Whether you have a free evening or are looking for an excuse to leave the house, there is plenty in store at Downtown Cary! Check out what’s in store for May, 2025:
School BreakOUT!
May 2 @ 10:00 am – 4:00 pm – Downtown Cary Park
Join us at the Park for School BreakOUT! This free, family-friendly day is the perfect way to enjoy time together when school’s out. Explore creative fun at the Art Cart, play your way through the Park with various lawn games, and enjoy a relaxing day of open-ended activities. It’s all about low-key fun, fresh air, and making memories— just play at your own pace!
For more information: https://downtowncarypark.com/things-to-do/calendar/w_school-breakout-7
Cary Players Presents Sonia Flew
May 2-4 and May 9-11 @ 7:30 pm – 9:30 pm (Sundays @ 3:00 pm) – Cary Arts Center
When Sonia learns of her son’s decision to leave college, enlist in the military and fight against terror in Afghanistan in the weeks following 9/11, memories of her own childhood overwhelm her. She struggles to reconcile being forced as a young girl to leave Cuba at the dawn of Fidel Castro’s rule with her own responsibilities as a mother facing uncertainty. Sonia must find a way to come to terms with her past, her lost parents, her own children and her adopted country—or risk losing everything that she loves.
For tickets: https://www.caryplayers.org/
Cary Farmers Market
May 3, 10, 17, 24, and 31 @ 8:00 am – 12:00 pm – East Park St
Join the Cary Farmers Market for the traditional market season along East Park St., next to Downtown Cary Park.
Find a wonderful lineup of vendors offering all locally made and locally grown items. Shop for freshly-harvested produce, humanely-raised meat, and artisan-made goods. Stop by the info booth to learn about their matching program for SNAP/EBT.
Children can also get their very own Farmers Market Passport and participate in the Eat-A-Rainbow program, which encourages children to eat healthy, nutritious foods. Learn more about the new location, nutrition programs, and other information on their website or their Facebook and Instagram pages for regularly updated weekly information.
Cary Dog Daze and Pet Expo
May 3 @ 10:00 am – 3:00 pm – Cary Police Department 120 Wilkinson Ave., Cary
-Need a groomer, trainer, doggie day care, boarding, vet, or some really cool pet stuff?
-Want to support some amazing rescue groups and see some adoptable animals?
-Like, boba teas, cold brew coffee, empanadas, american foods, cotton candy and popsicles?
-Want to hang out with a bunch of people who love animals as much as you do?
Then we will see you on the Town Hall campus on May the 3rd!!
Home is Distant Shores Film Festival 2025
May 3 @ 12:00 pm – 5:30 pm – The Cary Theater
Home Is Distant Shores Film Festival is a celebration of resilience, grit, and the unbreakable spirit of immigrants and refugees. These are not just stories of struggle but of triumph—of individuals who rise above hardship, shape new identities, and redefine what it means to belong. Through powerful films, we honor the relentless drive of those who have left everything behind to build a future against the odds. Witness their journeys, their courage, and their unstoppable pursuit of dreams—because the immigrant story is not one of survival alone, but of victory.
Film Block 1: Abrazo, Desi Mom, How Much Filipino, Little Birds, “Me, Dad, Niu-York”, Nyasha, Pari and the witch, Red Rice and Under One Sky.
Film Block 2: Ayat (Verses), Bogotá Story, Children of diaspora, Frozen Out, “Here, Hopefully”, Love in the Time of Migration, Plastico and Rice & Grits : A Vietnamese American Culinary Odyssey of the American South
May the Fourth Be With You
May 4 @ 1:00 pm – 5:00 pm – Downtown Cary Park
It’s time to choose your side. Will you “Embrace the Dark Side” or “Join the Resistance” at our May the Fourth Star Wars celebration? Grab your best Star Wars gear and costumes and join us in the Park for a celebration of a galaxy far, far away.
Celebrate Star Wars at Downtown Cary Park with a galaxy of themed activities for fans of all ages! Join Playwell TEKnologies’ LEGO builds where you’ll help our Ewok friends rebuild their treehouses on Endor and construct speeder bikes to chase down Imperial droids. Test your skills in Jedi Training—free lightsabers will be handed out while supplies last! Enjoy Star Wars trivia with Hammered Trivia, a ChewBARKa dog costume contest with prizes (sign your pup up here to participate), and roaming 501st Legion cosplayers bringing the galaxy to life.
