Winchester,
Winchester is a charming city located in the state of Virginia, United States. It is known for its picturesque scenery, historic architecture, and vibrant community culture. Winchester boasts a variety of recreational opportunities, such as hiking trails, parks, and outdoor events.
The city also features a thriving downtown area with unique shops, restaurants, and cultural attractions.
Places to visit
Day plans
Spend a day exploring around
Explore Historic Downtown
morning:Start your day by exploring the rich history of Winchester at the Museum of the Shenandoah Valley. Afterward, grab a delicious breakfast at Village Square Restaurant.
afternoon:Visit the Old Town Winchester pedestrian mall for a relaxing stroll and some shopping. Don't miss a late lunch at Roma Old Town Wood Fired Pizzeria.
evening:For a delightful night-out, head to Winchester Brew Works for some craft beer and live music.
Outdoor Adventure
morning:Embark on a scenic hike at the Abrams Creek Wetlands Nature Trail. Afterward, refuel with a hearty brunch at Steamy's Cafe.
afternoon:Spend the afternoon kayaking on the tranquil waters of Lake Frederick before enjoying a picnic by the shore.
evening:For a fun night-out, head to Piccadilly Public House for delicious food, drinks, and live entertainment.
History and Culture
morning:Start your day with a visit to the Stonewall Jackson's Headquarters Museum to delve into Civil War history. Then, savor a delightful brunch at Hideaway Cafe.
afternoon:Explore the historic Belle Grove Plantation and take a leisurely stroll through the beautiful gardens. Enjoy a late lunch at the charming Nana's Irish Pub.
evening:For a vibrant night-out, head to Bright Box Theater for live performances and a lively atmosphere.
Wine and Dine
morning:Begin your day with a scenic drive to Valerie Hill Vineyard & Winery for a fascinating winery tour and tasting experience. Enjoy a lovely brunch at the vineyard's bistro.
afternoon:Discover the culinary delights of Winchester with a food tour, tasting local specialties at various eateries. Savor a late lunch at Village Square Restaurant.
evening:Indulge in a charming night-out with a visit to Violino Ristorante Italiano for delectable Italian cuisine and fine wine.
Winchester Famous Food
Must-Try local dishes
Shenandoah Apple Cake
A delectable cake made with locally-grown apples, cinnamon, and a hint of nutmeg, often enjoyed with a dollop of freshly whipped cream. Best found at the Winchester Farmer's Market.
Must-Try!
Southern Fried Chicken
A southern classic featuring crispy, juicy chicken served with sides like mashed potatoes and collard greens. Look for this dish at Bonnie Blue Southern Market & Bakery.
Shenandoah Valley Apple Dumplings
Flaky pastry filled with sweetened apples, cinnamon, and sugar, often served with a scoop of vanilla ice cream. Indulge in this delightful treat at the Amherst Street House Restaurant.
Food Markets & Street Food
A food market and street food guide
Winchester Farmer's Market
This vibrant market offers an array of fresh produce, local cheeses, baked goods, and ready-to-eat treats such as homemade tamales and artisanal popsicles.
Courtyard Barbecue
Discover mouthwatering BBQ delights at the Courtyard Barbecue food truck, where you can feast on slow-smoked meats and savory sides in a bustling street food setting.
Things to do in Winchester
Unique local experiences...
Pet sitters in Winchester
Relax and unwind while your furry friend enjoys making a new companion!