Josh Olmstead has been performing classical guitar professionally since high school, when he accepted his first monthly residency at the Renaissance Restaurant in Watertown, New York. Since then, he has performed classical guitar in countless ceremonies, receptions, and dinner parties, including a wedding officiated by the Honorable Marjorie O. Rendell – the 43rd First Lady of Pennsylvania – at the National Constitution Center.

Josh Olmstead’s other notable performances have included grand events at the Pennsylvania Academy of Fine Arts, Stotesbury Mansion, and Samuel Powel House in Center City Philadelphia, the Barns at Wesleyan Hills in Connecticut, and the State Street Bank building in Boston, as well as intimate affairs at the Philadelphia Cricket Club, Ridgeland Mansion and Valley Green Inn in Philadelphia’s Fairmount Park, the Farmhouse at People’s Light & Theatre in Malvern, Pennsylvania, The Chelsea in Atlantic City, and Emerson Inn by the Sea in Rockport, Massachusetts.

His customers have included American Veterinary Medical Association, BalletX, Brandywine Ballet, Flex-Time Lawyers, Future Brands, Jimmy Duffy Catering, Liberty International Underwriters, Southern Wine & Spirits of PA, Starbucks, Wharton School of Business, among many others.

Josh Olmstead has also performed music for holidays and special occasions at some of Philadelphia’s finest restaurants, including Bistro St. Tropez, Cake, Patou, Rittenhouse Hotel, and Susanna Foo. Additionally, he has provided classical guitar for seniors at the Abramson Center for Jewish Life and Plushmills Independent Senior Living Community.

Josh Olmstead, a cum laude, Phi Beta Kappa graduate of Temple University, received the Robert M. Greenberg Memorial Award in American Studies, and his B.A. in American Studies/Minor in Music in 2002. While enrolled at the conservatories of Purchase College and Temple University, he studied classical guitar performance under David Starobin (Curtis Institute of Music), William Anderson (Sarah Lawrence University), and Allen Krantz (Philadelphia Orchestra lecturer). During college, he was a regular participant in weekly master classes, department recitals, and guitar ensemble performances, as well as a member of South Philadelphia’s Munier Mandolin Orchestra. Josh Olmstead trained for his conservatory auditions with Alexander Raykov at Saint Lawrence University and Glen Lyons at West Chester University.

With a vast repertoire of Spanish, Italian, German, and Brazilian selections, encompassing the Baroque, Renaissance, Classical, and Romantic periods, Josh Olmstead’s guitar is sure to imbue your next event with the distinct elegance and refined musical accompaniment your guests have come to expect.

Contact Josh at or (267) 303-6831 to discuss your event today. In the meantime, please feel free to listen to the short classical guitar samples and read the testimonials provided below:

Fernando Sor, Opus 35, No. 22

Francisco Tárrega, Lágrima

Matteo Carcassi, Opus 60, no. 3



Working with Josh was incredible for our wedding. During a time when managing most people is a royal pain in the sweet biscuits, Josh was perfect. He’s an incredible artist, that was unexpectedly on time, on budget, and highly responsive (sorry to knock artists). He thoughtfully executed everything we communicated. His presence and classical guitar breathed a soulful warmth into our special day that far surpassed our expectations.

– Ty & Jenny Burrowbridge

Josh is an exceptional musician and an absolute joy to work with! He was friendly, professional, and extremely accommodating.

We knew that we wanted something special for the processional music, but were wrestling with how to keep the mood casual and fun, without losing out on a sense of formality and eloquence. We also knew that we were not interested in conforming to the traditional wedding marches, but we were unsure what could take its place. Fortunately, Josh came to the rescue! He was able to suggest and send us sound clips of various examples, along with written descriptions, so that we could get a feel for what the songs would sound like and what feeling they would provide. 

On the day of the wedding, Josh arrived ready to play. All we did was point him in the direction of where he would be sitting and he took care of everything else. Josh was setup and ready to go with plenty of time to spare. He even lent us an extra microphone stand for the officiant, a small detail we overlooked.

Josh played several classical pieces while the guests were being seated and the wedding party was taking their places, a special selection for the bride, and, at the end of the ceremony, he played us all out and didn’t stop until the last guest had also left.

We cannot say enough good things about Josh. He was a perfect addition to our wedding ceremony! I wish we could just have him come and play for us every weekend!

– Logan and Michelle Chieffo

Josh has performed for us as a solo act and with a band many times at parties, fundraisers and political events. He has a perfect feel for the audience and tailors his material to their tastes. He’s a great musician and singer and is the rare performer that can work in rare and even original material while still keeping the audiences’ interest. He’s also very gracious about requests. 

Josh’s live performances make a special event even more memorable because he customizes his playlists and delivers a great sound. He just gets it right every time! 

Josh is an even better person than he is a musician. I recommend him without any hesitation. You’ll love it!!

– Jim and Nora Eisenhower

When planning our ‘big day’ we were trying to make everything perfect and specific to ‘us’…the tables looked nice, the clothing was pretty, the food was delicious… but something was missing. One of the biggest events of the day is walking down the metaphorical yet physical “aisle”… when envisioning this moment beforehand, something was missing. We contacted Josh and talked to him about playing our favorite classical pieces as we were walking down the aisle… he put together a beautiful arrangement and sat under a willow tree playing his classical guitar as the wedding party filed into our ceremony… our day was complete… I’m welling up as I type this…thanks Josh.

– Jon and Ashley Rundstrom