Don’t miss the Kyber Crystal scavenger hunt, Endor scene terrarium building with Garden & Gather, Yoda-inspired poetry writing with Chris Vitiello, and a 360° photo booth experience. Plus, check out the Galactic Showcase, where Park guests can display their own LEGO creations from home during the event!
| TIME | PROGRAM/ACTIVITY | LOCATION |
| 1 – 4 p.m. | Yoda Wisdom Tanka Poems with Chris Vitiello | Gathering Garden |
| 1 – 5 p.m. | Art Cart- R2D2’s Droid Design | Nest Pavilion |
| 1 – 5 p.m. | Playwell Teknologies Lego Star Wars Creations | Academy Pavilion |
| 1 – 5 p.m. | Galactic Showcase – Learn more and submit your lego design here! | Academy Pavilion |
| 1 – 5 p.m. | Endor Scene Terrarium Building with Garden & Gather | Academy Pavilion |
| 1 – 5 p.m. | Kyber Crystal Scavenger Hunt | Starts on Willow Isle |
| 1 – 5 p.m. | ZimZoom 360 Hyperdrive Photo Booth | Great Lawn Pavilion |
| 1 – 5 p.m. | Food Trucks: Trash Talk and MunchiLove | Park Street Courts |
| 1 – 5 p.m. | Roaming Photo Ops with Star Wars Cosplayers including the 501st Legion | Parkwide |
| 2 – 2:45 p.m. | Jedi Training Workshop (Grab a free lightsaber before the workshop—available while supplies last!) | Great Lawn Pavilion |
| 2 – 3 p.m. | Choose the BARK Side-Star Wars Trivia with Hammered Trivia (Session #1) | Bark Bar |
| 3 – 4 p.m. | ChewBARKa’s Runway-Dog Costume Contest (Prizes by Mosa Pet Spa and Resort)- REGISTER HERE | Park Street Arena |
| 4 – 4:45 p.m. | Jedi Training Workshop (Grab a free lightsaber before the workshop—available while supplies last!) | Great Lawn Pavilion |
| 4 – 5 p.m. | Choose the BARK Side-Star Wars Trivia with Hammered Trivia (Session #2) | Bark Bar |
For more information: https://downtowncarypark.com/things-to-do/calendar/w_may-the-4th-be-with-you-2
Live at Lunch with Story Charlemagne
May 8 @ 11:30 am – 1:30 pm – Downtown Cary Park
Spend lunch at Downtown Cary Park enjoying live local music.
This concert features Story Charlemagne on Academy Plaza. Story Charlemagne is a lover of stories shared through music. His soulful voice, progressive rock and indie sound leaves you guessing where the song and story will lead.
Grab lunch from Market 317, bring your own from home or any of Cary’s great downtown dining options.
For more information; https://downtowncarypark.com/things-to-do/calendar/w_live-at-lunch-9
Trivia Night at The Bark Bar
May 8 & 22 @ 6:00 pm – 8:00 pm – Downtown Cary Park
Get ready to test your knowledge and unleash your competitive spirit at Trivia Night in Downtown Cary Park’s Bark Bar! Led by the witty hosts from Hammered Trivia, it’s an evening packed with brain-teasing questions, laughter, and prizes. Gather your friends, grab a drink, and let the games begin!
For more information: https://downtowncarypark.com/calendar
Live Music: The Wilder Flower
May 8 @ 7:30 pm – 9:00 pm – The Cary Theater
The Wilderflower transitions effortlessly between folk, Americana, bluegrass, and Old-time melodies. With three-part harmonies leading the way, Danielle Yother on guitar, Madeline Dierauf on fiddle, and Molly Johnson on banjo, this group performed at IBMA in Raleigh and is now on tour promoting their debut album, “If I Wait Anymore”. This show, suitable for all ages, features amazing harmony and impressive fiddle/banjo/guitar performances that are some of the best in recent memory.
Watch: Youtube video
Listen: Spotify
Ritmo Latino Festival
May 10 @ 10:00 am – 6:00 pm – Town Hall Campus
Ritmo Latino Festival, presented by Diamante Arts & Cultural Center, is a fantastic annual celebration of Latino culture in Downtown Cary, North Carolina. It showcases the very best of Latino music, dance, and arts and is suitable for the whole family. The festival includes live music, food vendors selling delicious Latino cuisine, raffles and games, and even dance lessons for adults. The KidZone at Ritmo Latino Festival is full of entertainment for the kids, with cotton candy, inflatable rides, games, and plenty of activities to keep them busy.
