Places to Visit in Winchester, Virginia

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Living in a small town has really been tough for me because grew up in New York. I lived the fast life and Winchester, Virginia slowed my pace down tremendously. The first two years here there were only two places I went to which was my university’s cafeteria and the student center.


(That one time the cafeteria had lobster before Thanksgiving Break)

Now don’t get me wrong I enjoyed it and there were times I was a bit bored, but I worked with what I had. In the cafeteria, I would run to the international food section and try to spice up my life. When it came down to the student center I made sure I was there for the fun events such as karaoke night, pool tournaments, ping-pong tournaments etc.

Luckily, I started making friends who lived off campus and had cars, which was absolutely amazing to me because I’m from the city and we don’t really need cars (WE ROAD TRAINS!). I was able to go to new places and really get to know this placed called Winchester. So I thought it would be great to give you the top places I would recommend visiting if you're stuck in Winchester, Virginia or bored and have nothing else to do.


                                                   (Proof that I road trains only)



My Top Four Favorite Places


1.     Tropical Island Coffee & Cafe
Address: 39 W Piccadilly St, Winchester, VA 22601
If you like Jamaican food this is the place to go! I personally love their beef patties with coco bread because it’s just absolutely amazing. The beef patty is already spicy, but when you add more Tabasco sauce it’s godly. I’ve also had the Jerk Chicken and rice and it was very taste add that with the festive bread it’s a wonderful lunch. If you’re Vegetarian as well Lloyd (that’s the name of the owner) will hook you up with a great amount of rice and steamed vegetables. This place is affordable and a great place to have a chill date so I highly recommend.
2.  Drive in movie theatre.
Address: 5890 Valley Pike, Stephens City, VA 22655
If you ever want to feel like you’re a part of the movie Grease this is the place to go. I can assure you that you will also get great instagram and snapchat photos here. I suggest you check the weather before you go because I went on a really hot night and my boyfriend and I were all dressed up sweating like crazy! There food is a bit pricey, so you could bring your own food, but there is a food charge for bringing outside food.
3. Hide Away Cafe
Address: 200 N Braddock St, Winchester, VA 22601
This isn't just any ordinary coffee spot. This is a coffee spot is a place to go away from all your problems and have a nice cup of coffee or hot chocolate (they also have a s'mores cinnamon bun that is my favorite!) It’s a wonderful community that has many events that are collaborating with so many different people. This is an LGBTQ* safe space and they even have cute hideaway rainbow stickers you could put on your laptop and support their business. Here are some events I’ve been to in this cafe: Disney Trivia, Drag Shows, Shenandoah University Dinner Dialogue, and Student Latino Initiative events.

4. Winchester Skating Rink
Address: 1629 Berryville Pike, Winchester, VA 22603
Have you ever wanted to be a character in the movie Roll Bounce? Well then this is the place to go! On Tuesdays (which is the only day I go) it’s $1 to get in and $1 to rent skates. They have a DJ that you can go to and request songs , as long as it is appropriate,  they have a concession stand to get food and a small arcade. It’s a perfect place to take your family or have a nice date. So if I were you I would definitely show up and be like “Skate rink goin’ up on Tuesday, it’s two dollas today on a Tuesday!”.

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