Old Town Winchester

Aug.2022 I’ve been here several times over the years. I’ve just now decided to leave a review. Great day trip and enjoy the beautiful surroundings. Great shops, restaurants, and live entertainment.

such a beautiful little town just happen to stop by on our way home from vacation, I definitely recommend walking through.

Old town Winchester is an amazing destination. As a runner I absolutely love the pedestrian mall. Totally flat. Very wide. A great place to burn off calories from over eating fast food like McDonald’s. Lots of historic buildings. Very charming. I love the vibe here. Also neat antique shops and restaurants. Very cute downtown

Had a great time visiting all the shops and taking in the all the beautiful historic buildings. 3 hours passed in no time and we went to put more money in the meter at 6pm to stay for dinner. Didn't need to bc there's no fee for parking after 6! We left after 9... we spent 6 hours there & would have stayed longer if we didn't have to get up early in the morning. We ate at Ellies. The food, drinks, dessert, coffee & service were great! FYI most stores don't have public restrooms, but there are public restrooms that cost .25 to use. There's a 10 minute period you can use the restroom for & then the door automatically opens on its own!! It's like an elevator door & you can't stop it from opening LOL, so make sure you can do your business in that amount of time or it could be embarrassing!! There is a warning that let's you know, but it could be bad if you're having issues!

Super enjoyable location for a stroll, and lots of eating options. Surrounding street parking is free on Saturdays and Sundays. There is a small water feature that kids can get wet in, and a nice mix of shade, sun and seating areas throughout.

Nice little shopping area in Winchester, we visited on a Saturday around 1PM. Street parking in the area is free on weekends, coin or pay by app at other times. A lot of history in the area and many restaurants to choose from. A lot of the store fronts were permanently closed or closed for the weekend. Splash pad was here for the little ones but very busy since it was sunny and hot. Really no shade of visiting during this time of day so it can get hot walking this strip.

Really a great place to visit, beautiful colonial buildings, charming in every way. Perfect for a walking tour of the historic sites. I didn't do any shopping but it looks like there are high-end stores for everybody.