The Cary Vintage Market
May 10 @ 12:00 pm – 5:00 pm – West End Biergarten
The Cary Vintage Market is a monthly vintage market held at the biergarten space between Vicious Fishes Brewery (Cary) and South Line Brewing. Located on the edge of downtown , this market is the only vintage market in Cary, NC. Here, you can expect to find a highly curated and diverse collection of:
•Vintage women’s and mens clothing
•Vintage shoes and accessories
•Vintage records, CDs and cassettes
•Vintage houseware and decor
•Vintage tchotchkes, memorabilia and collectibles
Plus:
•Permanent jewelry
•Craft coffee cart (NEW!)
•Specialty baked goods
•Craft beer, liquor drinks, wine and slushies
•Food trucks
Mother’s Day: Music & Pampering in the Park
May 11 @ 10:00 am – 3:00 pm – Downtown Cary Park
Celebrate Mother’s Day in the Park with a delightful afternoon of music, relaxation, and fun! Enjoy live performances by talented musicians from the North Carolina Chamber Music Institute, featuring the Adolpha Piano Quartet and Tailleferre Piano Quartet. Treat mom to a free chair massage, explore creative crafts at the Art Cart, and savor delicious bites from a local food truck. Join us for this special celebration honoring all the amazing moms!
While this program will not offer childcare, there will be a few activities inside the Academy Pavilion to entertain the kiddos within mom’s eyesight, allowing her to enjoy her free chair massage.
- 10 a.m. – 3 p.m.: Art Cart on the Academy Plaza
- 11 a.m. – 2 p.m.: The NOW Massage, Downtown Cary (free 15 minute chair massages) in Academy Pavilion
- 11 a.m. – 2 p.m.: Umbrella Dry Bar Mocktails on Academy Plaza
- 12 – 12:45 p.m.: Performance by the Tailleferre Piano Quartet on Academy Plaza
- 1 – 1:45 p.m.: Performance by the Adolpha Piano Quartet on Academy Plaza
Know Before You Go
- This is NOT a drop off event. Parents and guardians must stay with their child the entire time.
- This event is open to the public.
- This event is suitable for all ages.
Drop-in Puzzling and Puzzle Swap Meet
May 12 @ 10:00 am – 5:00 pm – Downtown Cary Park
Find the missing piece of your day at our drop-in puzzle program featuring a lively swap meet. Bring your favorite puzzles, trade with fellow enthusiasts, and enjoy a casual day of collaborative problem-solving and camaraderie. It’s the perfect opportunity to discover new challenges, share your passion for puzzles, and connect with like-minded individuals in a fun and relaxed family friendly setting.
Know Before You Go
- This is a drop-in program.
- All swap-meet puzzles should be in good condition with ALL pieces contained in their box.
- Puzzles will be exchanged for free, but in order to take a puzzle home, please bring a puzzle to share!
- This program is suitable for all ages.
The Really Terrible Orchestra of the Triangle (RTOOT) Presents: Pleasant Weather – Terrible Tunes
May 14 & 21 @ 7:30 pm – 9:00 pm – Cary Arts Center
The Really Terrible Orchestra of the Triangle (RTOOT) celebrates. Please join us for a delightful evening of music and unexpected humor. Concerts will be performed at the Cary Arts Center. Doors open at 700pm and the concert begins at 730pm.
For tickets: https://rtoot.org/concert-tickets/
Cary Night Market
May 16 @ 5:00 pm – 9:00 pm – Downtown Cary Park
Discover a vibrant showcase of locally-crafted treasures while immersing yourself in an evening of music and entertainment at the Cary Night Market, organized by The Night Market Co. Join Triangle area artisans for a monthly gathering where an eclectic array of goods meets delectable food and drinks!
Cary Town Band presents: Women Who Create Music
May 16 @ 7:30 pm – 9:00 pm – Cary Arts Center
For centuries, women have inspired music—but they have also shaped it as composers, pushing creative boundaries in every genre. From symphonies and opera to film scores and electronic music, their impact continues to grow. The Cary Town Band is proud to present a program highlighting the works of both historical and contemporary women composers, celebrating their artistry, innovation, and lasting influence. Join us in honoring their remarkable contributions to the world of music!
