It’s summer and you want to enjoy an evening out. Sure, the cineplex has air conditioning, but you’re in the mood for something a bit different. Something more enriching, engaging and exciting. Refreshments, of course, couldn’t hurt, but is it too much to hope for a bill of fare more elevated than soda and popcorn?
Nope. In fact, we’re pleased to report that your options for culturally infused (but decidedly unstuffy) excursions are all but endless in Central Florida. The following, then, are just a few after-hours jaunts that grownups will appreciate—from an upscale country music songfest to a pair of gregarious gallery treks that incorporate happy hours.
Nashville Night In Orlando
Roger Miller was so well known for spouting memorable quips that could be used as lyrics that artists and songwriters alike would jostle to sit on the barstool next to him so they could scribble down some of the hit-worthy phrases that he would utter so effortlessly.
According to one story circulated in Nashville, Kris Kristofferson made a forlorn comment one evening about having nothing left to lose. Miller took another chug-a-lug and replied with a shrug: “Nothin’ ain’t worth nothin’, but it’s free.” Bingo!
The writing and recording process is much more businesslike these days in Music City. But there’s still a story behind every song. Which is the idea behind Nashville Night in Orlando, where the writers of today’s chart-toppers swap songs and tell stories on the stage of Judson’s Live at Dr. Phillips Center.
Nashville Night is the brainchild of Orlando native Jay Peeper, who attended Boone High School and graduated from FSU (he was a sociology major) before landing a job as sales manager in the Atlanta office of Freeman, a global company that stages live events, exhibitions, conferences and trade shows.
“The music scene was great in Atlanta,” says Peeper, who had reconnected with aspiring songwriter Tyler Reeve, his college buddy (and, at the time, a fellow Atlantan) who earned a following through performances in small local venues—mostly bars. “I guess you could say that I was Tyler’s unofficial manager at the time,” says Peeper, who arranged many of those early gigs.
Reeve would later move to Nashville and write such hits as “Whiskey on My Breath” for Love & Theft, “I Got Away with You” for Luke Combs and “In Case You Didn’t Know” for Brett Young. The two stayed in touch after Peeper, who grew tired of the travel his job required, moved back to Orlando in 2008 and became a stay-at-home dad.
He wanted to get back into the music scene except, he noticed, there wasn’t much of a music scene to get back into. “Something was missing in Orlando,” he says. He came up with the concept for Nashville Night after talking to Reeve about the songwriter showcases that were staples of such Nashville institutions as the Bluebird Café. Why not give it a try?
So, in 2018, Peeper contacted Harry Buffalo, a sports bar on Church Street in Downtown Orlando, and pitched its management on the idea. The venue was on board, so Peeper booked Reeve—by then an established hitmaker—and fellow songwriter Johnny Bulford, a UCF graduate (and, like Peeper, a high-school Boone Brave) who had penned “Lonely Eyes” for Chris Young and “A Woman Like You” for Lee Brice.
“I figured if this didn’t work, then nothing would,” says Peeper. “I tried to make it a real Nashville-type experience. Just as Nashville as it could be.” The event quickly sold out, demonstrating that there was indeed a local audience for acoustic country music performed by the writers.
Peeper staged about a dozen shows at Harry Buffalo and, when that venue closed, moved his operation to Tuffy’s Music Box & Lounge in Sanford. But Tuffy’s was more suited for traditional concerts. Although his shows there were successful, Peeper preferred a vibe that better suited the intimate format: a pair of musicians with only their guitars (or perhaps a piano) playing for a roomful of friends.
He asked if anyone had suggestions via a post on Facebook in January 2024. Sure enough, someone did. Dr. Phillips Center Senior Director of Marketing Janet Ray thought she had just the place: Judson’s Live, which had recently opened. “It seemed like the stars just aligned,” says Ray. “Jay had this wonderful product, and we had this wonderful venue.” Peeper, of course, agreed—and in April of last year Judson’s Live hosted its first Nashville Night.
On the bill was Matt Jenkins, who had written seven No. 1 singles including “Happy Anywhere” for Blake Shelton and Gwen Stefani, and “Buy Dirt” for Jordan Davis and Luke Bryan—which was also named the Country Music Association’s Song of the Year in 2022.
Onstage with Jenkins was J.T. Harding, who had written such hits as “Somewhere in My Car” for Keith Urban, “Somewhere with You” and “Bar at the End of the World” for Kenny Chesney, “Different for Girls” for Dierks Bentley, “Alone with You” for Jake Owens and “Sangria” for Blake Shelton. The show was sold out, which has also been true of every subsequent incarnation of Nashville Night.
Reeve initially ushered Peeper into the close-knit world of songwriters in Nashville, but now the top tunesmiths on Music Row are clamoring to get booked at Judson’s Live. “We try to do it the right way,” says Peeper. “The venue is perfect, and the audiences are respectful and engaged. It’s a great musical experience whether you’re a fan of country music or not.”
