This is still our favorite restaurant by far! Wonderful food with beautiful presentation. Great drinks that aren't watered down like every other restaurant. All the staff are very friendly.
TAPS (The Atlantic Paranormal Society) from the Ghost Hunters on the Sci-Fi channel did a ghost hunting investigation here and it will air Wednesday, Nov. 19th @ 9pm on the Sci-Fi Channel.
Channel 50 for those of you in Gloucester!!
The Windward Grille is hands down our favorite restaurant. The atmosphere is very warm & inviting. The clam chowder is the best we've had on the North Shore, and the Lobster bisque is excellent! The Roast Duck entree that Rosalina makes is OUT OF THIS WORLD!! Another favorite of mine is the Seared Sea Scallops in Lobster Cream Sauce with Asparagus - YUM! The owners, Tim & Vicki are always around to welcome the customers and they are very accepting to suggestions, not like other restaurants close by that shun upon anything new! Go see Jill & Tom at the bar - they're the best!!! We also love the brunch on Sundays!
My friends and I have had dinner several times in the past few weeks. We love the food offerins, the owners are friendly and the wait staff is very good.
The decor has recently been changed to include 18th century style paintings. This historic property is a wonderful, warm setting for a romantic dinner, hearty lunch or private event in the beamed ceiling function room upstairs.
I don't understand the recent reviews. My Wife and I frequent the Windward Grille pretty much weekly, sometimes more. I have to tell you that we have never had a bad meal. The waitstaff is wonderful and you can pretty much get whatever you want. We have witnessed that whenever there is a problem, management handles it with coutesy and professionalism. Let's face it, you can't always have things run smooth. We love coming in when there is entertainment. It's just a wonderful bar to hang out in. We love the fact that the owners are there all the time ready to greet us warmly. We love it at the Windward Grille!!!! src='/images/5star.gif'>
Posted by: Charlie Bowden at March 20, 2008 02:20 PMi've been there 3 or 4 times and had one marginally ok meal at best...
the last time it was really bad i thought...good ingredients murderouly overcooked, to sum it up. wish the food was half as comforting as the nice atmosphere...it's like they're talking the talk but can't walk the walk 
My husband and I returned to the Windward grilled a couple weeks ago and brought a friend with us. I don't know what happened, but either they were having an off night or the quality of the food has gone down hill. I ordered the warm spinach salad that I have ordered before and it arrived with hardly any bleu cheese, mushrooms, or even dressing on it - it was basically a plate of lettuce for $8. My husband's baked stuffed shrimp were tiny and flavorless and my prime rib was nothing to rave about. Not worth the price this time by any means. I hope things improve...
Posted by: Wendy at February 29, 2008 02:42 PMAware of the mixed reviews we had read, my boyfriend and I went to Windward Grille on a recent Tuesday, between lunch & dinner.
I was pleasantly surprised. The interior is warm and comfortable, and the food is very good. Being winter, we both chose comfort foods. His turkey dinner and my baked scallops were just fine. We started with lobster bisque and clam chowder, both of which were good.
I actually loved the warm, old house feeling of the place, and the bar was great. Based on our first experience there, we would not hesitate to go back again.
Posted by: Cannoli at January 10, 2008 10:13 PMHad dinner there last night(four people) two meals were great and two were not........the 10oz filet was only about 7oz and was dry and tough....the baked stuffed sole was poor and had frozen taste( a commercial fisherman ordered it!!) the drinks were good as was the service but overall the rating gets no stars....i have eaten at Dexters and was never dissatisfied.....the prices were a little high but if all the meals were good it would not have mattered.....this establishment need a lot of improvement
Posted by: Mike at December 21, 2007 09:06 PM 
Excellent food but somewhat spotty service. The waitress seemed preoccupied and getting her attention was not easy. Other than that the food and atmosphere were both excellent. Would go back again, without a question.
Great food, love the bar. Service has always been good. Usually order the seafood canelloni or lobster raviollis.
I'm a local, been here 4 times, each time was just so-so. The dining rooms off of the bar always feel like a no mans land, no atmosphere and dead silent on the week nights. There are so many more lively places on the North Shore....Sorry Windward, you leave me empty.
