Food Scene
Altstadt Winchester
136 S Loudoun StNumerous restaurants, shops and bars!
Best breakfast in town! Really cool inside of an old gas station. Has won many awards for their BBQ. Great specials for dinner on Friday & Saturday nights. Closes at 8pm so go early.
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Bonnie Blue Southern Market & Bakery
334 W Boscawen StBest breakfast in town! Really cool inside of an old gas station. Has won many awards for their BBQ. Great specials for dinner on Friday & Saturday nights. Closes at 8pm so go early.
Great burgers and brewery located on side street at end of Old Town!
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50/50 Taphouse
29 W Cork StGreat burgers and brewery located on side street at end of Old Town!
Great food! It is on side street at the end of Old Town mall.
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Cork Street Tavern
8 W Cork StGreat food! It is on side street at the end of Old Town mall.
Ichiban Japanese Steak & Seafood House
2058 South Pleasant Valley RoadYum!😋
El Centro
1 N Loudoun StGreat Mexican food and located in Old Town!
Great Italian food and located in Old Town!
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Roma Old Town Wood Fired Pizzeria
21 N Loudoun StGreat Italian food and located in Old Town!
My favorite Chinese restaurant for dine in or carry out. Unfortunately no delivery but definitely the best in Winchester! Owner is fantastic and they have been in business many years.
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Chinatown Restaurant
1085 Millwood PikeMy favorite Chinese restaurant for dine in or carry out. Unfortunately no delivery but definitely the best in Winchester! Owner is fantastic and they have been in business many years.
Another great diner for breakfast/brunch! Well known and loved by the Winchester community!
Papermill Place
2214 Papermill RdAnother great diner for breakfast/brunch! Well known and loved by the Winchester community!
Huge Farm Market where you can shop, have lunch and often has live entertainment!
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West Oaks Farm Market South and Event Center
4305 Middle RdHuge Farm Market where you can shop, have lunch and often has live entertainment!
Martin's Food
1950 S Pleasant Valley RdGrocery shopping! Very close to both homes.
Pizza & subs. Very close to the Colonial house but will also deliver to the Charmer.
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Anthony's Pizza
1855 Senseny RdPizza & subs. Very close to the Colonial house but will also deliver to the Charmer.
Winchester Spring Valley Market
2454 Northwestern TurnpikeA family favorite for fresh fruit & vegetables year around!
Pizza with a great outdoor patio area and located off Loudoun street near Old Town walking mall.
Pizzoco Pizza Parlor
501 N Loudoun StPizza with a great outdoor patio area and located off Loudoun street near Old Town walking mall.
Delicious food, best French dip sandwich I've ever had! A nice variety of foods and large patio to sit outside. They also have a bar!
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Oak Stone Craft Pizza and Bar
1000 Valley AveDelicious food, best French dip sandwich I've ever had! A nice variety of foods and large patio to sit outside. They also have a bar!
Now open...Subs, coffee and more with an owner wanting to give back to our veterans, how awesome!?!
Veterans Subs
621 West Jubal Early DriveNow open...Subs, coffee and more with an owner wanting to give back to our veterans, how awesome!?!
Great Italian food owned by a great friendly family! Located in Old Town.
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Violino Ristorante Italiano
181 N Loudoun StGreat Italian food owned by a great friendly family! Located in Old Town.
The Rancho Mexican Restaurant
2197 S Pleasant Valley RdGreat Mexican food and close to shopping!
Okinawa
Great Japanese food and sushi!
Great stop after a hike at Bears Den or just to hang out for the day for food, beer, and scenery!
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Bear Chase Brewing Company
33665 Bear Chase LnGreat stop after a hike at Bears Den or just to hang out for the day for food, beer, and scenery!
Who doesn't love a great waffle! Located in the quaint little town of Berryville.
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Cordial Coffee Co.
8 S Church StWho doesn't love a great waffle! Located in the quaint little town of Berryville.
Great new restaurant‐ Delicious food and friendly staff! Super close to Colonial getaway if you want to avoid crowds and traffic. I love it!
Poblanos Mexican Grill
Great new restaurant‐ Delicious food and friendly staff! Super close to Colonial getaway if you want to avoid crowds and traffic. I love it!
