Winchester Guidebook

Tricia
Winchester Guidebook

Food scene

Authentic cuisine and awesome portions on the downtown walking mall.
21 locals recommend
Taste Winchester History
149 N Loudoun St
21 locals recommend
Authentic cuisine and awesome portions on the downtown walking mall.
Pizza and pasta on the walking mall, but ask the host about visiting the brewery upstairs. It's a local secret.
14 locals recommend
Roma Old Town Wood Fired Pizzeria
21 N Loudoun St
14 locals recommend
Pizza and pasta on the walking mall, but ask the host about visiting the brewery upstairs. It's a local secret.
British fare including fish and chips and mushy peas. A great pub offering, too, and axe throwing upstairs. Yes, axe throwing. : )
20 locals recommend
Union Jack Pub & Restaurant
101 N Loudoun St
20 locals recommend
British fare including fish and chips and mushy peas. A great pub offering, too, and axe throwing upstairs. Yes, axe throwing. : )
An upscale dining experience on the downtown walking mall. Check out their Sunday brunch!
13 locals recommend
Village Square Restaurant
103 N Loudoun St
13 locals recommend
An upscale dining experience on the downtown walking mall. Check out their Sunday brunch!
"Grab your morning coffee here on the downtown walking mall. A super fun coffee shop."
10 locals recommend
Hideaway Café
141 S Loudoun St
10 locals recommend
"Grab your morning coffee here on the downtown walking mall. A super fun coffee shop."
"Just yum. A little out of the way if you're downtown, but you can DoorDash."
Everest Restaurant
419 Gateway Drive
"Just yum. A little out of the way if you're downtown, but you can DoorDash."
Another one you can walk to. Fantastic wood-fired pizzas. Pup-friendly on the patio. Try the Kung Pao Cauliflower as an appetizer.
13 locals recommend
Oak Stone Craft Pizza and Bar
1000 Valley Ave
13 locals recommend
Another one you can walk to. Fantastic wood-fired pizzas. Pup-friendly on the patio. Try the Kung Pao Cauliflower as an appetizer.
"A fun browsing experience. Grab some Virginia-fresh produce and products here."
Virginia Farm Market
1881 N Frederick Pike
"A fun browsing experience. Grab some Virginia-fresh produce and products here."
"A local, long-time favorite on the downtown walking mall."
16 locals recommend
El Centro
1 N Loudoun St
16 locals recommend
"A local, long-time favorite on the downtown walking mall."
"Not sure what you want to eat? You won't be disappointed here at this downtown walking mall go-to. Pup-friendly on the patio."
6 locals recommend
Water Street Kitchen
2 S Loudoun St
6 locals recommend
"Not sure what you want to eat? You won't be disappointed here at this downtown walking mall go-to. Pup-friendly on the patio."

Wineries/Breweries

Tasty beers no matter what you choose. Pup-friendly, too!
13 locals recommend
Broken Window Brewing Co.
14 W Boscawen St
13 locals recommend
Tasty beers no matter what you choose. Pup-friendly, too!
"Beautiful historic home and winery just outside of Winchester, and it's said to be haunted. Enjoy the spirits either way. Live music on the weekends."
26 locals recommend
Valerie Hill Vineyard & Winery
1687 Marlboro Rd
26 locals recommend
"Beautiful historic home and winery just outside of Winchester, and it's said to be haunted. Enjoy the spirits either way. Live music on the weekends."
"Not beer. Not wine. Hard cider, appropriately in the Apple Capital."
17 locals recommend
Winchester Ciderworks
2504 N Frederick Pike
17 locals recommend
"Not beer. Not wine. Hard cider, appropriately in the Apple Capital."
"Ask the host to head to the brewery upstairs and he or she will show you the secret door. Try the Pizza Bier or Gen 2."
14 locals recommend
Roma Old Town Wood Fired Pizzeria
21 N Loudoun St
14 locals recommend
"Ask the host to head to the brewery upstairs and he or she will show you the secret door. Try the Pizza Bier or Gen 2."
"Rustic, relaxed charm - a best-kept-secret alternative to commercial, crowded wineries."
16 locals recommend
Aspen Dale Winery at the Barn
11083 John Marshall Hwy
16 locals recommend
"Rustic, relaxed charm - a best-kept-secret alternative to commercial, crowded wineries."
Upscale food and wine on the downtown walking mall.
6 locals recommend
The Wine Room at Taylor Pavilion
120 North Indian Alley
6 locals recommend
Upscale food and wine on the downtown walking mall.
Great new addition to downtown Winchester with indoor and outdoor seating, and fantastic menu.
Vibrissa Beer
10 North Kent Street
Great new addition to downtown Winchester with indoor and outdoor seating, and fantastic menu.
A little out of the way from Winchester, but the view makes the trip worth it. Don't like beer? Visit the nearby winery - same view, but with wine.
82 locals recommend
Dirt Farm Brewing
18701 Foggy Bottom Rd
82 locals recommend
A little out of the way from Winchester, but the view makes the trip worth it. Don't like beer? Visit the nearby winery - same view, but with wine.

Sightseeing

"100% perfect for the littles on the downtown walking mall."
34 locals recommend
Shenandoah Valley Discovery Museum
19 W Cork St
34 locals recommend
"100% perfect for the littles on the downtown walking mall."
"Just around the corner from your airbnb, visit the home of the country music legend famous for her hits "Crazy," "Sweet Dreams," and "Walking After Midnight" just to name a few."
17 locals recommend
Patsy Cline Historic House
608 S Kent St
17 locals recommend
"Just around the corner from your airbnb, visit the home of the country music legend famous for her hits "Crazy," "Sweet Dreams," and "Walking After Midnight" just to name a few."
"Just outside Winchester, an easy hike to an amazing view of the Shenandoah Valley."
7 locals recommend
Bear's Den Scenic Lookout
7 locals recommend
"Just outside Winchester, an easy hike to an amazing view of the Shenandoah Valley."
"Revisit your childhood or treat your own kids to this step-back-in-time roadside attraction."
17 locals recommend
Dinosaur Land
3848 Stonewall Jackson Hwy
17 locals recommend
"Revisit your childhood or treat your own kids to this step-back-in-time roadside attraction."
"Revolving art exhibits, live outdoor music, beautiful gardens, plus family-friendly walking trails."
72 locals recommend
Museum of the Shenandoah Valley
901 Amherst St
72 locals recommend
"Revolving art exhibits, live outdoor music, beautiful gardens, plus family-friendly walking trails."
"Get your seasonal fun and live music here."
13 locals recommend
West Oaks Farm Market South and Event Center
4305 Middle Rd
13 locals recommend
"Get your seasonal fun and live music here."
"One of the few remaining drive-in movie theatres in the United States. Check it out!"
25 locals recommend
Family Drive-In Theatre
5890 Valley Pike
25 locals recommend
"One of the few remaining drive-in movie theatres in the United States. Check it out!"
"Visiting the area? Get all the information on all there is to do and see here."
6 locals recommend
Winchester-Frederick County Convention & Visitors Center
1400 S Pleasant Valley Rd
6 locals recommend
"Visiting the area? Get all the information on all there is to do and see here."
"A fun browsing experience"
Blue Peacock Antiques
116 N Loudoun St
"A fun browsing experience"
Stop by this gallery for incredible Winchester paintings, prints, notecards and ornaments, plus much more.
Eugene B. Smith Gallery & Custom Framing Studio
25 North Loudoun Street
Stop by this gallery for incredible Winchester paintings, prints, notecards and ornaments, plus much more.