A Mighty Hootenanny: Anastasia Music Festival, the New Jamgrass Giant

written by Connor Hayes

photos by Connor Hayes

St. Augustine may be home to several music festivals and two-night concert events, but this brand new progressive and traditional bluegrass festival could be it’s most intimate, most care-free, and by far it’s most family friendly.  There couldn’t be a more perfect location for such a hootenanny: The Ancient City, as it is called, home to a bustling tourist industry that hasn’t overrun or sullied its penchant for the quirky, genuine, and weird.  Anastasia hits two out of those three; there’s nothing weird about dancing barefoot on the deck of the newly inaugurated Front Porch Stage to some sweet New Orleans style jazz-folk fusion.


Music Genre – Traditional Bluegrass, Progressive Bluegrass, Jam Grass, Jazz Fusion, Folk, Indie.

Camping – Lots right next to the venue, by way of Anastasia State Park, home to all kinds of healthy after hours fun (we’ll get to that in a bit)

Capacity – Very Small (2.5k – 5k)

Crowd Type – Deadheads, Jam Grass fans, Bluegrass aficionados, Families

Water Stations – Yes


For the First Timers – Although all considering everyone is a first timer to Anastasia this year ‘round, those new to St. Augustine and the Amphitheater grounds will have no shortage of places to go and things to see.  As parking in the city is hard to come by, for any historic city with a heavy tourist industry, there exists parking garages on the north side of the Old City.  You shouldn’t stress so much about getting to the venue and finding parking: the parking lot is built to accommodate a capacity crowd (2,500), and numerous street parking opportunities exist as well.  When you’re ready to take a break from the Amp itself, ample green sitting space exists right outside the main building, as well as across the Bridge of Lions on the grounds of the Spanish-built Castillo San Marco.  Feel free to browse all the shops and markets on St. George Street, the bustling heart of the Old St. Augustine.

Standout Food (and Drink) – Although there’s enough culinary pleasures to sample in St. Augustine to last a lifetime, Anastasia also had it’s share of treats.  A Middle-eastern style stall with gyros and falafel was in attendance, and so were numerous drink bars, with everything from fruity cocktails to IPAs.  Of special note were the beverage cups being bigger than your average festie beer stand, which pleased many attendees.

Musical Highlights – One would think that for a fest that relies on heavily one genre, the talent would become repetitive by the end of the day, but as the festival went by, it was very apparent that each and every band brought something different to the table, whether it was David Grisman stopping between songs to tell the audience the history of bluegrass, or the Fleetwood Mac-esque group, Paper Bird. Here’s some of the performances that really got the crowd going:

  • Del McCoury – The Bluegrass legend outdid himself at Anastasia, providing not one, but TWO full length sets.  What made these different from, say, a Del Fest set, was that the majority of Friday nights set was all requests.  The audience interaction with Del was absolutely something out of a family gathering, which is what a Del McCoury set feels like anyway.
  • Sam Bush – The father of progressive bluegrass, and my personal dream set, took the stage on Saturday night, and the rest is history.  Bush played one of his most breakneck tunes, “Play by Your Own Rules”, right out of the gate, and then reprised Allain Toussaint’s classic “Sneakin Sally Down the Alley” (which is ironic because almost a year ago Chris Robinson’s Soul Revue did the same tune on the same stage).  I had high hopes for Bush’s set, and yet even those were utterly upped by his skill with the mandolin and his insanely executed jams
  • The Grateful Ball – This rare event features Del’s sons, The Travellin McCourys, and Jeff Austin of Yonder Mountain fam playing bluegrass renditions of the Grateful Dead’s discography, and lord have mercy, they burnt down the house.  Whether it was “Scarlet Begonias”, or “Loose Lucy”, or even a haunting and legendary finale of “Fire on the Mountain”, Saturday night left the whole crowd feeling grateful.

Things to do

  • Lounge on the Front Porch Stage
  • Ask Phish and Dead fans about their war stories
  • Enjoy a St. Augustine Sunset
  • Browse the Wormtown Trading Co.’s wares
  • Get down to the talent on the Acoustic stage

VIP or Nah – VIP is recommended.  The Amp’s VIP lounge is the same as it is for many other festivals held on the grounds, but theres just something about the wooden garden lattice structure and the linen-covered coffee tables, located right past main stage, that makes for a wonderful way to enjoy the festival, without leaving the music.  Their bar is many shelves above the regular fare offered in front of the Amp, with top shelf bourbon, rum, and whiskey offered, at affordable rates.  Plus there’s the chance to meet musicians hanging out as well.

Story Corner – Del McCoury was the flashpoint of my journey into bluegrass many, many years ago.  Seeing him live again for the first time since 2013 was incredible, but even better was running into him at the Front Porch stage.  He had come to see his son’s set, which I thought was the most amazing thing.  On Friday night, he also brought his grandson Evan McCoury, so at one point there were 3 generations of bluegrass on one stage.  Of course I didn’t cry (I’m also a horrible liar).

Check out the full photo gallery from Anastasia Music Festival here!

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