Posted by: glenn at August 15, 2007 04:22 PM
We go out to dinner most Saturday nights. The Windward Grill Restaurant is one of our favorites! Good food, good drinks, good service & good prices. Plus easy parking. Busy over the weekends altho' we have always been seated within a reasonable time. Like sitting in the bar. Try Tuesday - Thursday.
My boyfriend and I went there for dinner last night. Sat in the bar area at a corner table. Very cozy. Service was very good. Food was excellent. My boyfriend had the fishermans platter, which at first I thought was a bit expensive, but after seeing the plate, realized it was a good value. The fried haddock was THE BEST I have ever had. Piping hot, golden brown, moist. All the rest was excellent too. I only wish they had a New Zealand Sauvignon Blanc on the wine list!
Posted by: maureen at June 20, 2007 12:22 PMMy wife and I visited the Gloucester area as we do every year, and late last August we dined at the Windward and were not disappointed,we're surprised by some of the negative reviews posted on this site. We'll return this year as well and have recommended it to some friends who are visting the Cape Ann area for the first time.
We have been to this restaurant about 10 times in the last 8 months, and it is well worth the 40 mile drive to get there for us. I understand everyone has differant tastes, but trust me, tell them how you want your food and that is the way it will arrive. This area is known for great restaurants and this one is one of the best. One of the staff (Victoria, by name) has always treated us as family and that alone will keep us comming back. Regards Bob Thomas
We go there all the time and have always had great food & wonderful service. Their Sunday Brunch is wonderful and so are the Grand Mimosas! The owner is usually there to greet people and the bartenders are friendly and attentive. The newly renovated pub-side is cozy and charming and the flat-screen tv's are great for watching sports! Don't miss this gem...the food is on par if not better than Blue Marlin Grille but the service and atmosphere are so much nicer!
I have been going to the Windward for over a year, consistantly and have never had a disappointing experience. The food is always great, Tom, who tends the bar is excellent and so sweet and I don't find the prices high at all. It sounds like they need to revisit their preparations for red meat, however--all those people can't be wrong. I'd recommend the seared tuna salad or the tenderloin salad. Steak tips are good too. Give it a try.
Posted by: laura at February 28, 2007 02:20 PMAmbiance is excellent.
Service is excellent.
Food is mediocre and nto worth the price.
There is a reason that the Blue Marlin, down the street, is always packed and the Windward is not!!
Went to Windward Grill with my Valentine for a relaxing meal. We were greeted graciously as we entered and offered a seat in front of a fireplace. Waitress was pleasant and brought some very tasty warm bread over. Appetizers: Scallops wrapped in bacon were cooked perfectly and were juicy-sweet. The Cream of Broccoli soup was verrrrrry creamy and had good flavor although a bit thicker than I prefer. For entrees I had the grilled salmon with dijon sauce, which they did a nice job not smothering the fish with. The horseraddish mashed potatoes and sauteed spinach went well with the fish. I was happy with my dinner..... however, my girl had a less than desirable experience. She ordered the Small cut of Prime Rib with a combo of stuffed shrimp. The waitress "forgot" to order the shrimp but rushed it out in about 5 minutes. It was truly the worst prime rib I'd even seen or tasted. Just a sad looking slab of grissled meat that was not by any strecth of an imagination tender. The shrimp were smallish and only two were served. The squash she was served was indeed tasty, at least. My girl also had something floating around in her water, apparently from a dirty glass.
Overall a disappointment considering the prices they charge. Even though the atmosphere has some appeal, we sat close enough to a group of "loud talkers" that that was somewhat spoiled as well. Usually do not discount a place after one shot but in this case, my money will find a better experience. 
lousy
Posted by: elaine at February 9, 2007 05:45 PMI live right down the street and I love going there whenever I can. The atmosphere is great and the staff is super friendly! Great menu!!!
Thumbs up!
We ate at the Windward grill this past sat. 1/20/2007 how totally disappointing. I loved the Hearthside Restaurant and thought we would give the Windward a try.
