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Windward Grille Restaurant

Certificate of Excellence
$$ - $$$
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109 Eastern Ave, Essex, MA 01929-1331
11:30 am - 9:00 pm
Open now
All hours
Sun - Thu 11:30 am - 9:00 pm
Fri - Sat 11:30 am - 10:00 pm
More Info
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151 Reviews from our TripAdvisor Community

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Time of year
Showing 150: English reviews
Santa Rosa, California
Level Contributor
33 reviews
24 restaurant reviews
common_n_restaurant_reviews_1bd8 18 helpful votes
4 of 5 bubbles Reviewed 1 week ago

On a cool Fall evening, Windward Grille provided a lovely respite with excellent seafood in the cozy dining room. Essex is famed for its seafood (particularly clams) so you can't go wrong with selecting some. The food is well prepared and you will find many locals to share space with - - always a good sign.

Thank Barbara P
Reading, MA
Level Contributor
7 reviews
6 restaurant reviews
common_n_restaurant_reviews_1bd8 3 helpful votes
4 of 5 bubbles Reviewed 4 weeks ago

Came here after reading reviews on Trip Advisor for a Labor Day lunch with friends. We were seated right away and our server was excellent throughout. They had a decent list of craft beers and wine by the glass. In our group of four we ordered two types of haddock, one lobster roll and a chowder. All were very good... More 

Thank AuntLulu
Framingham, Massachusetts
Level Contributor
33 reviews
31 restaurant reviews
common_n_restaurant_reviews_1bd8 13 helpful votes
3 of 5 bubbles Reviewed 4 weeks ago

My Wife and I spent a day at Wingaersheek Beach; and decided to try the Windward Grill. It was highly rated in TripAdvisor and was on our way home. Our dining experience was disappointing; the Windward Grill, sadly, did not measure up to its reputation. Let me explain in detail: We both ordered the Mug of Clam Chowder. We both... More 

Thank Neil10468
Level Contributor
18 reviews
8 restaurant reviews
common_n_restaurant_reviews_1bd8 9 helpful votes
5 of 5 bubbles Reviewed September 14, 2016

This place never lets me down. The staff are 100%, the food is very fresh and reasonably priced for the portion. I have been here 20+ times and my review is long overdue!

Thank biztravelerBoston
Level Contributor
36 reviews
30 restaurant reviews
common_n_restaurant_reviews_1bd8 6 helpful votes
5 of 5 bubbles Reviewed September 11, 2016 via mobile

Always great drinks, food and bartenders! It's a nice home feeling, I recommend this place to all. Go enjoy!

Thank Sharon G
Level Contributor
21 reviews
12 restaurant reviews
common_n_restaurant_reviews_1bd8 6 helpful votes
5 of 5 bubbles Reviewed September 6, 2016 via mobile

Sure, if you wanna do the touristy thing, go for woodman's or some of the other waterfront places. If you want high quality seafood in a nice atmosphere, go to Windward! The spicy shrimp and scallops were worth the try. The clam chowder did not disappoint. I ordered the lobster & scallop Cannelloni and my friend ordered the lobster casserole.... More 

Thank Jill E
Level Contributor
18 reviews
12 restaurant reviews
common_n_restaurant_reviews_1bd8 3 helpful votes
2 of 5 bubbles Reviewed September 5, 2016 via mobile

After reading the reviews on TripAdvisor we had very high expectations for this restaurant. I am afraid that it was far from what we anticipated. While we waited for our table we went to the bar. The Strawberry Daiquiri was terrible. For dinner my wife had the grilled chicken which looked and tasted like it was cooked on a George... More 

Thank Jeffrey B
Boston, MA
Level Contributor
25 reviews
13 restaurant reviews
common_n_restaurant_reviews_1bd8 10 helpful votes
5 of 5 bubbles Reviewed September 4, 2016 via mobile

Excellent food and beautiful old building, go here instead of the tourist traps down the road. You don't have a water view, though if that's what you want. But I recommend coming here! The clam chowder was yummy, the lobster casserole was excellent (this was a special, so they might not always have). The seafood canneloni was great and unique.... More 

Thank cgeorgeBoston_MA
Gloucester, Massachusetts
Level Contributor
23 reviews
22 restaurant reviews
common_n_restaurant_reviews_1bd8 2 helpful votes
5 of 5 bubbles Reviewed August 26, 2016

This restaurant is one of the best in Essex. It has excellent quality food well served. Can accommodate over 100 guests.

Thank ecloutier2016
Lowell, MA
Level Contributor
62 reviews
35 restaurant reviews
common_n_restaurant_reviews_1bd8 24 helpful votes
5 of 5 bubbles Reviewed August 18, 2016

This was my first visit here after an afternoon spent on Cranes Beach and I wasnt disappointed. Last year we went to Woodmans where it seems like everyone goes but the Windward Grille might just beat out Woodmans. I had baked stuffed clams for an appetizer and they were delicious. For the main course I had an lobster roll which... More 

Thank jjenfa

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Restaurant Details

Rating summary
  • Food
    4.5 of 5 bubbles
    4.5 of 5 bubbles
  • Value
    4.5 of 5 bubbles
    4 of 5 bubbles
Average prices
$8 - $24
American, Seafood
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
Good for
Business meetings, Special occasions, Local cuisine, Kids, Families with children, Large groups
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: 19787680050
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.

Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Windward Grille Restaurant and other visitors
1 question
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danvers, ma
10 months ago

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Questions? Get answers from Windward Grille Restaurant staff and past visitors.
Posting guidelines
Typical questions asked:
  • Do you have gluten-free options?
  • Is there a dress code?
  • Do you allow dogs on the outdoor patio?