Winchester Travel Guide

  • Court House and Feltner Building
    Court House and Feltner Building
    by Ewingjr98
  • Court House Civil War Museum
    Court House Civil War Museum
    by Ewingjr98
  • George Washington Hotel
    George Washington Hotel
    by Ewingjr98

Winchester Things to Do

  • Shenandoah Valley Campaign...

    A Whirlwind in the Shenandoah: The formal celebration of the 150th Anniversary of Stonewall Jackson's Shenandoah Valley Campaign ended this past Sunday but the battlefields are still there and there will be continuing reenactments and other special events for the next three years, so y'all come.In the spring of 1862, amidst the breathtaking beauty...

  • "Crazy"

    Throughout the 1990s, I lived near Baltimore, Maryland. Since I was a pre-schooler, my parents had lived in Charlotte, North Carolina. When I lived in Maryland, I made relatively frequent trips between Maryland and North Carolina. Usually, I took a shortcut from Frederick, Maryland to Interstate-81 just south of Winchester but when I was not racing...

  • Visit nearby Harpers Ferry, West...

    Harper's Ferry, at the border of Virginia, Maryland, and West Virginia, and at the confluence of the Potomac and Shenandoah Rivers, was a strategic Civil War location with lots of history. Long before the war, Harper's ferry was established as a manufacturing and transportation center, as the US Armory and Arsenal was established in 1799. In the...

  • Shenandoah River and Valley

    The Shenandoah River runs 150 miles through western Virginia from Port Republic into the Potomac at Harpers Ferry. The lowest 20 miles of the river are in West Virginia, while the rest of the river and its tributaries flow through Virginia. Around Front Royal, the Shenandoah is famous for Canoeing and the city of Front Royal was named by the...

  • Shenandoah National Park

    When in Winchester, be sure to make the 30-minute side trip to Skyline Drive at Shenandoah National Park. The cost is $10 per car for one week of unlimited entry and exit. The feature of the park is Skyline Drive, a twisty, turny two-lane road that follows the ridge of the mountains providing countless breathtaking views to the east and west, along...

  • Old Town Winchester

    While Winchester has grown to some 25,000 people, the Old Town area is still a quaint small town that has lots of history and numerous businesses in focused on a small, old fashioned pedestrian mall. While the Loudoun Street Mall is the focus of Old Town, this area covers a four by four block area bordered by Washington, Fairfax, Clifford and Kent...

  • Civil War history of Winchester

    The Shenandoah Valley was a crucial battleground early in the American Civil War, and Winchester, at the most accessible point of the valley, was the scene of numerous major battles and smaller skirmishes from 1861 to 1864. The more significant battles include the First Battle of Kernstown and the First Battle of Winchester in 1862, the Second...

  • Winchester's George Washington era...

    The Virginia House of Burgesses chartered Winchester (as Frederick Town) in 1750, and George Washington arrived soon after to help survey the town's lands for England's Lord Fairfax. When General Edward Braddock crossed through Winchester on the way to Fort Duquesne in the French and Indian War, Washington joined the expedition as he was very...

  • Winchester's Pedestrian Mall

    Central Winchester has a great Pedestrian Mall the runs perhaps three blocks in the heart of the historical city center. On Loudoun Street it is completely blocked off two traffic, but cars are allowed on some of the side streets that are partially pedestrianized. This is the core business district of the historic area and it has numerous local...


Winchester Hotels

Winchester Restaurants

  • Good Home-Cooking Chain

    $13 as of July 2014. Bob Evans is a chain of restaurants that serve food from the farm. Kind of home-cooking style. My waiter, Vonte, was better than average. Nice family atmosphere, with good food and decent portions. Hours are 6 AM to 10 PM Monday through Saturday, and 6 AM to 9 PM on Sunday. Chicken Pot Pie.

  • Good American Chain

    $10 as of July 2014. Perkin's is a restaurant/bakery chain. The décor is fairly nice and the atmosphere family related and informal. Service was good and the food decent enough. Hours are 6 AM to 10 PM daily. Cajun Tilapia or anything baked!

  • Midway at Weekend in the Park

    The midway at Weekend in the Park.Food is so much better when you eat it outside with the ones you love. And you don't get much more "American" than at a local festival like this. Giant turkey legs, pizza, grilled sausage & onions, barbecue, fries (not the place to be if you are on a diet!). Funnel cake! It's fried, it's doughy, it's covered with...

  • Brewbakers bar and restaurant

    On Valentines Day 2009, LHenne1 and I sort of stumbled upon Winchester's historic downtown without hotel or dinner reservations... Oops. Our hotel fiasco is described in another tip; luckily we were more fortunate on our restaurant pick despite seeing several downtown places with "reservations only" signs in the windows. As we wandered down Loudoun...

  • Piccadilly Grill

    On a recent Sunday we wandered around town for about 30 minutes, finding almost nothing open before finally settling on the tiny diner called the Piccadilly Grill. It is located just off the Pedestrian Mall in central Winchester. We entered the front door and were greeted by a thin veil of smoke and the awkwardness of seeing just 10 or 12 stools,...

