Things to Do in Winchester
Right outside your door…
Included in Kiplinger’s 2015 list of “10 Great Places to Retire”, Winchester, Virginia, provides the perfect combination of small-town allure and big-city amenities. Life in Winchester offers a mix of old and new: historical landmarks and homes, including one belonging to Winchester native and country music legend Patsy Cline, sit alongside contemporary galleries, craft breweries, and shops. Winchester is also home to the Apple Blossom Festival each spring, thanks to the farms and orchards in the surrounding countryside. There’s always something to do in Winchester – find a wonderful escape for those seeking relaxation, outdoor adventure, or an opportunity to immerse themselves in the history and culture of the area. Enjoy scenic beauty, unique architecture, historical sites, and recreational activities right outside your apartment at the Local! Get caught up in the activity of one of the many yearly festivals and happenings, explore all the restaurants, shopping, and outdoor experiences Winchester and the surrounding area have to offer, or simply enjoy the comforts of your new apartment home.
Upcoming Events in Winchester
We invite you to check out Winchester’s upcoming events:
Patsy Cline Block Party
Celebrate the legacy of country music icon Patsy Cline at the Annual Patsy Cline Block Party in Winchester, VA. This free,...
Hungry for History Food Event
Explore the Shenandoah Valley’s culinary past with food tastings, history programs, and family-friendly events during Hungry for History.
Sunflower Festival
Enjoy sunflower fields and flower picking, local vendors, food trucks, games for the kids, Live music, and more!
Endless Options…
Winchester is a city bursting with possibilities: world-class shopping, quality entertainment, historic sites, excellent dining, and so much more! Use the information below to begin experiencing all that Winchester has to offer.
Dining in Winchester
Winchester is part of the Central Virginia region that has become very popular with gourmet enthusiasts and foodies across the nation. A wealth of nearby farms producing world-class meat, poultry, produce, nuts, and more make it easy to find local ingredients in Winchester cuisine. A wide variety of wineries, breweries, and farmers’ markets make it easy to create a gourmet menu at home as well. Your Winchester apartment at The Local allows you to explore the best of the Winchester dining scene. Find just a sampling of the many food options available in Winchester below:
- Arterra Wines
- Aspen Dale Winery
- Backroom Brewery
- Biscuits & Beans Cat Café
- Bluemont Vineyard
- Bonnie Blue
- Café Del Sol
- Carrabbas
- Charley’s Cheesesteaks
- Chop Stick Cafe
- Cracker Barrel
- El Sabor Latino
- Everest Indian Restaurant
- Glory Days Grill
- Great American Grill
- Hideaway Café
- Ichiban Japanese Steak & Seafood House
- IJ Canns
- It’s Just Wings
- James Charles Winery
- Mackintosh Fruit Farm
- Oishii Sushi & Ramen
- Old Town Cidery
- Papermill Restaurant
- Paisano’s Pizza
- Paradise Restaurant
- Peru’s Chicken
- Longhorn Restaurant
- Lost Mountain Vineyards
- Red Robin
- RdV Vineyards
- Richards Fruit Market
- Rinker Orchards
- Roma Wood Fired Pizzeria
- Sabai Thai Winchester
- Sonrise Daylily Farm
- Taquería Guadalajara
- Umbertos Pizza
- Union Jack Pub
- Village Square Restaurant
- Valerie Hill Winery
- Veramar Vineyard
- Violino Ristorante Italiano
- Virginia Farm Market
- Water Street Kitchen
Shopping in Winchester
The Local is conveniently located near downtown Winchester’s unique and diverse shopping scene, providing shoppers with a wide variety of wonderful choices. Below is a sampling of some of the best shopping near your Winchester apartment:
- Apple Blossom Mall
- Blue Peacock Antiques
- Blue Plate Books
- Blue Ridge Care Winchester Thrift Shop
- Creekside Gifts
- Delco Plaza
- Exotic Himalayan Handcrafts
- Foodmaxx
- Hobby Lobby
- Incredible Flying Objects
- John B. Hayes Tobacconist
- Kimberly’s
- Make Nest
- Martin’s
- Michelle’s Wigs & More
- Mountain Trails
- Old Town Winchester
- Plume House Vape Co
- Polka Dot Pot
- Posh Pets Boutique
- Sonrise Daylily Farm
- Target
- Thinker Toys
- Tin Top Art & Handmade
- Twice is Nice
- Virginia Farm Market
- Walmart Supercenter
- White House Country Store
- Winchester Book Gallery
- Winchester Farmers Market
Winchester Culture & Recreation
If you’re looking for a city that offers both culture and recreation in abundance, then Winchester, Virginia, is the place to be! Rich in art galleries, theaters, parks, and more, one could easily spend days exploring all that Winchester has to offer. We invite you to use these links to Winchester recreation and culture sites to plan your exploration – there are so many choices!
- Abrams Creek Wetlands Preserve
- Appalachian Trail Conservancy
- Bright Box Theater
- Candy Hill Campground
- Clearbrook Park
- Frederick County Parks
- Jim Barnett Park
- Northside Lanes
- Raven Rocks Hike
- Rocking S Ranch
- Shawnee Springs Preserve
- Shenandoah Valley Discovery Museum
- Rose Hill Park
- Sherando Park
- Sky Meadows State Park
- Winchester Little Theatre
- Winchester Recreation Center
Historic Sites in Winchester
Winchester is the oldest city in the Commonwealth of Virginia and offers a wide array of historically significant locations! Discover historic homes and buildings, museums and archives, Civil War locations and battlefields, and many more historic sites in and around Winchester.
Annual Events in Winchester
Explore all the vibrant attractions Winchester has to offer! This city provides something for everyone with fairs, food festivals, concerts, art shows, parades, events, recreational opportunities, and much more.
- Apple Harvest Festival
- Bluegrass on the Farm
- Fall Pumpkin Harvest Festival
- First Fridays
- FredCo Eats Restaurant Week
- Haunted History Ghost Tours
- Hop Blossom Craft Beer Festival
- Hungry for History Food Event
- July 4th Celebration at Sherando Park
- Kite Fest
- Leesburg Animal Park Christmas Village
- National Jazz Workshop
- New Year’s Eve Celebration
- Old Town Celtic Fest
- Patsy Cline Block Party
- Rockin’ Independence Eve
- Route 11 Yard Crawl
- Shenandoah Apple Blossom Festival
- Shenandoah Valley Apple Harvest Festival
- Sunflower Festival
- Thanksgiving Day 5K & Fun Run
- Trunk or Treat on Loudoun Street
- West Oaks Fall Harvest Festival
- West Oaks Farm Market: Adult Egg Hunt
- West Oaks Farm: Friday Night Concerts
- Winchester Historic Garden Week
- Winchester Old Town Winter Village
- Winchester Police Department Car Show
- Winchester Restaurant Week
Events & Activities in Winchester
Learn even more about some of our favorite local events from our blog! Check out these posts for more information:
What residents are saying...
C. Denby
Winchester is such a vibrant town, and The Local puts you right at the center of everything Winchester is famous for! It is truly a delight to find luxury apartments that are professionally managed in a location that is perfect for modern living. For those looking for an oasis amidst a sea of possibilities, The Local is a wonderful addition to an already enchanting place to live.
