September 5, 2026
Winchester, VA
#witherallways
Things To Do
Paladin Downtown
31 East Piccadilly Street, Winchester, VA 22601
Our favorite spot to eat downtown! Enjoy a unique atmosphere just a short walk from the downtown walking mall.
Oak Stone Craft Pizza and Bar
1000 Valley Avenue, Winchester, VA 22601
Another favorite of ours! Their pizzas and cocktails are hands down the best in the area!
Museum of the Shenandoah Valley
901 Amherst Street, Winchester, VA 22601
Enjoy the free trails, gardens, or museum at this scenic location!
West Oaks Farm Market
4305 Middle Road, Winchester, VA 22602
A laid-back location offering a playground, corn maze, flower-picking, produce, and baked goods. Fun Fact: Our Rehearsal Dinner will be located at West Oaks!
James Charles Winery & Vineyard
4063 Middle Road, Winchester, VA 22602
A Winchester staple with delicious wine, food, and beautiful scenery! Fun Fact: Karli’s Bridal Shower was hosted here!
Kimberly's
135 North Braddock Street, Winchester, VA 22601
A local boutique in Winchester, you can find everything from Lilly Pulitzer to Simply Southern. Head right next door to The Market for wine, homemade ice cream, and gourmet food offerings.
For all the days along the way