us had very good meals, great service, and prices were not too expensive.

Thank Mary A
Reviewed 8 August 2017

I went here with friends while we were visiting nearby Rockport and Gloucester, and we had a ball. Great wait staff, beautiful building and atmosphere, and a ghost story to boot. The food was truly wonderful. I had the mixed grill, which admittedly sounds odd...More

Thank Susan D
Reviewed 5 August 2017

Quaint, early American building, nice decor, excellent food, excellent service, very reasonable prices; Waiter even brought us a small cake for our anniversary. Worth the short ride from Gloucester for the pennywise who an outstanding meal.

Thank Don B
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Questions & Answers
18 December 2015|
AnswerShow all 4 answers
Response from Rgon11 | Reviewed this property |
I believe it is between 11 and 2 . However, calling them is recommended.
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Restaurant Details

Rating summary
  • Food
  • Value
Average prices
US$8 - US$24
Lunch, Dinner
Restaurant features
Takeout, Seating, Waitstaff, Parking Available, Free Off-Street Parking, Television, Wheelchair Accessible, Serves Alcohol, Full Bar, Accepts American Express, Accepts Mastercard, Accepts Visa, Accepts Discover, Reservations, Private Dining, Accepts Credit Cards
Good for
Groups, Kids, Business meetings, Special Occasion Dining, Local cuisine, Child-friendly
Open Hours
11:30 AM - 9:00 PM
11:30 AM - 9:00 PM
11:30 AM - 9:00 PM
11:30 AM - 9:00 PM
11:30 AM - 9:00 PM
11:30 AM - 10:00 PM
11:30 AM - 10:00 PM
Location and Contact Information
  • Address: 109 Eastern Ave, Essex, MA 01929-1331
  • Location: United States  >  Massachusetts (MA)  >  Cape Ann  >  Essex
  • Phone Number: +1 978-768-0050
Antique New England farmhouse with 1800's barn attached. Fireplaces lit during the winter months. Large rustic bar with high-top seating around bar area. Booth and table seating available in several dining rooms. Special value priced specials available Monday thru Thursday. Large parking area with easy wheelchair accessibility.
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