Charlottesville Spring Bucket List

Aerial shot of Chiles Peach Orchard Blooms by @aerowingva

Spring is almost here and we are looking forward to sunshine, warmer temperatures and longer days! To celebrate one of our favorite seasons in Charlottesville, we’ve created a Scouted Spring Bucket List filled with can’t miss events, places, and experiences recommended by our TSG Charlottesville members. Make the most of this beautiful season in Charlottesville by checking as many items off the list as possible!

#1 Visit the Quirk Rooftop for a Drink With Friends

Hannah Bell from Quirk Hotel loves enjoying sunset mountain views with a cocktail on Quirk’s rooftop. The rooftop is the perfect place to relax with friends and celebrate spring. It offers playful cocktails and rustic thin-crust pizzas in addition to its incredible views of the mountains.

While you’re there, don’t forget to stop by the Quirk gallery to see some beautiful art installations! Don’t miss the opening of Kiki Slaughter’s latest exhibition on Friday, April 5th from 5-8pm. Twenty Years marks the 20th anniversary of Kiki’s first solo show in 2004, held just across the street from Quirk Hotel at the original Main Street Market. This exhibition is a full-circle moment in her artistic career, celebrating two decades dedicated to the art of painting.

#2 Pick your own tulips at the Wayflowering Tulip Fest!

Christine Mahoney and the team of gardeners at Wayflowering planted 5000 tulips for you! Come cut-your-own bouquet of tulips and stroll among the first blooms of the season on Friday, March 29th and Saturday, March 30th. 50% of profits go to Cville Tulips a local nonprofit supporting Afghan refugee women and girls. Buy your tickets now.

Thistlerock Mead Co. will be pouring tastings of their delicious mead. Stay tuned for news of their grand opening coming this spring!

#3 Take a Trip to the Downtown Mall for Dinner & Live Music

The Downtown Mall is a popular spot among our members due to its great restaurants and live music scene, making it a can’t-miss spot this spring! Blair Williamson of Magpie Knits says: “The Magpies love spring because it gives us a good reason to get outside and enjoy dining al fresco on the downtown mall! Great people watching and adult beverages … and knitting, of course!”

Be sure to check out the spring lineup at Ting Pavilion. The 36th season of Fridays After Five kicks off on April 12th. Plan to join your friends and see the best of local talent all for free at the Ting Pavilion on the Downtown Mall.

While downtown, make sure you check out Tilman’s! Hannah Fleming of Easton Porter Group says: “My favorite thing to do in the Spring is to enjoy Tillman’s outdoor patio with a chilled glass of wine and charcuterie! It’s the best feeling after a long week of work. I love Tillman’s because there are many snack and lunch options in addition to their impressive wall of wine and food-inspired retail.” 

Kristina Loftus of Rhoback says: “I love getting a table outside at Mas Tapas and ordering sangria and a few small plates to share with friends  – it’s really hard to beat tapas, sangria and being outside in Belmont with friends on a warm day!”

#4 Go for a Drive to See the Spring Blooms

Charlottesville shines in the spring, and a drive on a sunny day is the perfect way to soak up the beauty of the season. Olivia Branch of Keswick Hall says: “I love a slow drive on 250 W near the YMCA when all the azaleas and dogwoods are in bloom. It becomes one of the most beautiful corridors in town if you take the time to look.”

Jill Grant of Gillian Valentine says: “I love driving down Route 231 from  Keswick to Gordonsville in the late afternoon enjoying the blooming trees as the sun sets.” Be sure to allow enough time to stop at the many fabulous wineries, breweries and cideries along Route 231.

#5 Enjoy Charlottesville Wine Country

King Family Vineyards says: “Wine Wednesdays at King Family Vineyards are a favorite spring activity of mine – especially the first Wednesday of the month when we have live music. It’s a great mid-week break to enjoy with the whole family. Spread out on the lawn, play games, enjoy a food truck and catch polo practice on the big, grass field. We stay open late (until 8:30pm) and when the weather is just right, you catch an amazing sunset!”

