Josephine & Jacob
Our Favorite Things
Shenandoah Apple Blossom Festival
The Shenandoah Apple Blossom Festival is a 10 day event that will be taking place from April 26th-May 5th! Swing by Old Town Winchester Friday night and experience the fun. With endless street food options you’ll be sure to find something delicious!
Old Town Winchester
Walking mall with different restaurants and bars. Check out our favorite sushi restaurant, Awabi! Or enjoy a glass of wine at The Wine Room! Street parking free on weekends. Parking garages within walking distance.
Awabi Sushi Bar
❤️🤤
Paladin Downtown
Newest Winchester find! The cheesesteak egg rolls are 🤌🏻 *chefs kiss*
Roma Old Town Wood Fired Pizzeria
Located in the walking mall of Old Town Winchester. Their mozzarella sticks are the bomb.com
Gringo Gordo Empanada Shop
Located in the walking mall of Old Town Winchester. You can’t go wrong with any of them. We highly recommend the Caprese, black bean & corn, and Argentine beef empanadas!
Chop Stick Cafe
Located close to Old Town Winchester
Duck Donuts
NC favorite has made its way to Winchester! 🍩
Bonnie Blue Southern Market & Bakery
Bloody Mary’s, breakfast beer, BBQ & pastries. Great for breakfast and lunch.
Waffle House
Is an explanation really necessary?
Los Toltecos Mexican Restaurant
Cheap and cheerful!
Packs Cones n More 522
Ice cream treat 🍦
James Charles Winery & Vineyard
James Charles has been one of our favorite wineries in Winchester since we moved here. Stop in for a tasting!
Veramar Vineyard
Veramar is the Italian sister of James Charles. She’s located about 20 minutes from Winchester and the view is absolutely worth it!
Winchester Brew Works
Enjoy some nice beers on tap while playing a fun round of foosball. Or sit on the patio and enjoy the beautiful view of Winchester’s Apple Blossoms!
Museum of the Shenandoah Valley
Great walking trail!
Strasburg Emporium LLC
You can spend hours here & will most definitely walk out with an antique! Located about 30 minutes South of Winchester.