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Winchester, VA Things to do, eat and see

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Nestled in the Shenandoah Valley, Winchester has made a name for itself in history through the Civil War, several historical figures residing in it (including a young George Washington), and the infamous Apple Blossom festival. Located roughly an hou...
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Entertainment

Fun entertainment venues and activities in Winchester

 
Rebecca Mehalic profile picture
Alamo Drafthouse is a chain of movie theaters started in Texas, and Winchester was its first Winchester location. Alamo is known for providing food and a wide variety of alcoholic and non-alcholic drinks, having a strict no talking policy, and hostin...

The Winchester Alamo hosts several clubs and special events throughout the year--including but not limited to Psycho Cinema (for horror fans), a Film Club, and movie festivals.
Alamo Drafthouse Cinema Winchester
 
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Located on the Downtown Mall, Back to the Media is a video game and record store with an arcade in the back. They have a healthy assortment of machines ranging from pinball to arcades games like galaga. All games are set to free to play and you can p...
Back to the Media Arcade
 
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The Shenandoah Valley Discovery Museum is located on the downtown mall and offers a range of activities for kids of all ages. I've taken friends kids here before and they always have a blast!
Shenandoah Valley Discovery Museum
 
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The Family Drive-in located in neighboring Stephen City is one of the few remaning (a little over 300 left) drive-in theaters in the United States. It's well-run and there are two screens of movies to choose from, a playground for kids and a snack ba...

It is highly recommended you get here at least an hour before the movie starts in order to get settled and avoid the heavy traffic that ensues.
The Family Drive-in Theatre
 
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One of the quirkest things around Winchester, Dinosaur Land has been around since the 70s and features dozens of giant dinosaurs. They actually add one additional dinosaur a year (though some older dinosaurs are looking like a t-rex took a bite out o...

Though this is targeted to kids I can safely recommend it for adults who love dinosaurs (as an adult who has visited it and had almost as much fun as her friends 4-year old daughter).
Dinosaur Land
 
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Located on the downtown mall, Bright Box has an assortment of different entertainment featured on a regular basis. Everything from comedy shows to plays, dueling pianos and musical acts.
Bright Box Theater

Historical Sites and Museums

As a hot spot during the Civil War (it changed hands between the Union and Confederate armies over 70 times!) and prominent town in Virginia's early history, Winchester is host to several historical sites. It's the perfect place to visit for any hist...

 
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I can't say enough great things about this amazing museum! Not only is the museum itself massive and well curated, it features a massive, well-maintained garden. This is a wonderful place to spend an afternoon or relaxing morning. They also often hav...
Museum of the Shenandoah Valley
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Abram's Delight is a beautifully, well-preserved home that's over 200 years old and serves as a museum. The property is quite beautiful as well!
Abram’s Delight
 
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There once was a young man named George Washington who was a surveyor and later became the first president of the United States. This building (which was acutally moved from its original location) served as George Washington's office when he worked a...
George Washington's Office
 
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The home of the infamous country singer who hailed from Winchester.
Patsy Cline Historic House
 
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A large historical site that offers a ton of historical markers and trails. This is a great place to spend an afternoon walking around and exploring.
Third Winchester Battlefield Park
 
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A museum located on the downtown mall that focuses on the Civil War. The first floor is free but the upper floors will cost money.
Shenandoah Valley Civil War Museum

Outdoor Adventures

The Shenandoah Valley is a beautiful place and Winchester offers several fantastic places to take it all in

 
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A beautiful park and great place to talk a leisurely walk through or a relaxing picnic.
Jim Barnett Park
 
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Located a few miles outside of Winchester in Boyce, Blandy Experimental Farm will be one of the best arboretums you ever visit. Run by the University of Virginia and serving in part as a research site, Blandy is Massive and has offers for everyone. F...

I venture it at various times throughout the year to catch new things in bloom. Even in the dead of winter there's something to see.
Blandy Experimental Farm
 
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Abram's Creek is great for bird-watching and if you want a place to enjoy a walk. It is short and can be finished in around 30 minutes.
Abrams Creek Wetlands Preserve
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Located a couple miles outside of Winchester, Sky Meadows is a beautiful park worth venturing to. It hosts a variety of trails and a peaceful setting to take in the natural beauty of the Shenandoah Valley.
Sky Meadows State Park
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Food, Coffee and Dessert

Great places to eat a meal, grab a coffee or dessert while you're visiting Winchester

 
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Mr. Noodle and Rice has been around for over twenty years and offers an assortment of Asian dishes ranging from sushi to bento boxes and bulgogi. 