  • The most original restaurant in town.

    Patsy's Pastry Pizzas has a unique atmosphere that makes you feel as if you are eating in someone's dining room. It is comfortable and inviting. The food is always great, consisting of the best salads in town, fantastic homemade soups, and an unbelievable variety of specialty pizzas.The service is friendly. I recommend this restaurant to everyone...


Winchester Nightlife

  • Ewingjr98's Profile Photo

    V2 Piano Piano Bar & Lounge

    by Ewingjr98 Updated Feb 15, 2009

    V2 Piano Piano Bar & Lounge is attached to the Village Square Restaurant (get it V2 like Village Squared?) and was opened in 2004. This is a nice, classy, and popular local hangout for the middle aged crowd ranging from about around 35 to 55 years old. The front area is small and cozy with numerous couches, soft chairs and love seats. It also has a piano in the corner by the front door, with live music.

    We stopped in for just 30 or 40 minutes and enjoyed a beer and a glass of pinot noir for about $12. During our stay we were at first impressed by the well-dressed and somewhat sophisticated clientele, then we started chuckling as we realized how drunk most of these people were by about 10pm. We saw guys dancing to the music in their heads, other guys almost knock chairs over as they stood up, and a few people yelling obscenities up and down the street as they left the bar.

    While we stuck with drinks, other people at the bar were enjoying the pizza and other light dishes such as crab cakes, hummas, sandwiches, and oysters that range from $7 to $19.

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Winchester Shopping

  • Find your Treasures here!

    This consignment shop is located right on the edge of the Winchester Walking Mall. The owner is Deb, aka VT member Dlee. She has a good sized shop loaded with treasures. Deb takes items of all kinds - antiques, clothes, things for your home, etc. on a 30 day consignment.

  • Shop in Quaint Downtown Winchester

    This is a good place to describe how delightful downtown Winchester really is.There are many, many nice little shops and quite a few buildings that are on the National Historic Register. It is all authentic. There are assorted bagel shops, bakeries, antiques shops, furniture stores and even the Post Office on the main street. There are quite a few...

  • Winchester Hotels

    31 Hotels in Winchester

    1 Reviews

Winchester Local Customs

  • Handley Regional Library

    Take a few minutes to step into the Handley LIbrary. It's a beautiful place. After our trip through Imperial Europe I now realize the dome on the library looks incredibly like the architecture in the old Hapsburg Empire. Inside, the Stewart Bell Jr. Archives Room offers an archive library for people looking for information about Frederick...

  • Watch out for large creatures...

    Watch out for large creatures lurking about. This guy is from a local fruit orchard, Hill High, where you can pick apples and peaches and pumpkins and . . .

  • Don't Get Carried Away

    The fun might just sweep you off your feet. This photo is of my niece doing a flip on the bungee thingy they had at this year's festival. For $5 you got to bounce around for 2 minutes on these giant rubber bands. Lots of people, from little kids to adults old enough to know better, were doing it.


Winchester Warnings and Dangers

  • Don't Overdo It

    The weekend just might sap all your strength! (OK, so this is just an excuse for my other cat, Beta, to get onto the page . . .) But you'll feel like this after a full day of Apple Blossom fun.

  • Guard Your Funnel Cake

    Guard your funnel cake. No matter how much you love your family and they love you, they will try to eat all of your fried goodness. And don't get powdered sugar up your nose. :-)

  • Don't Forget Insurance

    If your current health insurance doesn't cover you while your abroad, you should consider getting international travel insurance just in case something should go wrong.

Winchester Off The Beaten Path

  • The POW - MIA Memorial

    This is a great Viet Nam POW and MIA memorial in the Jim Barnett Park. The granite memorial has the names of the POW/MIA s from Viet Nam engraved on it. Stone benches around it memorialize POW/MIA Vets from other conflicts. The U.S. flag, the flag of the commonwealth of Virginia, and the POW/MIAs fly behind the granite monument. The monument and...

  • The original home

    This little log cabin is located right behind the beautiful stone Hollingsworth House.It's included in the tour. It's been beautifully restored and preserved and has a nice little story.

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Winchester Sports & Outdoors

  • 807Wheaton's Profile Photo

    Recreation area in Winchester

    by 807Wheaton Updated Aug 13, 2006

    2.5 out of 5 starsHelpfulness

    Jim Barnett Park provides a big area for Little League Baseball teams to play ball in the summer months. The building in this picture has a very nice indoor pool that is open year round for recreation. They offer senior rates of $2 a swim.

    Recreation building at Jim Barnett Park Pool area at the Recreation Building

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Winchester Favorites

  • soccergrrl's Profile Photo

    Weekend in the Park

    by soccergrrl Written Aug 25, 2002

    1.5 out of 5 starsHelpfulness

    Favorite thing: Go to Weekend in the Park, on the last days of the Apple Blossom Festival. It's a huge fair set up in Winchester's beautiful park. There are rides, games, a craft show, and TONS of really delish and terrible for you foods!

    Fondest memory: This has gotten to be a tradition in my family, and so Apple Blossom is my favorite time to be in Winchester.

    The Gang

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