For more information: https://carytownband.org/
Verse-Chorus: A Songwriting Workshop
May 17 & 18 @ 10:00 am – 1:00 pm – Suite 230, 2nd Floor, The Cary Theater
Two-day workshop, one ticket includes both days
Ever wondered what goes into a song and how to get a song started? Are you currently working on your songwriting but feeling stuck or need some tools to keep you going? Kamara Thomas can help. Kamara is a songwriter with over 20 years of experience writing songs and working in a variety of settings, from bands to solo singer-songwriter to musical theater. She has been a teaching artist leading songwriting workshops for many years, and we are excited she is sharing her talents with us. Over the course of this two-day workshop, participants will learn Kamara’s tools and practices for:
- sparking creativity
- finding your specific viewpoint
- translating ideas, thoughts and feelings into compelling songwork
- finding your song’s structure
- building interesting melodies
- training your ear to listen for the “ideas” within songs for inspiration
All experience levels are welcome. No instrument necessary but bring one if you like!
Instructor: Kamara Thomas + guest artist
Wheels on Academy
May 17 @ 10:00 am – 2:00 pm – Town Hall Campus
Get ready to roll into fun at Wheels on Academy! This annual event in Downtown Cary is a celebration of all things wheels—from classic cars to modern marvels. Stroll through a dazzling car show, enjoy interactive exhibits, and explore hands-on activities for all ages. Whether you’re a car enthusiast or just looking for a great day out, Wheels on Academy has something for everyone. Don’t miss this exciting community tradition!
Triangle Youth Jazz Band and Triangle Youth Jazz Ensemble
May 17 @ 4:00 pm & 8:00 pm – Cary Arts Center
Join us on May 17th to see the Triangle Youth Jazz Orchestra and Triangle Youth Jazz Lab in concert!
CaryLIVE!: Flowmingos
May 17 @ 7:30 pm – 9:30 pm
Elevate your evening with the vibrant rhythm of CaryLive! Join us at Downtown Cary Park for another free CaryLive! musical experience featuring, Flowmingos. Opener is Shenette Swann. Enjoy the rhythms and bask in the beauty of the Park and music under the stars.
Upcoming Lineup
- June 28 – Dustbowl Revival
- August 23 – Squirrel Nut Zippers
- October 18 – TAE & The Neighborly
Know Before You Go
- This event is free and open to the public.
- Bring your own chairs and blankets for a comfortable viewing experience during the performance.
- This event is suitable for all ages.
Comedy Show: Tony Deyo with Paul Snyder
May 17 @ 8:00 pm – 10:00 pm – The Cary Theater
HEADLINER: Tony Deyo Bio
Tony Deyo is a stand-up comedian known most notably for his sharp, quick material and near-perfect comedic timing almost certainly gained from his years as a professional symphony musician. New York City’s Village Voice calls him “one of the tightest joke writers in the business.” In 2013, he made his late-night television debut on CONAN. Within a year, he had added appearances on The Late Late Show with Craig Ferguson, AXS TV’s Gotham Comedy Live, and Comics Unleashed with Byron Allen. His album, “Comedy Road Trip”, landed on the Billboard Magazine comedy chart and debuted as the #1 selling stand-up album on iTunes. He recently appeared on Jeff Foxworthy’s podcast, “A Comic Mind”, was named one of the year’s best by the New York Post, and can be heard regularly on SiriusXM Satellite Radio.
FEATURE: Paul Snyder Bio
Paul Snyder is a feature comic who performs his own unique brand of humor in clubs and theaters across the country. He was a finalist in the 2020 Jeanne Robertson Humor Competition, and will be filming his first DryBar special at the end of September. He’s a lovable introvert that has featured for Henry Cho, Michael Palascak, Aaron Weber, Brian Bates, and many others.
Ivey-Ellington House Ribbon Cutting and Open House
May 18 @ 1:30 pm – 4:00 pm – 308 S. Academy St.
After a two-year restoration, the Ivey-Ellington House is celebrating new life. A ribbon cutting and open house event will be held for this rare Wake County example of Gothic Revival cottage architecture on May 18 from 1:30 – 4 p.m.
Live at Lunch: Jared Place
May 22 @ 11:30 am – 1:30 pm – Downtown Cary Park
Spend lunch at Downtown Cary Park enjoying live musical performances as the melodious backdrop for the break in your day.
Live music will be performed by Jared Place on Academy Plaza. Jared Place writes simple songs about complex things: life, family, love, home, heaven. Since moving to Raleigh, NC in 2011, Jared has gained a powerful, word-of-mouth following. Often performing solo, Jared makes it look easy; his singing soul-soothing and his ‘feet on the ground’ optimism nothing short of healing.