Highly recommended by a guest who attended a bridal shower here. Two locations, Berryville and Winchester!
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The Tea Cart
16 W Main StHighly recommended by a guest who attended a bridal shower here. Two locations, Berryville and Winchester!
My grandparents used to take me here for ice cream! If you need a sweet treat of soft serve ice cream, this is your spot. Located about a mile and a half away!
Dairy Corner
My grandparents used to take me here for ice cream! If you need a sweet treat of soft serve ice cream, this is your spot. Located about a mile and a half away!
Vineyards
James Charles Winery & Vineyard
4063 Middle RdVeramar Vineyard
905 Quarry RdHiking and sightseeing
Numerous easy trails, beautiful scenery and monuments along the way. Just a few minutes away! Easiest route is to stay on 7 and park behind Millbrook high school. You'll see parking just for the battlefield.
Third Battle of Winchester Trail
Third Battle of Winchester TrailNumerous easy trails, beautiful scenery and monuments along the way. Just a few minutes away! Easiest route is to stay on 7 and park behind Millbrook high school. You'll see parking just for the battlefield.
Beautiful scenery, nice trails and areas to picnic. About a 30 minute drive to get there.
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Shenandoah National Park, Front Royal Entrance Station
17157 Skyline DrBeautiful scenery, nice trails and areas to picnic. About a 30 minute drive to get there.
Nice views and easy trails. Located about 15 to 20 minutes from the house in Bluemont Va.
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Bears Den
18393 Blue Ridge Mountain RdNice views and easy trails. Located about 15 to 20 minutes from the house in Bluemont Va.
This is in West Virginia and well worth the 35 minute drive, so beautiful!
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Harpers Ferry
This is in West Virginia and well worth the 35 minute drive, so beautiful!
Easy to Moderate hike and stunning views at the top. Located on the Frederick County and Hampshire County line. About a 40 minute drive to get there. Totally worth it!
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Tuscarora Trail Eagle Rock Trailhead
324 Capon Springs GradeEasy to Moderate hike and stunning views at the top. Located on the Frederick County and Hampshire County line. About a 40 minute drive to get there. Totally worth it!
If you're up for a challenge and have about 4 hours to spare this is your hike. Nicknamed the "rollercoaster" as it is nearly 6 miles of a rocky up and down terrain both in an out. I would say it's a little on the more difficult side but I did enjoy it. Go for it! The views are worth it!
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Raven Rocks
If you're up for a challenge and have about 4 hours to spare this is your hike. Nicknamed the "rollercoaster" as it is nearly 6 miles of a rocky up and down terrain both in an out. I would say it's a little on the more difficult side but I did enjoy it. Go for it! The views are worth it!
Moderate rocky hike roughly 6.5 miles up and back with two beautiful overlooks. These two trails connect. Enjoy a beautiful taste of Maryland and just 45 minutes away!
Annapolis Rock Black Rock Cliff
11175 Baltimore National PikeModerate rocky hike roughly 6.5 miles up and back with two beautiful overlooks. These two trails connect. Enjoy a beautiful taste of Maryland and just 45 minutes away!
Kid fun!
Cool place for kids to learn and have some fun!
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Shenandoah Valley Discovery Museum
19 W Cork StCool place for kids to learn and have some fun!
Fun for the whole family especially great for kids in the fall- hayrides, corn maze, pick your own pumpkin, petting zoo and more! **Only open on weekends**
Hill High Farm
933 Barley LnFun for the whole family especially great for kids in the fall- hayrides, corn maze, pick your own pumpkin, petting zoo and more! **Only open on weekends**
Mac's Roller Rink
5030 Front Royal PikeRoller skating! Great fun for kids and adults!
Jim Barnett Park
Nice park for a picnic, walking trails, playgrounds for kids, and special events!
Sightseeing
Nice walking trails
Fun for the whole family! Lots of trails to walk, explore and learn!
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Museum of the Shenandoah Valley
901 Amherst StFun for the whole family! Lots of trails to walk, explore and learn!
Shopping
The Valley Bride
244 N Cameron StGreat place to shop for weddings! Morgan the owner is fantastic!