Ginny's Guidebook
Food Scene
Great coffee, great atmosphere, and also a record store!
18 locals recommend
Hopscotch Coffee & Records
250 Millwood AveGreat coffee, great atmosphere, and also a record store!
Taste Winchester History
149 N Loudoun StAMAZING food!
Great atmosphere, live music, great food and drinks. Always lively on the weekends. Trivia Nights.
27 locals recommend
Piccadilly's Public House & Restaurant
125 East Piccadilly StreetGreat atmosphere, live music, great food and drinks. Always lively on the weekends. Trivia Nights.
A new kind of farmers market! Has a cafe with a large menu. Everything made fresh. Great for days with the family. Has a playground for kids,corhole, corn maze, pumpkin patch, indoor kids area and large selection of locally grown produce!
10 locals recommend
West Oaks Farm Market South and Event Center
4305 Middle RoadA new kind of farmers market! Has a cafe with a large menu. Everything made fresh. Great for days with the family. Has a playground for kids,corhole, corn maze, pumpkin patch, indoor kids area and large selection of locally grown produce!
Delicious pizza, house made sangria, a brewery upstairs. This place has it all!
14 locals recommend
Roma Old Town Wood Fired Pizzeria
21 N Loudoun StDelicious pizza, house made sangria, a brewery upstairs. This place has it all!
Sightseeing
Skyline Drive
Skyline DriveBeautiful views! You can drive or hike to the top
Beautiful views, just a short drive away! You can do a <1 mile hike to the top, or drive to the top and take in the gorgeous scenery.
69 locals recommend
Bears Den
18393 Blue Ridge Mountain RdBeautiful views, just a short drive away! You can do a <1 mile hike to the top, or drive to the top and take in the gorgeous scenery.
Breweries + Wineries
Beautiful scenery, amazing staff, great cider! Its dog friendly. They have live music and food trucks on the weekends.
17 locals recommend
Winchester Ciderworks
2504 N Frederick PikeBeautiful scenery, amazing staff, great cider! Its dog friendly. They have live music and food trucks on the weekends.
Dirt Farm Brewing
18701 Foggy Bottom RdGreat beer, beautiful views, and dog friendly!
Amazing wine in a beautiful historic house with beautiful country views!
26 locals recommend
Valerie Hill Vineyard & Winery
1687 Marlboro RdAmazing wine in a beautiful historic house with beautiful country views!
Great wine and great views! Try their mulled wine in the late fall/winter!
25 locals recommend
James Charles Winery & Vineyard
4063 Middle RdGreat wine and great views! Try their mulled wine in the late fall/winter!
Gorgeous views and great beer. Sits on top of a mountain right by Bears Den Trail.
97 locals recommend
Bear Chase Brewing Company
33665 Bear Chase LnGorgeous views and great beer. Sits on top of a mountain right by Bears Den Trail.
Our Favorite Breafast Places
Freshly made donuts each morning! Go early or you'll have slim pickings!
They also have gluten free donuts on Saturdays!
Moe's Donut Shop
28 E Piccadilly StFreshly made donuts each morning! Go early or you'll have slim pickings!
They also have gluten free donuts on Saturdays!
Freshly made in-house biscuts, local fried apples, and some of the best BBQ ever!
28 locals recommend
Bonnie Blue Southern Market & Bakery
334 W Boscawen StFreshly made in-house biscuts, local fried apples, and some of the best BBQ ever!