Windward Tavern — Restaurant in Milton

Our friday night dinner group decided to go outside our comfort zone on New Years Eve and try the Windward Tavern. We arrived about 6 pm, and were seated promptly and had a nice table in the middle of the restaurant. The decor is rustic and everything is well placed to displace the sound from other tables. Usually you go to places now and they think you want to hear clinking and loud talking so that you cannot hear the person sitting next to you, This is not the case here, We could hear everything and the bar is located on the opposite side of the walls to deflect the hooting and hollering of the football game. For appetizers we ordered the Calamari and the blue cheese chips. The calamari was the best i have ever eaten, it was fried perfectly, and the inside was not chewy at all. very delish. The blue cheese chips was a pile of chips and had a great flavor! we really enjoyed them both. Service was excellent, our waitress (who had on a Detroit Red Wings shirt, sorry i am horrible with names...update, looked at receipt her name was Diana) Took awesome care of us. Gave us great recommendations and gave us a lot of time to look over the menu. We never once felt rushed like, we need to turn this table over 4 times tonight to make a profit. We all ordered something different, my prime rib was excellent, and i substituted green beans for the asparagus, some of the best green beans i have ever eaten. My wife ordered the salmon which had a great texture and taste it. Everything was delish!!! we really enjoyed this place and cant wait to go back. Its a true gem of a place and should be packed nightly. I want to go back to try their burgers that looked really phenomenal. Try this place, you wont at all disappointed and the prices were really reasonable for the amount of food and taste you received. Were there for 2 hours and enjoyed every second of it, happy new year to you all.... we will see you soon, and pass the word to our friend...

I have been a customer for years and always enjoyed great food, service and a nice patio. Today, however, I ordered a Turkey Club sandwich and what was served was a very basic turkey sandwich. For anyone reading and not familiar with what a club sandwich is, it is very specifically a triple decker sandwich invented 121 years ago at a World’s Fair and served the same universally at virtually every restaurant that offers this well known and established food item (see attached Google description)… everywhere other than the Windward Tavern who has opted to serve a basic turkey sandwich! When I asked the waitress, she had the look of a deer in the headlights, poor thing! When I asked the manager on duty, he proceeded to have an attitude and said, ‘well, that’s how we make it’! There was no offer to rectify the situation or even order a different item. I’ve had the same item at this same company’s Crabapple Tavern and they remarkably prepare it correctly as a triple decker sandwich. While the sandwich tasted good, I was very disappointed by both the way it was served and the attitude of the manager. I doubt I’ll go back and will opt for the Crabapple or Milton locations...

I rarely write negative reviews and I'm saddened to write it about this place because my family and I use to love the food here over the last 2 years.. but our last visit was very disappointing. First of all, we were seated at the patio and I guess the hostess never told anyone we were there so we sat there for 25+ minutes before we were acknowledged at all. We ordered chips and queso as an appetizer and it was almost inedible. The chips were stale and hard, the queso was thick and oddly tasted like tap water?? Not good at all. Our fries were cold and soggy with our entrees.. my burger was cooked well but it had zero seasons on it whatsoever. Same with my husbands fried shrimp, cooked well but absolutely no hint of flavor. This is really disappointing considering how expensive the food is here, a burger and fries being at least $20. Would have had a more tasty meal at a fast-food place, honestly. As i said, this has been a go to spot for my family and I for a long time, but not sure what has happened recently because the last few times have been hit or miss. Hate to say i probably won't be returning...