This is a must-stop stop for my husband and I whenever we're in the area and for good reason. Their sushi is especially good (especially the lasagna roll--do yourself a favor and get it).
Mr Noodle & Rice
 
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Sabai Thai is a great Thai resturant located on the Winchester downtown mall. They offer a wide variety of dishes ranging from pad thai, drunken noodles and curry. There are plenty of pescatarian and vegetarian options as well.

I highly recommend their red curry!
Sabai Thai Winchester
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Papermill is a local favorite for breakfast. They offer standard breakfast fare ranging from omelettes to pancakes, breakfast sandwiches to southern breakfast favorites. Their pancakes are quite good!
Papermill Place
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Taqueria Guadalajara is a great Mexican restaurant offering a variety of menu options.
Taqueria Guadalajara
 
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Tropical Island Coffee & Cafe is a cozy Jamaican restaurant located on the downtown mall. They are well-known for their chicken (I recommend getting their jerk chicken).
Tropical Island Coffee & Cafe
 
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Hideaway Cafe is a cozy coffee shop located in downtown Winchester. It has a good amount of seating and offers an assortment of teas, matcha, coffee, food and pastries.
Hideaway Café
 
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Awabi is a great Japanese restaurant located on the down town mall. They have really good sushi and a cozy atmosphere.
Awabi Sushi Bar
 
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Moo Thru is a chain of ice cream shops in Virginia and one of their newer locations is in Winchester. They have a variety of flavors and options to customize.
MOO THRU
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Farmers Markets and Shops

There are several great farmer's markets in Winchester and surrounding towns. There's also quite a variety of shops and shopping centers to scratch that shopping itch

 
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Blue Plate is a wonderful local bookstore that has been around for almost twenty years. They predominately sell used books and offer a wide variety of options ranging from history to fiction, science fiction and young adult. 

Blue Plate may be my favorite used bookstore. Not only do they have a carefully curated collection (all their books are in good condition) but they clean all their used books before putting them on the shelf. I also love that they have a lot of old s...
Blue Plate Books
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A fantastic farmer's market that lets you pick you own produce, offers rides for the kiddos and has a nice shop to purchase locally grown and made goods!
Marker Miller Orchards
 
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Nibblins is a must visit for anyone who enjoys baking or cooking. Located on the downtown mall, Nibblins is a huge 2-story building offering everything you could imagine needing in your kitchen and several things you didn't even know existed! 

They also have a large clearance room on the second floor. Warning, the stairs are quite steep and hard for anyone with knee issues.
Nibblins
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Bell's is a mens clothing store that has been around for almost 100 years. Stepping inside is a nostalgia trip to a by-gone era.
Bell's Fine Clothing
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Back to the Media gets two mentions in this list--one for the great arcade it hosts in the back of the shop, the other for being a good video game and record store. If you're a gamer, its fun to explore the shelves and see if they have that game you'...
Back to the Media - Video Games Records & Comics
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A great shoe shop known for its customer service and selection that has been open for almost 100 years. It's located in the downtown mall and worth a stop if you're looking for a new pair of shoes.
Wilkins ShoeCenter
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Festivals and Seasonal Activities

 
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Taking place in May, the Apple Blossom festival hosts a wide variety of events and takes place over several days.
Shenandoah Apple Blossom Festival
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Horror fans rejoice--there's a haunted house in Winchester! Opening in September and running through Halloween, Haunted Nightmare offers a fun horror experience.
Haunted Nightmares
 
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The annual county fair that offers exhibits, rides, performances and delicious fair food.
Frederick County Fair
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Sight-seeing and other Tourist spots

Locations worth checking out and general tourist spots 

 
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The Hanley Regional Library is a beautiful building and worth venturing into just to see.
Handley Regional Library
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Also known as the downtown mall, you may have seen this place mentioned in quite a few places on the list. Several local businesses, restaurants and shops line its streets and its easy to spend an afternoon exploring its many offerings.
Old Town Winchester
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