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. Known as the “Apple Capital”, surrounded as it is by vast orchards and constituting one of the largest apple export markets of the nation and the largest producing area in Virginia, Winchester is rich in history and economic breadth. Downtown Winchester hosts an expansive historic district as well as over 30 places to eat and 50 retail shops. Festivals, live music, and patio seating enliven the Old Town Pedestrian Mall (Loudoun Street) throughout the year. With endless shopping, dining, and recreational options right at your doorstep, local charm and convenience combine to create the perfect living area. Get caught up in the activity of one of the many yearly festivals and happenings, or simply relax and enjoy the amazing scenic views from the comforts of your new apartment home.
Upcoming Events in Winchester
Are you looking for something fun to do in Winchester, Virginia? If so, you’re in luck! As the oldest city in the Commonwealth of Virginia, Winchester is brimming with events throughout the year. From concerts and festivals to seasonal activities like ice skating and apple picking, Winchester has something for everyone. Living at Jubal Square Apartments puts all of these events just outside your door! Get out into your local community and explore all that historic Winchester has to offer! We invite you to check out Winchester’s upcoming events:
West Oaks Fall Harvest Festival
Plan your trip to West Oaks Farm for apple and pumpkin picking, corn maze, hayrides, and more on the farm celebrating the Fall Harvest!
Fall Pumpkin Harvest Festival
Celebrate fall at Great Country Farms in Northern VA with pumpkin picking, a corn maze, cider donuts, pig races, and plenty of family fun.
Haunted History Ghost Tours
Explore Winchester’s haunted past with ghost tours each October. Historic streets come alive with chilling tales and local lore.
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 Jubal Square Apartments 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
- 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
- Richards Fruit Market
- Roma Wood Fired Pizzeria
- Taquería Guadalajara
- Sabai Thai Winchester
- 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
Jubal Square 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.
- Adult Egg Hunt
- Antique & Modified Car Show
- Celebración of Winchester
- Fall Pumpkin Harvest Festival
- First Fridays in Winchester
- FredCo Eats Restaurant Week
- Frederick County Fair
- Haunted History Ghost Tours
- Healing Field of Honor
- Holiday Parade & Tree Lighting
- Hop Blossom Craft Beer Festival
- July 4th Celebration at Sherando Park
- Juneteenth Celebration
- Kite Fest
- MSV: Plant Sale
- National Jazz Workshop
- Old Town New Year’s Eve Festival
- 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
- Walking in a Winter Wonderland
- West Oaks Fall Harvest Festival
- Winchester Celtic Fest
- Winchester Greek Festival
- Winchester Historic Garden Week
- Winchester Restaurant Week
- Wings & Wheels at Winchester Regional Airport
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...
S. Sawin
Living here has been a great experience! Overall, it’s been a great value for the price and the complex and grounds are really nice. The maintenance team has been super responsive the few times I’ve had any issues.
