Winchester Travel Guide

  Court House and Feltner Building
by Ewingjr98
 
  • 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
  • The Old Court House -- now a Civil War museum
      The Old Court House -- now a Civil War...
    by Ewingjr98
  •   Things to Do
    by Ewingjr98
 

Explore Winchester

Things to Do  

Civil War Sesquicentennial

Civil War Sesquicentennial, Winchester

 etfromnc Says:  A Whirlwind in the Shenandoah: The 150th Anniversary of Stonewall Jackson's Campaign in the Shenandoah Valley of VirginiaIn the spring of 1862, amidst the breathtaking beauty of the Shenandoah Valley, Confederate Gen. Thomas J. "Stonewall" Jackson conducted one of the most... 

"Crazy"

"Crazy", Winchester

 etfromnc Says:  Throughout the 1990s, I lived near Baltimore, Maryland. Since I was a pre-schooler, my parents 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,... 

Visit nearby Harpers Ferry, West Virginia

Visit nearby Harpers Ferry, West Virginia, Winchester

 Ewingjr98 Says:  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... 

Shenandoah River and Valley

Shenandoah River and Valley, Winchester

 Ewingjr98 Says:  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... 

Shenandoah National Park

Shenandoah National Park, Winchester

 Ewingjr98 Says:  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... 

Old Town Winchester

Old Town Winchester, Winchester

 Ewingjr98 Says:  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... 

Civil War history of Winchester

Civil War history of Winchester, Winchester

 Ewingjr98 Says:  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... 

Winchester's George Washington era history

Winchester's George Washington era history, Winchester

 Ewingjr98 Says:  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... 

Winchester's Pedestrian Mall

Winchester's Pedestrian Mall, Winchester

 Ewingjr98 Says:  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... 

Winchester's Old Court House & Feltner Building

Winchester's Old Court House & Feltner Building, Winchester

 Ewingjr98 Says:  The historic Winchester Court House preexists the Civil War, but two previous court houses also share in the town's history. The first court house was constructed in 1741, and is considered the first courthouse ever constructed beyond the Blue Ridge mountains. The second... 

Hotels  

The George Washington Hotel

 2 Reviews and 144 Opinions  We tried the George Washington when we took my daughter for a college orientation trip --thought... 

Wingate Inn Winchester

 1 Review and 50 Opinions  We have your basic hotels here. Days Inn, Holiday Inn but this is a newer hotel that is very nice at... 

Restaurants  

You Name it, They Got it (Almost): Midway at Weekend in the Park

You Name it, They Got it (Almost): Midway at Weekend in the Park, Winchester

 soccergrrl Says:  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... 

Brewbakers bar and restaurant

Brewbakers bar and restaurant, Winchester

 Ewingjr98 Says:  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... 

Piccadilly Grill

Piccadilly Grill, Winchester

 Ewingjr98 Says:  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... 

Patsy's Pastry Pizzas: The most original restaurant in town.

Patsy's Pastry Pizzas: The most original restaurant in town., Winchester

 jsc110348 Says:  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... 

Nightlife  

V2 Piano Piano Bar & Lounge

V2 Piano Piano Bar & Lounge, Winchester

 Ewingjr98 Says:  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... 

Shopping  

Fabulous Finds: Find your Treasures here!

Fabulous Finds: Find your Treasures here!, Winchester

 807Wheaton Says:  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. 

Bakeries and Antiques: Shop in Quaint Downtown Winchester

Bakeries and Antiques: Shop in Quaint  Downtown Winchester, Winchester

 807Wheaton Says:  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,... 

Local Customs  

Handley Regional Library

Handley Regional Library, Winchester

 807Wheaton Says:  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... 

Off The Beaten Path  

The POW - MIA Memorial

The POW - MIA Memorial, Winchester

 807Wheaton Says:  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... 

Sports & Outdoors  

Recreation area in Winchester

Recreation area in Winchester, Winchester

 807Wheaton Says:  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. 

 
Explore Deeper into Winchester

The Place

Plan a Winchester vacation with reviews, tips and photos posted by real travelers and Winchester locals

Experience Winchester
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The People

42 Members Live Here
 
Advice from the Locals
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 Winc City Virginia - Hola! Ok so if you ever end up coming to Winchester (Winc City for kicks) here is the low down. Small town in the suburbs of northern va but we are growing! Very nice spot to settle, not so nice if... 

42 members live in Winchester

 

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Top Winchester Writers

1

Visit Winchester in the Shanandoah Valley

807Wheaton profile photo

 About two years ago we discovered that my husband's great-great grandfather was born in Winchester, Virginia. Shortly after that our daughter's husband was transferred from Charlotte to Winchester. We... 

2

More history than I expected--Winchester

Ewingjr98 profile photo

 I've got some interesting experiences in Winchester. I'd love to share with you the 12 tips I've written, the 54 photos uploaded, and 0 travelogues I've created. 

3

A Big Apple

chewy3326 profile photo

 Somehow, Winchester, Virginia qualifies much more for the name of "The Big Apple" than New York City ever would. Winchester is Virginia's capital of apples, with numerous orchards scattered throughout... 

4

Winc City Virginia

nena2997 profile photo

 Hola! Ok so if you ever end up coming to Winchester (Winc City for kicks) here is the low down. Small town in the suburbs of northern va but we are growing! Very nice spot to settle, not so nice if...... 

5

Apple Blossom Festival, 2002

soccergrrl profile photo

 Hello, I'm Alpha, one of Soccergrrl's cats. As promised, here are some photos from the Shenandoah Apple Blossom Festival 2002 (May 4-5). Apples are an important crop in the area, and this is the time... 

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