A Relaxing, Fun-Filled Trip to Winchester

Take a break from your metropolitan busyness and bask in the tranquility of the country.

By Shelby Robinson

Winchester Courthouse
Winchester Courthouse. Photo courtesy of Jon Bilous/Shutterstock.com.

When you get sick of the fast-paced, metropolitan lifestyle, its nice to know that there are places you can go without going too far. Winchester is one of those places. Nestled only about 70 minutes from Fairfax, Winchester offers the convenience of locality and the comfort and charm of a small town. Winchester’s many local restaurants and shops and rich history offers a unique experience regardless of what you’re looking for.


Eating and Drinking in Winchester 

Most of the restaurants in Winchester are locally-owned, providing the hometown feel mixed with wealth of culinary choices.

Sona Restaurant

Serving authentic North Indian cuisine, Sona is a great choice for many specialty and signature dishes. Shiv Kumar, the founder and head chef of Sona, began cooking as a hobby, but decided to open a restaurant after encouragement from his friends and family. Sona is open only for lunch and dinner, so be sure to check for restaurant hours on the Sona website. 2900 Valley Ave. Winchester, 22601.


Union Jack Pub & Restaurant

A local favorite, many people come to Union Jack for the legendary fish & chips and wide variety of beer on tap. Union Jack is a historical landmark, residing in the Union Bank building that was originally built in 1878. Open from 11 a.m. daily until 1 a.m., 2 a.m. Saturdays. 101 N. Loudoun St.,Winchester. unionjackpub.com


Union Jack Pub & Restaurant
Photo courtesy of Union Jack Pub & Restaurant.



Photo courtesy of Village Square Restaurant

Village Square Restaurant & V2 Piano Bar and Lounge

With a menu as interesting as the historical building, it’s hard to go wrong at Village Square Restaurant & V2. They serve everything from falafel to Ahi Tuna and make a wide variety of classic and signature cocktails. Open from 11:30 a.m, closing hours vary. 103 N. Loudoun St., Winchester. villagesquarerestaurant.com


Violino Restaurante Italiano

At Violino, you can get authentic Italian food without leaving historical down town Winchester. Violino is open every day except Sunday, hours vary. 181 N. Loudoun St., Winchester.  violinorestaraunte.com


Wok Zone

Wok Zone is a highly rated Asian-Fusion restaurant serving a variety of gourmet Thai, Chinese, and Japanese foods. Wok Zone is closed on Sundays and open from 11 a.m.- 9 p.m. or 9:30 p.m. Monday through Saturday. 179 Kernstown Commons Blvd, Winchester. wokzone.com


Where to Stay in Winchester

Aloft Winchester

Aloft’s modern layout, bright colors, beautiful indoor pool, live concerts and notorious W XYZ Bar create a hip environment while also being fun for families. 1055 Millwood Pike, Winchester. Visit their website for booking information and prices.


Old Waterstreet Inn

If you are more in the mood for an old-fashioned, classy bed-and-breakfast, the Old Waterstreet Inn might be for you. A historical federal-style brick home, the Old Waterstreet Inn is only two blocks from the down town strip. This great location puts you only a short walk from the restaurants, shops and bars. 217 W. Boscawen St., Winchester. Visit their website for booking information and prices.

The Country Inn at High View

What it lacks in convenience to the downtown mall, the County Inn makes up for in spaciousness. The Country Inn is situated on 200 acres of land and sits atop a hill with a beautiful view of the mountains. The Country Inn at High View is about 20 minutes driving from the down town mall. Carpers Pike, High View, WV. Visit their website for booking information and prices.


Shops and Boutiques

Blue Plate Books

Take the time to browse the well-stocked shelves of Blue Plate Books and find a great read for a relaxing vacation. Blue Plate Books is open daily from 11 a.m. to 7 p.m. 2257 Valley Ave., Winchester. 


Blue Plate Books
Photo courtesy of Blue Plate Books.


Creekside Station

If you want to indulge in some retail therapy, Creekside Station is the place to go. With a variety of national chains as well as local boutiques, you are sure to find something you love. 106 Creekside Lane,
Winchester. Visit their website for a complete list of operating hours and store directory.


Eugene B. Smith Gallery

Whether you feel like admiring some watercolor paintings or you’re in the market to buy, the Eugene B. Smith Gallery is the place to go. 25 N. Loudoun St., Winchester. Open every day, for hours visit the website.

 Eugene B. Smith Gallery
Photo courtesy of Eugene B. Smith Gallery.


Posh Pets Boutique

While you’re in Winchester, don’t forget to pick something up for the furry companion you left at home. Posh Pets Boutique has everything your little one could want and more. 16 S. Loudoun St.,  Winchester. Open every day, for hours visit the website


Travel Deals and Steals

Booking your weekend getaway to Winchester right now has a few financial advantages.

– Because it is still considered “off season” (till late March-May depending on the spot), it is $20-50 less per night in hotels and bed & breakfasts.

– The Country Inn has a few deals going right now. If you book in the next few weeks you will get two free tickets to a few historical Civil War spots including Stonewall Jackson’s Headquarters, George Washington’s Office Museum and Abrams Delight located in Winchester, VA.

Travel Tip

If you choose to stay at one of the Bed & Breakfasts listed above, make sure to call at least a few weeks ahead of time. These Bed & Breakfasts each only have three to five rooms so they fill up quickly. If you do decided to plan a spontaneous trip, booking a hotel might be easier and more guaranteed to have room.