Planning a visit to James Charles Winery & Vineyard? Make Winchester, Virginia your weekend home base. It’s close to the winery, easy to explore, and centered around a lively historic downtown that feels like a smaller, more relaxed Alexandria: brick architecture, local boutiques, great restaurants, and a walkable main strip where you can park once and wander.
Old Town’s centerpiece is the Loudoun Street Pedestrian Mall, a car-free stretch lined with shops, patios, and places to grab a bite before (or after) your winery day. Learn More
Where to stay in Winchester
The George Washington, a Wyndham Grand Hotel
If you want a true weekend-getaway feel, book The George Washington. It’s a historic, grand-style hotel right in the heart of Old Town—ideal if your plan is dinner downtown, a post-meal stroll, and an easy morning coffee walk before heading out to the winery. Visit Website
Hilton Garden Inn Winchester
For comfort and convenience (plus easy parking), Hilton Garden Inn Winchester is a dependable choice—especially if you like straightforward amenities and a simple drive to both Old Town and James Charles Winery & Vineyard. Visit Website
Where to eat in Winchester
T.T. Wall’s Kitchen & Bar
A must for food lovers, T.T. Wall’s in Old Town is perfect for a date-night dinner or a celebratory meal to cap off your tasting day. Visit Website
The Market at Kimberly’s
Kimberly’s is one of those places that instantly makes a trip feel more “local.” Browse the boutique, then stop into The Market at Kimberly’s for gourmet goodies, snacks, and easy treats you can take back to your hotel. Visit Website
Sunday brunch: Bonnie Blue Southern Market & Bakery
Before you head home, make Bonnie Blue your Sunday brunch stop. It’s a Winchester favorite known for its Southern comfort classics and baked goods, and it’s open Saturday and Sunday mornings—perfect for a final “one more great meal” before the drive. Visit Website
A simple weekend itinerary (Winchester + James Charles)
Friday evening
- Check in
- Dinner at T.T. Wall’s
- Walk Old Town after dinner
Saturday
- Browse Kimberly’s + snack stop at The Market
- Visit James Charles Winery & Vineyard for your tasting and bottle pick
Sunday
- Brunch at Bonnie Blue
- One last stroll through Old Town, then head home
