One of the hardest pieces of my RTW will be leaving behind a serious boyfriend and trying to make the long distance game work. But to help keep things light and make sure my getting ready to go is as enjoyable for him as it is for me, we finally sat down this weekend and distilled all our passing “We should do that sometime soon” comments from the past several months into a Charlottesville bucket list. It’s a mix of local must-dos, recently opened joints I have yet to hit, and a few special nights in. It’s going to be a busy five months!

Five Restaurants We Don’t Often Eat At:

Five Watering Holes for Drinks Both Alcoholic and Non:

Five Wineries:

Five Other Foodie Moments:

  • Cheese tasting at Timbercreek Market
  • Make fresh pasta
  • Have crepes at The Flat and browse the farmers market
  • Plant Jo’s backyard garden
  • Grab one last Bodo’s bagel

Five Day Trips:

  • Richmond for Lake Street Dive concert
  • Up 29 North to take my roommate to Bamboo House
  • Staunton for a play at Blackfriars
  • Scottsville for tubing on the James River
  • Batesville for cherry picking and pizza at Dr. Ho’s

Five Trails for Hiking:

  • Old Rag
  • Crabtree Falls
  • Blue Hole
  • Saunders-Monticello
  • Walnut Creek Park

Five Other Activities:

Looking for more fun things to do in Charlottesville? Check out these eight local treasures too many visitors miss.

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