Grab lunch from Market 317, bring your own from home or any of Cary’s great downtown dining options.
Know Before You Go
- This event is free and open to the public.
- Guests can bring their own food into the Park.
Live Music: Jared Benjamin
May 22 @ 7:30 pm – 9:00 pm – The Cary Theater
Jared Benjamin is back! After opening for The Nicotine Dolls at Downtown Cary Park, Jared brings his moody, caffeine-driven songwriting to the stage at The Cary Theater. Jared’s viral success with his first single, “Superhero”, has led to his decision to pursue music full time. Jared’s fan base on social media and streaming platforms has grown exponentially with over 1 million monthly listeners on Spotify and Apple Music, and over 1 million social media followers in total. Jared continues to release hits such as “Flatline”, “Doomsday”, “I’m the Sinner” and “Let it Burn.” Listen online and come sing along.
Watch: Youtube video
Listen: Spotify
Movie Night: Moana 2
May 23 @ 4:00 pm – 10:00 pm – Downtown Cary Park
In honor of Asian / Pacific American Heritage Month, join us for Moana 2 (PG), curated by The Cary Theater.
Set three years after her initial adventure, Moana embarks on a daring voyage to the far seas of Oceania, responding to an unexpected call from her wayfinding ancestors. Joined by a diverse crew from Motunui, including the demigod Maui, she seeks to locate the legendary island of Motufetu and confront the storm god Nalo to break a curse threatening her people. Throughout this perilous journey, Moana deepens her connection to her heritage, embraces her evolving identity, and discovers newfound strengths within herself.
Come early to enjoy pre-screening activities for all ages, making it a perfect night out for everyone. Activities will include arts and crafts in Academy Pavilion, a visit from Moana herself with a sing-along session on the Great Lawn, and swim safety tips and giveaways from Goldfish Swim School of Cary. Prescreening activities are from 6 – 8 p.m. The film will begin at sunset, approximately 8:20 p.m.
Grab your cushions, blankets, and chairs for ultimate comfort as you settle in to enjoy the film. Food trucks will also be on site.
Upcoming Lineup
- June 13 – The Lion King
- July 3 – Top Gun
- July 11 – Shrek
- August 8 – Guardians of the Galaxy
- August 20 – Wicked
- September 5 – Inside Out 2
- October 10 – The Nightmare Before Christmas
- October 25 – Double Feature: Hotel Transylvania & 1408
- November 7 – Big Hero 6
Know Before You Go
- This event is free and open to the public.
- Bring your own chairs and blankets for a comfortable viewing experience during the movie.
Big Top Circus Band
May 24 @ 7:00 pm – 8:30 pm – Downtown Cary Park
Step right up and experience the magic of the circus through music! The Big Top Circus Band will transport you back in time with lively marches, “screamers,” “cage cleaners,” and other classic circus tunes from over 100 years ago—rarely heard today! From 1900-1950, these thrilling melodies were traditionally played by a 20-piece circus band, either rolling through town on a parade bandwagon or setting the stage from above the Big Top entrance. Get ready for a nostalgic, toe-tapping journey into the golden age of the circus!
Know Before You Go
- This event is free and open to the public.
- This event is suitable for all ages.
Board Game Social
May 29 @ 4:00 pm – 8:00 pm – Downtown Cary Park
Enjoy Board Games in the Park, where you can gather with friends and family for an evening of delightful competition and fun. Indulge in the fantastic food and beverage offerings from Market 317. With tables, chairs, and games provided, this family-friendly space is the perfect setting to roll the dice, strategize, and enjoy a memorable night of tabletop gaming camaraderie.
Know Before You Go
- This is a drop-in program.
- This program is suitable for all ages.
Infinity Ballet Presents
May 31 @ 3:00 pm – 4:30 pm
Steadfast Songs of Friendship presents a fun-loving portrait of sisterhood as our performers trace the arc of developing relationships. The dancers leap, waltz, swirl and tap through a glittering stage performance. As part of Infinity Ballet’s twenty third anniversary celebration, the dance selections incorporation works of Ballet Classics to Musical Theatre.
For Tickets: https://www.etix.com/ticket/p/46548341/infinity-ballet-theatres-steadfast-songs-of-friendship-cary-cary-arts-center
Stay tuned for the excitement in store for June, 2025!