Best Restaurants for Special Occasions in Winchester

We like eating out on the patio, especially with the live music.

Great wine list. Good food choices from the menu and specials of the day. Upscale and comfortable dining facility. Server, Jack and table service by others, always attentive and happy to serve. We will return. We have dined at all of the Napoli restaurants. They are on the top of our list.

I have been wanting to go back to Annie gunn’s for years and we finally made it and it was well worth the wait! Every meal was exceptional, our service was the best I’ve had in a long time, and the wait times for each course were perfect (we did app, entrees and dessert). I cannot wait to go back!

Tara was the absolute best! Love it when servers give personal opinions as well as feedback from prior tables. Really makes the final choices on what to order so much better! It’s not an inexpensive option, but it’s definitely worth the price! We over ordered on food because the college kid at home would handle what was left. Ordered shrimp cocktail, crab stuffed mushrooms, a filet, a strip steak, crab cake, shrimp, hash browns and creamed spinach. Everything was perfect! 10/10 for sure on every item! Bar items were blood orange grapefruit margaritas and an espresso martini that were both on the cocktail list and were excellent! Ordered a B52 coffee that was not on the drink menu, but was perfectly made. Also had Woodford and a glass of Justin cab that Tara recommended. Bar team makes perfect drinks! Looking forward to next time. Complemented the hostess on the way out and told her how much we enjoyed the service. She took the time to add Tara’s name to our profile so we can have the same server when available. That’s a great touch, plus we really appreciated the optional complimentary valet parking on such a cold evening! So glad we had cash on hand so we were able to take advantage of the extra service and thank them for being there with a gratuity!

We had an amazing experience. The waiter (Alexis) was so nice, she made it such a pleasant evening. She asked if we were dinning for a special occasion and we explained it was a farewell dinner as our sister in law was visiting from Spain and going back this week-end. To our surprise, when the chocolate fondue came, she brought my sister in law a gift of chocolate covered strawberries with a plate with a good luck message. It was such a special gesture, not expected. All the servers were amazing as well. This is now a annual tradition we have every year as winter break and family visits come to an end.