Spring is one of our favorite times to enjoy Charlottesville wine country. And with Charlottesville having been named the 2023 Wine Region of the Year by Wine Enthusiast, we feel especially grateful to have so many wonderful wineries right in our own back yard. In addition to Wine Wednesdays at King Family Vineyards we look forward to the following

Friday Sundowners at Merrie Mill Farm & Vineyard starting on May 3rd with live music from 5-9pm.

Live Music on the Hill at Pippin Hill Farm & Vineyards every Sunday from 12 -3pm.

Live Music at Southwest Mountains Vineyards most Saturdays and Sundays from 1-4pm.

Enjoying a chilled glass of wine from the mountain-view cabana at Knight’s Gambit Vineyard.

Enjoy the seasonal spring menu along with award winning wines at Early Mountain.

Mark your calendars for the Daze of Rosé Festival at Castle Hill Cider on Saturday, March 30th from 1-6pm. This annual celebration of Virginia Rosé promotes inclusivity and art by gathering wine lovers together in a beautiful location.  Drink pink, wear pink and celebrate spring in Virginia!

Keswick Hall Horizon Pool and golf course

#6 Enjoy a Staycation at Keswick Hall

Relax at the stunning Horizon Pool, play 18-holes on the award-winning Pete Dye Full Cry course, relax with a hand-crafted cocktail or partake in a game of petanque before sitting down to enjoy an incredible meal in the casually elegant ambiance of Chef Jean-Georges Vongerichten’s Marigold restaurant. Then settle into luxury accommodations for the night and let the vistas of the surrounding Blue Ridge Mountains greet you in the morning. Keswick Hall is a true get-away-from-it-all retreat just minutes from downtown Charlottesville, perfect for a little spring staycation!

#7 Spend Time Outdoors and Soak Up the Sun

Charlottesville spring is a season unlike any other, and it’s the perfect time to get outdoors and enjoy the sunshine and fresh air. Pnina Jalon of Studio Broad Design says: “One of my favorite things about spring in Charlottesville is trail running, and seeing and smelling all of the new life of fauna and wildflowers, sounds of happy chirpy birds with plenty to eat, creating an oasis easily escaped to.”

Molly Flora of Keswick Hall says: “My favorite spring activity in Charlottesville is hiking the trails at Monticello. The trees are bright green with new leaves, the sun is shining, the flowers are starting to bloom, and the birds are busy nesting.”

#8 Go to the Tom Tom Festival

During the spring, Charlottesville becomes a hub of exciting community events, and our members love the Tom Tom Festival! Rhoda Wheeler of Agents in Style says: “My favorite Spring event is the Tom Tom Festival, where the city gets together for a few days to support new businesses, meet new people, and dance in the Downtown streets!”  This year’s theme is Together and the festival runs from April 17-21.

#9 Goat Snuggling at Caromont Farm

Brooke Fossett of the Brow House says: “Goat snuggling at Caromont Farm! My family is obsessed and we look forward to those little baby goats every year!” While you’re there, make sure you check out Caromont’s selection of artisan cheese.

#10 Spring Equestrian Events

Nothing says that Spring has arrived in Charlottesville quite like the Spring Foxfield races. Foxfield has been hosting nationally recognized steeplechase races in Charlottesville for over forty years, giving both residents and visitors the opportunity to watch spectacular horse racing in the beautiful Virginia countryside. Don’t miss the spring races on April 27th.

Spring is also Hunter Pace season. This activity is sure to be a hit this spring, especially for those who are equestrians. George Payne of A.N Culbertson & Company loves hunter paces during the spring. Check out the Keswick Hunt Club and enjoy 5-7 miles on gorgeous property near the Rivanna River complete with fun jumps and other obstacles.

Enjoy spring & #livelovelocal in Charlottesville! Be sure to tell them The Scout Guide sent you!