1. Go to An Event/Festival
With a vibrant performing arts scene, there's always something fun to do for you and your family! Here are a few of our favorites!
2. Enjoy Some Live Music
You don't have to look far to find music in Charlottesville! We recommend checking out our calendar of events page to learn more about all the musical happenings in and around town during your visit -- just filter by date and category. You can also check out local venues like the Jefferson Theater, The Southern Café & Music Hall, the Ting Pavilion, and the Paramount Theater for upcoming concert dates.
Charlottesville's FREE concert series, 'Fridays After Five,' is held at the Ting Pavilion each week through September 5th. The full lineup can be found on their website. The summer schedule features local artists performing a wide range of musical styles and will see collaborations with a number of local organizations, celebrating the diverse and creative communities throughout Charlottesville; there is truly something for everyone!
The Rivanna Roots Concert Series kicks off on May 3rd, with 13 shows scheduled throughout the summer, every other Saturday. This dog- and family-friendly outdoor concert series takes place right alongside the banks of the Rivanna River! Concert-goers are highly encouraged to bring their own blankets, chairs, and reusable cups in an effort to reduce waste.
3. Get Out on the Water
With the arrival of warmer weather and the opening of our local outdoor outfitters for the season, May is the best time to kayak, go rafting, or try paddle boarding on the James or Rivanna Rivers.
More interested in admiring the water and staying dry? Journey out for an unforgettable evening with the James River Batteau Company. They offer sunset cruises on the James River every day of the week as well as special Farm to Batteau outings, which include live music, family-style dinner cooked over an open fire, and plenty of ice buckets and cups for any beverages you bring (alcohol is allowed!)
4. Find Your New Favorite Cycling Route
The Charlottesville area is a haven for cycling enthusiasts, with its picturesque countryside and scenic routes. Rent a bike or bring your own and explore the numerous trails along the Rivanna Trail System or Albemarle County Parks.
May is National Bike Month, with pleasant weather for outdoor activities making it an ideal time for a leisurely bike ride. Take part in local cycling events through Cville Bike Month or explore popular Trails & Outdoor Routes — including the beautiful Western Albemarle Scenic Tour.
The roads of the Western half of Albemarle County sit at the base of the Blue Ridge Mountains and are bordered by farms, orchards, wineries, and beautiful parks.
Learn More5. Go to the Farmers Markets
In late April/May, the Charlottesville City Market and Scottsville Farmers Market return for the season along with many others! Check out our farmers market page for a full list of markets and where/when you can find them! Remember that the Mobile Visitor Centers are on-site at the Farmers Market at IX Art Park each weekend to provide more information about the area and offer recommendations!
6. Pick Your Own Fruit
After spending some time at the markets, go pick your own strawberries at Chiles Peach Orchard in Crozet! It's a fun and wholesome activity for families or anyone who enjoys the taste of fresh strawberries. Pick juicy berries straight from the fields, enjoy fresh ice cream, and listen to the live music that Chiles so often has!
7. Celebrate BBQ and Hamburger Month
May is both BBQ and hamburger month, and with so many amazing restaurants in the area, indulging in Charlottesville and Albemarle County is the perfect way to spend the month! Here's our list of the top seven burger joints in the area -- we recommend grabbing a mouthwatering smashburger at Högwaller Brewing or building a custom burger at Citizen Burger Bar. For the best BBQ, head to Smoked Kitchen and Tap or Vision BBQ -- you can't go wrong!
8. Sip Award-Winning Wine
May is a great time to explore Charlottesville & Albemarle County's wine scene - recently named Wine Region of the Year by Wine Enthusiast! Make a plan to visit the 40+ wineries along the Monticello Wine Trail where you can sip everything from chilled wines to bold reds to exciting hybrids. Many of our area wineries are nestled against the stunning backdrop of the Blue Ridge Mountains, offering you a quiet, scenic getaway with world-class wine.
Down to Earth Destination, World Class Wines
Welcome to the birthplace of American wine. Charlottesville and Albemarle County are home to more than 40 wineries along the Monticello Wine Trail, offering visitors lush views and a dynamic wine scene in the heart of Virginia.
Learn MorePlan Your Stay
Take in all that May has to offer in Charlottesville and Albemarle County by staying a while! Mid-week stays will reward you with lower rates and more availability during this popular spring travel season. Check out the places to stay page below for a variety of options.