May in Charlottesville: Top Things to Do - Outdoor Adventures, Local Markets, Wineries

May is a fantastic time to visit Charlottesville and Albemarle County, as the weather starts to warm up and the region comes alive with a plethora of events and festivals. Whether you're a history buff, a nature lover, a foodie, or just looking for a fun weekend getaway, the Charlottesville area has something for everyone.

1. Go to a Community Festival

The Charlottesville-area community is vibrant and full of reasons to celebrate, and May is packed with can’t-miss festivals and events. Planning your trip around one of these standout happenings is a great way to make the most of your visit -- take a look and see what’s worth adding to your calendar.

2. Enjoy 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.

Credit: Skyclad Aerial

Every Friday

Fridays After Five

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 concerts feature various musical styles and include collaborations with a number of local organizations, celebrating the diverse and creative communities throughout Charlottesville. There is truly something for everyone!

Every Other Saturday

Rivanna Roots Concert Series

The Rivanna Roots Concert Series kicks off on May 2nd, 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.

Every Fourth Friday

Fridays on the Canal

Scottsville's free concert series, Fridays on the Canal, happens every fourth Friday of the month from May - September! There will be food trucks, local wine/beer, and local vendors. Their season kicks off on May 22nd with the Cody Purvis Band.

3. Get Outdoors

Spend a Day 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!

Go on a Sunset River Cruise

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 alcoholic/non-alcoholic beverages you bring!

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.

Go to the Farmers Market

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!

4. 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!

5. 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 eight 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!

6. 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.

Plan Your Stay

One day is never enough to experience everything Charlottesville & Albemarle County has to offer. Extend your adventure with an overnight stay and wake up ready to explore award-winning wineries, historic sites, mountain trails, local restaurants, and unique shops. Browse our Places to Stay page to find the perfect accommodations, then visit our Guides and Itineraries page for even more ways to build your ideal trip.

One blog couldn’t possibly capture everything that’s happening in Charlottesville and Albemarle County! Head over to our upcoming events page to stay up to date on all the latest happenings in the area.

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