Ate here with friends when we were staying at the Country Inn at Highview B&B. The owners recommended it, and Trip Advisor reviews were good so we decided to try it - we weren't sorry.
The restaurant is located on one end of the Loudoun Street Pedestrian Mall and there are several parking lots and a parking garage nearby so it is a short walk. The Loudon Street Pedestrian Mall just completed renovation in the Spring of 2013 and it is a nice place to spend a few minutes browsing before or after eating - quite a few restaurants, some nice shops, etc.
We went on a Saturday night and were seated inside immediately - there are quite a few tables outside on the patio where you can people watch as you eat, as well as doors on one side of the restaurant that open up so it is almost like sitting outside even though you are in the building.
Our waitress was excellent - she got our drinks right away, took our appetizer and meal orders as soon as we were ready, made sure glasses stayed filled, etc. We had the spinach and artichoke dip with flatbread as an appetizer and it was very good - not nearly enough dip for all the flatbread you get but that is typical. In our group people had the cheesesteak, Brewbaker burger and pork medallions - all the food was served quickly and excellent. One in our group has had the real deal Philly Cheesesteaks in Philly and he said this one was the best one he'd eaten outside there. The burgers were large, cooked to order and very good. There were 3 large pork medallions in that order and they too were great.
This is a great location to spend a little time in the historic district and people watch, the atmosphere in the restaurant is nice (not fancy, just fun), the service was excellent and the food was very good. Definitely would recommend Brewbakers if you are looking for a place to eat in Winchester.