We were there for lunch one person ordered a crock of clam chowder which was not even hot and was mostly potatoes. I ordered the house salad which had brown lettuce and shriveled tomatoes.
We both ordered the fish sandwiches and both were not hot at all. Instead of fries I asked for mashed potatoes which had to be sent back to the kitchen to be reheated along with the fish.
A very expensive lunch and very very disappointing.
I loved the Hearthside when you came in they would serve you bean dip with crackers and you felt so relaxed there. Prices were alot better than the Windward and you got a great meal for your dollar. I would not go back to the Windward things would have to improve drastically. I would not recommend this restaurant to anyone.
Also at the next table from us they were very disappointed in the meal they received and had to send there's back also.
I loved the old Hearthside and worried that the Windward Grille wouldn't live up to it's predecessor. I was pleasantly surprised to have excellent food and service. The waitstaff has always accommodated my special requests. It has become my special restaurant for a great night out. I highly recommend it. It is reasonably priced with friendly service and quality food.Everyone should try it.
Went to The Windward Grille last night for dinner for the first time. Absolutely AWESOME. Fried clams for my boyfriend, salmon for me, both EXCELLANT. Our waitress, Jane Haskell was excellant as well, timely and service with a smile.
All three fish dishes were very good. Steak tips were not. Quite pricey.
The Windward Grille is our favorite place on Cape Ann. The remodeling is beautiful... they have a very classy, elegant bar area and the post and beam ceiling, dark wood, and candles make it the perfect cozy spot to go for a night out.
I have never (okay, almost never) been disappointed in the food. The spinach salad with roquefort, prime rib, baked stuffed shrimp and sirloin steak were all excellent. I did order the chicken dish once and it was a skimpy portion, bland and definitely over-priced. But out of 10 trips there, that is the only negative we encountered.
Posted by: Wendy at August 3, 2006 11:32 AMMy wife and I ate at the Windward grille last Friday night with our two kids. After our meal we both agreed that we would not be coming back.The Heartside has always been a nice and quiet place for us to have dinner on special occasions (birhdays,anniversary,ect...),but between the food and the service it would be our last time dinning at the old heartside, now known as the Windward grille. My wife and I both ordered steak dinners. Her filet minon was ordered well done.They offered to butterfly it for her,but when they brought it out it was so well overcooked it was to the point where half of it was burnt.I ordered the 12 oz N.Y, sirloin and when I got my dish.I was really disappointed on how thin the steak was. I been cutting meat for over sixteens years and I know what a 12oz steak should look like even after it's cooked. I figured my cut was about 8 to 10 oz with very little grill marks on it.Our waitress Amanda couldn't realize that our water glasses needed to be filled without asking, which was getting old after the fist time. All in all our experience at the Windward grille was very disapointing and I would not hesitate to tell our friends not to waste there time or money and go elsewhere.By reaing previous posts on this website we're not the only ones to get a bad dinner.
Posted by: Jay at July 30, 2006 05:15 PM
We have thought about stopping in many times since in was the Hearthside. Tonight we did on the way home from shopping. Very happy with the service. The King size rib was done to my liking. We eat out a lot, as we're almost blue hair, and enjoy good food. I'm sure we'll return for the hospitality, and reasonably priced dinners, etc. Had I read some of the other reports first We may have missed out. Thanks, Jack
hit or miss normally very good but once in a while sub par for the price. Still normally worth the time though.
i went here last month with my husband and another couple. i was very disappointed with my meal. i ordered a prime rib med rare. when my meal arrived it was well done and tough as a shoe. my waitress agreed that is was not medium and took it back for another piece. the next piece was cooked medium, but was still tough. i don't know what cut of meat it was, but it was not prime rib. doubt that we will be going back.
Service was very slow. Waitr person not very pleasant. Meals were not up to first class standards. Price was high, The old Hearthside was far superior. Will not be returning.
Posted by: E L Kane at May 31, 2006 07:49 AM
Went for lunch today, it was excellent!!! On a rainy day, you can't beat the atmosphere inside. So cozy, great service and yummy food.
