Music, Memories, and a Mission: Baygrass Festival Unites Fans for the Chesapeake Bay
Words by Dan Rozman
Photos by Mark Raker and Brett Armstrong

What’s better than spending a perfect fall weekend at the beach? How about adding some amazing bluegrass music to the mix? That’s exactly what happened at the second annual Annapolis Baygrass Music Festival, held right on the shore of the Chesapeake Bay. Leftover Salmon’s Vince Herman summed up the excitement as he arrived: “What a beautiful place to be, a bunch of our friends are here, and this looks like this is going to be some kind of fun. Great turnout and beautiful weather.”

This year’s festival was even bigger and better than last year. Imagine standing on the sandy beach at Sandy Point State Park, feeling the breeze off the water, and watching the huge Bay Bridge stretch across the water while incredible musicians played their hearts out on stage. Kids splashed in the bay, families spread out picnic blankets, and the smell of delicious crab cakes filled the air.

At Sandy Point State Park on Sept. 21, the festival kicked off with Baltimore’s own country-leaning string band, Geraldine. The Lil Smokies, drove all the way from Martinsville, Virginia, to play an early set. Jake Simpson from the band was excited to be there: “We’re stoked to get here and play early so we can see the rest of the day. Sierra Hull is one of my favorite artists to watch, and of course, Sam Bush, how can you go wrong?”

The band treated fans to favorites like “California” and hinted at what’s coming next. Jake shared some exciting news about their upcoming album, due out in February: “During the pandemic, we all wrote a bunch of songs. It’s a little bit of a departure from the music that we’ve released in the past, but so far, it’s my favorite album that we’ve made. It’s a beautiful album with some really authentic songs that represent us in the time that we’re at right now.”

The festival had two days packed with awesome performances, made even more special by the artists-at-large who popped up throughout the weekend. Jennifer Hartswick, Natalie Cressman, and Ron Holloway brought their amazing brass skills to several sets, adding an extra punch of funk and jazz to the bluegrass sounds. They truly showed their stuff during Trouble No More’s set, joining in for an electrifying version of “Whipping Post” that had everyone dancing.

Sierra Hull amazed everyone with her incredible talent, living up to Jake Simpson’s excitement to see her perform. During his workshop, Sam Bush shared fun stories between songs, making it feel like we were all just hanging out with an old friend.

Watch Sam Bush perform “Howlin’ at the Moon” for Kentucky Educational Television on YouTube:

Saturday night ended with a performance by Oteil and Friends, featuring two amazing sets. Oteil was clearly feeling the festival’s special vibe, telling the crowd, “This is what music is all about — bringing people together, celebrating life, and doing some good for the planet while we’re at it. The Chesapeake Bay is a treasure, and we’re all here to help protect it.”

On Sunday morning, the Baygrass festival kicked off with a performance by the Dirty Grass Players, marking Alex Berman’s final show before taking a hiatus from the band. One of the coolest moments happened during Cris Jacobs’ set when he invited Daniel Donato to join him on stage. The two guitar players traded licks back and forth, creating an impromptu jam that had the whole crowd mesmerized. Donato, who later rocked his own full set on Sunday, said: “There’s something magical about playing music right here on the bay. The energy from the crowd mixed with the natural beauty of this place — it’s unreal!”

Watch the official music video for “Heavy Water” by Cris Jacobs on YouTube:

Baygrass isn’t just about having a good time and saving the bay (though there was plenty of both!). This year, the festival also focused on taking care of each other. Working with The VA Way, a charity that supports veterans’ mental health, Baygrass spread a message of self-care and looking out for one another. Between sets, musicians and organizers reminded everyone that just like we need to protect the bay, we need to protect each other too. They even had a quiet area where people could take a break if they needed to recharge.

What made Baygrass really special was how friendly everyone was. Musicians hung out to watch other bands play, festivalgoers made new friends while waiting in line for food, and kids danced together near the stage and in the kidzone. The entire weekend felt like a big family get-together with really good music! As the sun set on Sunday evening and The Infamous Stringdusters closed out the festival, it was clear that Baygrass 2024 was a huge success. Travis Book from the Stringdusters got everyone laughing and dancing, ending the weekend on the perfect note. Can’t wait for next year? Neither can we! As Ron Peremel said at the end of the festival: “Thank you to everyone who made this weekend so magical. See you all in 2025 for more amazing Baygrass experiences!”

Certain aspects of the research and/or drafting for this piece may have had AI assistance.

Here are photos of the first day of the 2024 Annapolis Baygrass Music Festival. All pictures copyright and courtesy of Mark Raker.

Here are photos of the second day of the 2024 Annapolis Baygrass Music Festival. All pictures copyright and courtesy of Brett Armstrong.