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  • Lowest Rate Guaranteed
  • Breakfast included
  • Complimentary Wi-Fi
  • Free off-street Parking
  • Free EV/Tesla Charger
  • Smoke-free Rooms
  • Only children 14 years and older
  • No pets

Things to Do in Charlottesville in May

May is such an exciting month in Charlottesville! With ongoing events like Fridays After Five (a free weekly concert series downtown) and the Saturday morning City Market in full swing, there is so much to do each week. If you are visiting the area on Wednesday’s you my want to check out the Farmer’s in the Park.  To add to the previously mentioned events that will continue through the summer, May brings such unique and fun events to the area. Here are some of our favorites:

  1. First Wednesdays at King’s Family Vineyards: May 3rd. On the first Wednesday of each month, there are extended hours until 8:30pm at this lovely vineyard. Enjoy local food from Charlottesville’s great food trucks and music from a local band, Oh Wow Boy, with a view of the sun setting over the Blue Ridge Mountains. The food will be served from 5pm-8pm. Wednesday
  2. Montpelier Wine Festival: May 6th and 7th. This event looks fantastic, with the festival held on James Madison’s estate, Montpelier, in Orange, Virginia- just a short trip from Charlottesville. Virginia wineries, arts and crafts vendors, specialty food vendors, live music, carriage rides, and even more will all be featured! Saturday and Sunday
  3. IPA JamBEERee: May 6th. This festival, which takes place at Star Hill, a nearby local brewery, will feature 25 local, Virginia breweries with the focus on their IPA style beers. You can expect local food from some of the best Charlottesville food trucks, and great local music from bands like Camomile and Whiskey. Saturday
  4.  Crozet Arts & Crafts Festival: May 13th and 14th. Visit this award winning arts and crafts festival to see a juried art show, along with plenty of activities for all ages. From fantastic musical entertainment to delicious local food and wine to the abundance of arts and crafts tents set up for browsing and shopping, you cannot go wrong with this two day festival! Saturday and Sunday.
  5. Tuesday Tunes with the Onlies & Vivian Leva: May 23rd. James Monroe’s Highland is hosting this third annual edition of a six part outdoor concert series that features local musicians along with local food and alcohol venders. You can even bring your own picnic to enjoy while listening to a great concert! Tuesday
  6. Virginia Hot Glass Festival: May 27th and 28th. This interesting, artsy festival held at Sunspots Studios in Staunton, Virginia is completely free. You can shop for unique glass art pieces and jewelry, as well as see live demonstrations from local hot glass artists throughout the two day festival. Saturday and Sunday


Starr Hill Brewery                         Monroe’s Highlands                    Montpelier Garden


We hope to see you in May!

Dan & Kathryn

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