Posted by: Heather at May 11, 2006 02:13 PM
Heard a couple of good reviews on this place. Thought we'd give it a try. Wow am I sorry. Don't mind paying good money for a nice meal. Have dined at wonderful resuatants all over. Zabaglione in Ipswich, Aujourd'hui in Boston, Hotel DeParis in MoteCarlo.
Service at the Windward Grill was nothing to write home about and the food served was something that any restaurature should be absolutely ashamed of! We had Lobster that was completely dried out and stiff as a BOARD. The rest of the meal was not any better. Don't expect this restaurant to last to long unless the owners manage to give the customers a decent meal for the money they charge. Not really asking too much.
I did leave a good tip for the waitress, as it was not her fault.
Management howevrer needs to hear how pathetic the food was.
My Husbend and I went here for valentines day. The food was great! we enjoyed it very much. we have also been there for lunch and it to was wounderful. the atmosphere was also fantastic. This is our new favoret place
Go and see for your self
If you haven't been here, GO!!! What an incredible place.
We were greeted with a smile and escorted to the bar when we asked where it was. So many times, a greeter will just point you in the direction and then be on their way.
Decor and lighting were perfect. TV's everywhere so we could enjoy the Oscars. A friendly bartender who was right along with us ripping on all the big Hollywood stars. Food can't be beat.
I'm sure children are welcome, but Moms and Dads should do this on their own. You deserve it.
Posted by: Laurie at March 7, 2006 08:39 AMOpps, my posing below was supposed to be for Alchemy. Read further down for my Winward review.
Posted by: SAC at March 3, 2006 03:53 PM
I am also a big fan. Have taken so many people here and everyone always loves it. The only problem is that it is so popular you have to remember to make a reservation!
Posted by: SAC at March 3, 2006 03:51 PM
Well, I've always been told that old people like good food for a good value. I suppose if you've been around long enough, you learn a thing or two.
I first went here with my Grandmother and the food was excellent, I had a gigantic fish sandwich that was piping hot and nearly the size of my head for only six dollars. I could only eat half of the monstersandwich. The restaurant caters to a blue head sort of crowd and when my boyfriend and I went out to lunch (we are in our twenties) we felt rather out of place. Yet, our food was absolutely delicious and I highly reccomend Windward to anyone looking for a hearty meal... just be advised it's not exactly a hip-hoppin' trendy sort of spot.
Posted by: Michelle at March 1, 2006 09:24 PM
I thought this would be better based on all the positive reviews. The menu is sort of old school for me -- not many ways to eat healthy here. We never got bread even after I asked for it. The bar area looked nice. I might stop there for a cocktail but I won't do dinner again.
Posted by: SAC at February 27, 2006 11:11 AM
My husband and I, along with another couple chose the Windward Grille for a recent Saturday night dinner. Needless to say, we won't be going back any time soon. Although we went on a Saturday night, we figured that by going at 6:15 we would beat the crowds. But we didn't. The place was very busy, which is good for them, but bad for us. Our waitress was nice, but incompetent. We had to ask for the complimentary bread, and then 10 minutes later it was delivered. We were off to a bad start, but we didn't know how bad. (although the bread was warm and tasty.) Our problems mostly dealt with service. The salads were fine, and so was the french onion soup. The scallop appy was also very good according to my friend. The reviews on the crabcakes, not so good - loaded with potato filler. An order of the fried clam appetizer was overcooked and was also sitting out for 5 minutes before it arrived barely warm at our table. Another order of the fried clams which was requested for dinner never arrived. Finally we asked to cancel the order, because at this time everyone else was all done eating. The waitress never advised us that the order was running late, how could she? We barely saw her all night. We had to hunt down the host to tell him to cancel the order. Items were served to us at different times, so none of us were eating together - awful timing from the kitchen. We left (or ran) out of the place almost 2 1/2 hours later after a completely unsatisfying experience. And, we are not the only ones who experienced this. My parents dined there about a month after it opened up and they said their service was awful also. We watched as the two hosts were running around the place all night helping deliver food and responding to customer calls. Definite potential, but they need to figure out some operations issues first.
