Art Pop-Up
- Lynn Clark
- Jan 31
- 3 min read
Nestled in the heart of Downtown Winter Haven, Tree Swallow Gallery is a pop-up art destination dedicated to celebrating the unique spirit and creativity of Central Florida’s local artists. Curated by Amanda McCallister, the gallery focuses on hyper-local talent, showcasing carefully selected fine art that reflects the beauty, history, and culture of the Winter Haven community and its surrounding areas.
Tree Swallow Gallery embraces its pop-up nature, offering a dynamic experience with curated exhibitions, flexible hours tailored to downtown events and foot traffic, and unique opportunities to connect with both the art and the artists. From stunning landscapes and evocative photography to thought-provoking mixed media, the gallery provides a platform for authentic storytelling through art.
With its focus on community engagement and accessible artistry, Tree Swallow Gallery is more than just a space for viewing art—it’s a celebration of the people, places, and stories that make Polk County unique. Whether you’re a lifelong resident, a curious visitor, or an art enthusiast, Tree Swallow Gallery invites you to explore the heart of Florida through the lens of its most talented artists.

Level Up: Art Boss Academy
Level Up: Art Boss Academy is designed for student artists with ambitions and a drive to master the business side of art. This isn’t about creating art—it’s about building a future with art. Gain insider strategies and actionable insights, from growing your online empire to making a lasting impression in real-world spaces. This series is packed with hands-on guidance to help you stand out, connect with your audience, and start seeing real results. The series began in January and continues until March 1.
Slide Into Sales: SM Essentials February 1 from 2 pm to 3:30 pm
Bag the Merch: POD Basics February 22 from 2 pm to 3:30 pm
IRL Vibes: Gallery Cheat Codes March 1 from 2 pm to 3:30 pm
On Saturday We Make Art
More than just a series of art classes—it’s a creative movement. Rooted in fun, self-expression, and empowerment, this series is all about tapping into your artistic side in a space where they listen, they don’t judge. These sessions are a fearless exploration of creativity for people who are ready to create, connect, and let their imaginations run wild. Whether you’re snapping pics on your phone or diving into hands-on projects, every class is designed to inspire, uplift, and help you embrace your inner artist. Saturdays are for more than just making art— they’re for building confidence, friendships, and a creative community that celebrates your unique vibe. Come as you are and make something unforgettable.
Plein Air Sketching with Denise Settles--February 8 from 2 pm to 4 pm
Neurogenic Drawing with Sherry Ross--February 15 from 2 pm to 4 pm
Get Involved With Tree Swallow Gallery
Tree Swallow Gallery offers several ways to engage with our creative community:
•ATTEND EXHIBITIONS AND EVENTS: Visit the gallery during our curated exhibitions and special events to experience the incredible work of local artists and connect with the community.
• BECOME A FEATURED ARTIST: If you’re a local artist with work that reflects the spirit of Winter Haven and Central Florida, reach out to discuss opportunities to showcase your art in one of our upcoming pop-up exhibitions. Contact Amanda at amanda@mccallisterventuresllc.com
• VOLUNTEER: We’re always looking for passionate art lovers to help with events, installations, or day-today operations. Your support helps us bring art to life for our community. Contact Amanda at amanda@ mccallisterventuresllc.com
• FOLLOW US ONLINE: Stay updated on gallery events, operating hours, and artist features by following us on social media or subscribing to our newsletter.
• SPREAD THE WORD: Share the gallery with friends and family! Help us grow by inviting others to explore the art and stories that make Winter Haven unique.
Tree Swallow Gallery
337 W Central Ave, Winter Haven
FB & IG @treeswallowgallery
Tuesdays & Wednesdays 11 am - 2 pm
Thursdays & Fridays 5 pm - 8 pm
Saturdays 11 am - 8 pm
By special appointment, please call 863-225-0520
Photo by Amy Sexson