Cuppa Giddy Up
Dog rule: Listed as dog-friendly on BringFido. Cuppa Giddy Up is a coffeehouse with pet-friendly outdoor seating in downtown Middleburg, VA. Bring Fido along while you enjoy caffeine and light eats on the cobblestone sidewalk of charming Washington Street. They serve cold &, hot coffee, tea, bagels, and pastries.
Unconfirmed: Third-party only Checked Nov 10, 2026. Source