Wow! What a great place to eat. After being a steady on Friday nights at Tom Sheas during off-season period, we chose Windward Grille one Friday night instead. It was recommended to me by a colleague in Lexington MA. So, we gave it a try, and have been back three times in two weeks. Wonderful Menu. Very Personable and Friendly Wait Staff. Very Reasonably Priced. Exceptional Meals. The Calamari is large and crispy. The Beef is cooked exactly to your liking, the Sour Dough Bread is a nice change to standard rolls and butter, and all meals were served in reasonable amount of time and at the temperature they should be served. They don't sit around in the kitchen on shelves to be served 10 minutes later, that's for sure. Hot when it should be Hot, and Cold when it should be Cold. I love the menu, the semi private side dining rooms, the staff, and the meals. I'll be back for sure! and Highly Recommend Windward Grille to Locals and Tourists.
My wife and I eaten at the Winward Grill at least a dozen times since it's opening. The building is beautiful and the color is great. The bar has been changed around from when it was the Hearthside and is usually quite busy. The menu is quite extensive There is quite a lot to choose from, whether you are a seafood lover or just want a good steak cooked to order. We usually try one of the daily specials, and have never been disappointed. We haven't tried the raw bar yet but the calamari, stuffed clams and chowder(s) have been fantastic. Portions are huge, and the presentations add greatly to the dining experience. We have found wait staff was attentive but not overbearing. Give the Winward Grill a try, you won't be disappointed.
I just ate there last week with the rest of the Cambece family. We went for lunch, I got the fish and chips, my brothers got fried clams and my dad got steak, I don’t remember when the ladies got. The food was good; service was ok for lunch time. There were not very many people there, but once again it was lunch. Everyone seemed friendly and the prices were reasonable
Cambece
Posted by: J.A. Cambece at December 5, 2005 11:42 AM
I just ate there last week with the rest of the Cambece family. We went for lunch, I got the fish and chips, my brothers got fried clams and my dad got steak, I don’t remember when the ladies got. The food was good; service was ok for lunch time. There were not very many people there, but once again it was lunch. Everyone seemed friendly and the prices were reasonable
We thought the Windward was great too. The Halibut was delicious as was the sirloin. Waitstaff seemed a bit put out, running up and down the stairs, but service was courteous though it could've been a bit more friendly....least no one addressed as "you guys" or "kids" or said "are you still working on that" Pet peeve of mine.
My wife and I stopped at what used to be the Hearthside. Wow, what a surprise. The building is beautiful. Great color. The inside is also incredible. What a great bar!!! It was very busy. There is alot to pick from on the menu so it was very difficult to choose. I got the grilled halibut and my wife got the filet mignon. Our meals came beautifully presented. Great portions. The desserts were also equally beautiful. I had the 7 layer chocolate cake and my wife had the lemon mousse with rasberry sorbet. The waitstaff was attentive but not overbearing. We will be back to try other things on the menu.
I ate at the Windward on opening night. The food was excellent. The service reflected an opening night, disorganized and not very warm. But, the food will be what brings us back. It was worth a bit of a wait. I'm hoping they will work on the staff training.
Windward Grill is less than weeks old, bustling, customer firendly, remodeled in most areas leaving the rustic brick walls and fireplaces from another age. The menu is comprehensive emphasizing steaks and prime rib. Raw oysters were to die for,mini Caeser salad contained tasty anchovies per request, martini was chilled, my wife's glass of CA Clos Du Bois Chardonnay was fruity/creamy. Her salmon was excellent minus the horseradish mashed potatoes with asparagus substitute again per request. My steak tips were huge portioned and rare per order with popcorn shrimp that melted in your mouth. Steak Fries were hot and excellent. Chef brought courses to our table. Windward Grill has already raised the bar for Cape Ann Restaurants in my opinion and we dine out weekly! Walls need some more paitings and place needs another wait person or two but we're already planning to go back.
The windward is incredible. The team of chefs delivering the food is outstanding. The entire restaraunt is brand new inside, but still has the authentic older feel. I have been 2 times already and will most definetly be frequenting here.
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