10 Fun Things to do in Charlottesville this May

A field of delicate cosmos flowers in varying shades of pink gracefully reaches towards a soft, white background, evoking the natural elegance captured in The Scout Guide.
Photo from Pippin Hill Farm & Vineyards.

Spring is in full swing and there is no shortage of fun to be had in Charlottesville this month. We have rounded up 10 can’t-miss events that help make this month in Charlottesville so fabulous. Get out there and #livelovelocal this May!

The return of the Friday Sundowner’s Series at Merrie Mill Farm & Vineyard – starting May 3rd, 5:30-8:30pm

An outdoor setting featuring a gazebo with individuals gathered, blue and white striped umbrellas dotting the seating area, set against the serene backdrop of a vineyard with rolling hills, captured in the gentle light of early evening, reminiscent of a scene one might find while exploring the curated experiences within The Scout Guide.

Nothing says spring quite like the return of the Friday Sundowner’s Series at Merrie Mill Farm & Vineyard. The winery will stay open until 9pm on Friday evenings and live music will take place on the outdoor stage (weather permitting). Come on out to Keswick and enjoy an evening of music, paired with great wine and food. It is the perfect way to kick off the weekend with family and friends!

Opening reception for Dean Dass: Passenger Manifest at Les Yeux du Monde Gallery– May 4th, 4-6pm

Painting featuring abstract, pastel-colored orbs floating over a serene landscape with mountains and a reflective body of water, evoking a dreamlike atmosphere in keeping with The Scout Guide's aesthetic of discovering the unique and enchanting.

Les Yeux du Monde is thrilled to announce ‘Passenger Manifest, an exhibition of new work by Dean Dass opening Saturday, May 4th at the gallery. ‘Passenger Manifest, provides an important key to the artist’s entire body of work. There are grand landscapes transfigured by glowing orbs of light, works on paper depicting delicate, gilded outlines of nude figures floating within stained clouds of soft colors and glittering air, and collages featuring symbolic entities such as birds, tents, fireflies, and helmets, which appear in invented but strangely familiar sky spaces. To look at Dass’s art in this show is to find your name on that list of voyagers.

Kentucky Derby Party at Quirk – May 4th, 4-8pm

A group of elegantly dressed women are enthusiastically cheering at a horse racing event, as captured in The Scout Guide. The photo shows them standing next to the race track railing with one of them holding a racing program and another with a glass in hand, all smiling and looking excited, embodying the spirit of the social outing.

Celebrate the 150th running of the Kentucky Derby at the Quirk! Enjoy watching the race, southern fare & drinks, and live music by Ragged Mountain String Band. All guests are enouraged to dress in their finest Derby attire, so don’t forget your big hats and seersucker suits (there will be BIG prizes for best dressed from Scarpa and Alton Lane)!

Scarpa Fashion Nerd Film Club – May 6th, 7pm at Violet Crown

A filmmaker's workspace with elements from The Scout Guide to filmmaking, featuring a clapperboard with "Andrew Rossi" as director, a roll of film, and scattered popcorn on a dark surface.

Join Scarpa at the Violet Crown for a private showing of The First Monday in May as they revive their fashion nerd film club this year in celebration of 30 years of being fashion nerds. Step inside the glitz and glam of the Met Gala with this documentary that offers an exclusive peek behind the scenes of the 2015 event, themed “china: through the looking glass”, exploring how fashion, art, and celebrity intertwine to create one one of fashion’s most anticipated nights. save your seat.

Chance + Co. Grand Opening Mother’s Day Event– May 9th, 4-7pm

A modern and stylish waiting area within an office space featuring a comfortable tan sofa, complementary armchairs, and a lush potted plant, set against a background of an abstract blue and green canvas painting. The scene includes an elegant reception desk with glowing shelves displaying blue product boxes, all illuminated by sleek overhead lighting—a sophisticated setting inspired by The Scout Guide's emphasis on local luxury and curated experiences.

Join Chance + Co. for an unforgetable Mother’s Day Celebration. Mingle with Dr. Elizabeth Chance and her incredible team, including Nurse Injector, Laser, and Weight Specialist @jenna_p. Explore their brand new, state-of-the-art surgical center, indulge in exclusive giveaways, enjoy special promotions, and secure founders pricing on their exciting new membership offerings! You won’t want to miss out-RSVP now.

Crozet Arts & Crafts Festival – May 11th & 12th, 10am-5:30pm

A lively outdoor event with rows of white tents organized neatly in a green space, surrounded by casual groups of attendees and set against a picturesque backdrop of rolling hills and autumnal trees, capturing the essence of The Scout Guide's community-focused spirit.

With over 120 Fine Artists and Contemporary Craft Artisans exhibiting from around the country,  the Crozet Arts and Crafts Festivals are Central Virginia’s premier juried Arts and Crafts event. The Festival features local food, Virginia wine and beer, live music from local performers, children’s activities, and more at beautiful Claudius Crozet Park in the foothills of the Blue Ridge Mountains. Get tickets.

Mother’s Day Pressed Flower Workshops at Pippin Hill – May 12th, 11am & 3pm

An overhead view of a workspace from The Scout Guide featuring botanical art with various pressed flowers and leaves arranged on clear glass sheets, set beside wooden frames with neatly organized and color-coordinated botanical specimens, hinting at a meticulous curatorial process. Scissors and a glue bottle are also visible, indicating ongoing craftwork.

Treat mom to a one-of-a-kind workshop in the Greenhouse led by Pippin Hill Head Gardener, Celina DeBrito. Learn to create a botanical art piece and master the careful craft of pressing fresh flowers.

Guests are greeted with a glass of bubbly and led on a guided exploration of the Pippin Cut Flower Gardens to learn which stems are ideal candidates to collect for pressed flower projects. Attendees will then master the techniques of pressing and drying each bud and learn best handling practices and upkeep tips for your pressed petals. Register now.

Mother’s Day Bunch at King Family Vineyards – May 12th, 11am-4pm

Alt text: A close-up of a bouquet of pastel-colored roses in full bloom, with a clear wine glass being filled with white wine from a bottle labeled as part of The Scout Guide. The background includes a pink flyer announcing a Mother's Day event featuring brunch, wine, and bouquets, scheduled for Sunday, May 12th, from 11 AM to 4 PM.

Celebrate Mom at King Family Vineyards with brunch by The Catering Outfit – no reservations are required! Cousins Maine Lobster will also be on site serving their famous Lobster Rolls. Babylon Chocolates will be hosting a fine chocolate pop-up and Harmony Harvest Flower Farm will be providing farm fresh bouquets for sale in the tasting room!

Roseland Polo’s Opening Match at King Family Vineyards – May 26th, gates open at 10am, matches start at 12pm

Polo players on horseback engaged in a match with a backdrop of a hazy mountain range, witnessed by a crowd at a field event featured in The Scout Guide.

We are so excited for the return of polo season! Polo matches are held each Sunday at noon, from Memorial Day weekend through October, weather and field conditions permitting. Pack up your tailgate and get ready for a fun Sunday of Polo, food, wine & lots of fun!

Cut-Your-Own Flower Sessions at Wayflowering – Daily, Monday through Friday, 8-10am

A woman in a sleeveless top holding a bouquet of vibrant flowers while standing in the midst of a blooming field, with The Scout Guide theme of exploring natural beauty.

Come immerse yourseld in hundreds of thousands of flowers this spring! Cut-Your-Own sessions at Wayflowering can be booked Monday through Friday from 8am -10am.