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Top recommendations from locals

From sightseeing to hidden gems, find out what makes the city unique with the help of the locals who know it best.

Museum
“Museum & plantation home showcasing 18th-century art, a mini-house collection & regional history. ”
  • 14 locals recommend
Point of Interest
“Comedy shows, live music, food and drink. Check out their entertainment schedule.”
  • 5 locals recommend
Park
“Things to do for the whole family including running trails, disc golf, fitness facilities, with an outdoor pool (summer) and indoor pool. We provide you with the up to date calendar.”
  • 5 locals recommend
Miscellaneous Shop
“Downtown walking mall, has a large variety of great restaurants and shops. ”
  • 7 locals recommend
Bakery
“Freshly made in-house biscuts, local fried apples, and some of the best BBQ ever! ”
  • 5 locals recommend
Bar
$$
“Great atmosphere, live music, great food and drinks. Always lively on the weekends. Trivia Nights.”
  • 8 locals recommend
Museum
“Spark curiosity & inspire learning through exploration & creative play ! All ages will discover playful learning through hands-on, interactive exhibits at the Shenandoah Valley Discovery Museum! Discover the fun ... birthday parties for all ages, after hours rentals, overnights in the museum, summer camps June-August, School Field Trips & Programs! Open year around - Tues-Sat 9a-5p, Sun 1-5p, Mon -Closed!”
  • 6 locals recommend
Museum
“George Washington started his professional career in Winchester as a Land Surveyor. His office here (also known as the Adam Kurtz House, built 1757) was used during construction of Fort Loudoun.”
  • 4 locals recommend
Bar
“This restaurant boasts 50 craft beers along with 50 gourmet burgers. They have "beer flights" and the burgers are a great deal with a healthy side of fries for around $10.00”
  • 6 locals recommend
Bar
“Fish & chips! Among other authentic- English pub fare. Impressive beer selection. Has a "public hall" feel downstairs, cushy chairs on the landing upstairs. ”
  • 4 locals recommend
Café
“Great owner, cool vibe and some of the best coffee in town, and there are lots. Plus, vintage interiors and records and occassionally live music!”
  • 4 locals recommend
Restaurant
$$
“The de facto standard for excellent Thai in Winchester--everyone I know agrees they are great, with generous portions, friendly service, and a kid-favorite free dessert "smile". This is located on the walking mall though there is a 2nd location on Pleasant Valley which is equally good, just more of a strip mall experience. ”
  • 5 locals recommend
Grocery or Supermarket
“Sadly, there is no walking to the grocery from Wickham House, not yet anyway. Until we get a WholeFoods (or a Wegman's...or a Trader Joe's), there is Martin's. It's basically a big Giant Foods. The produce is good, if pricey. There are several locations. This is the one closest to the University. ”
  • 2 locals recommend
Museum
“ Home About Us Tour Schedule Tour Guidebook Tickets Photos Pressroom Contact Winchester Date Saturday April 27, 2019 Time 10 a.m. to 5 p.m. Host The Little Garden Club of Winchester and Winchester-Clarke Garden Club Winchester is the oldest city west of the Blue Ridge Mountains. Located in its downtown, this tour includes access to four stately private homes that showcase the charm and rich history of the area. George Washington worked there as a surveyor at age 16. Incredibly, the city changed hands over seventy times during the Civil War. Among the featured properties are an antique-filled beauty, a grand in-town estate situated on four acres, and two historic homes located on the”
  • 3 locals recommend
Miscellaneous Shop
“The old town walking mall is great for shopping, restaurants, bars, and is close to the residence. There is a parking garage on site and you can walk to all the different shops and restaurants. ”
  • 3 locals recommend