So, in 2025 there’ll be an expanded slate of eight shows that got underway in February with, appropriately, Tyler Reeve and Justin Wilson, whose No. 1 hits include “Kiss You in the Morning” for Michael Ray and “Drunk Me” by Mitchell Tenpenny. They’ll be followed on Friday and Saturday, April 11 and 12, by Jordan Walker and Jerry Flowers, who’ve each written multiple blockbusters for the likes of Jason Aldean, Luke Combs, Sam Hunt and Keith Urban.
Artists haven’t been announced for the remainder of the series, but dates are Friday and Saturday, May 9 and 10; June 13 and 14; July 11 and 12; August 8 and 9; September 12 and 13; and October 10 and 11. Usually, shows are at 4 and 8 p.m. with seating beginning an hour beforehand. Tickets are priced starting at $67.50 and generally there is either a one-drink or a $25 food and beverage minimum per person.
Dr. Phillips Center is located at 445 South Magnolia Avenue, Orlando. For more information, call 407.358.6603 or visit drphillipscenter.org.
Happy Hour Tours at the Alfond Inn
At the Alfond Inn, a boutique hotel owned by Rollins College, you can combine a refined happy hour with a mind-expanding guided tour that encompasses some of the most outstanding (and sometimes provocative) pieces of contemporary art anywhere.
“The Happy Hour Tours are a way to encourage the community, as well as hotel guests, to engage with art in an alternative setting,” says Gisela Carbonell, interim director and curator of the Rollins Museum of Art.
The art on view at the Alfond was a gift to the college from Barbara and Ted Alfond (Class of ’68) and is a part of the museum’s permanent collection. Works at the inn are rotated once a year and generally consist of about 100 items that can be found in quite literally every nook and cranny. (The museum’s main facility is on campus, while the hotel is considered to be a satellite location to showcase the institution’s contemporary art holdings.)
Upcoming tours will feature works by Jeffrey Gibson, who represented the United States in the recent Venice Biennale—a prestigious international cultural festival held in Venice, Italy—as well as works by, among others, Amy Sherald, Tomás Saraceno and Mohammed Sami. The genres represented include painting, photography, sculpture, mixed media and other forms.
Carbonell says that the tours, which have been going on for about 10 years, are intended to be “educational experiences that also provide a space for dialogue and casual conversation between the tour lead and the group, and between attendees as well.”
Happy Hour Tours, which last about an hour, leave from the hotel lobby at 6 p.m. on the first Wednesday of each month. The events are free and open to all ages, but you’ll need to sign up at least two weeks ahead of time.
Adds Carbonell: “This is a great date-night activity. You can stop by the lounge/bar area, purchase drinks, attend the tour, learn about the art and the artists, and then head to dinner at Hamilton’s Kitchen.” That’s the hotel’s critically acclaimed restaurant, which has become known for its creative cuisine and impeccable service.
The Alfond is located at 300 East New England Avenue, Winter Park. For more information, call 407.646.2526 or visit rollins.edu/rma/learn/lectures-tours.
Open Studio Night at the Gallery on First
Open Studio Night at the Gallery on First in Sanford—the successor to the community’s original Art Walk—is a free drop-in event held the third Saturday of each month. But, because each event features a different creator among the funky facility’s 14 studio-artists-in-residence, you’ll want to go as often as possible.
“The evening always has an air of spontaneity,” says Bailey Wight, manager of the gallery. “You just never know what will happen next.” Plus, you’ll be able to mingle with artists, enjoy a drink and soak up the ambiance of the 139-year-old Hotchkiss Building. (Gallery on First shares space with Jeanine Taylor Folk Art.) You’re welcome to simply show up any time between 6 and 9 p.m.
Gallery on First is both a gallery and a working space for professional and emerging artists who are eager to share the artistic process with anyone who’s interested through education and events.
The artists—whose work spans every imaginable discipline—welcome people into their creative inner-sanctums to chat about their latest projects or to debut new works. “We try to make it fun for the artists and guests,” says sculptor and abstract artist Kevin Abbott, who shares a studio with his wife and fellow artist Debe Abbott.
After perusing the gallery and conversing with the featured artists, step outside and look along the side of the building for a mural designed by Mark Seppala and painted by gallery artists Stewart Jones, Julie Latayan, Charlie Ramos, John Sullivan and Cindy Sturla.
The mural features colorful suns, flowers, butterfly wings, agricultural products and multiple small images of Jeanine Taylor’s cute French bulldog, Louie, whose visage is innocuously scattered throughout. It’s a wonderful place to steal a kiss or snap a sweet selfie with your companion for this artsy evening.
Gallery on First is located at 211 East 1st Street, Sanford, in the heart of the Downtown Historic District. For more information, call 407.323.2774 or visit galleryonfirst.com.
