Do Good – Every Jam Saves The Bay

A saying on a sticker someone gave me (at a music festival of course) that I try to actively incorporate into life as much as possible.  The Annapolis Baygrass Festival, for the third year in a row, made that entirely too easy.  Including all three elements into the foundation of the event that has continued to grow, is what organizers managed to execute flawlessly at the 2025 rendition.

Do Good – Every Jam Saves The Bay

Not only does a portion of every ticket, drink purchase, and Baygrass merch sold go directly to the non-profit partners recognized repeatedly throughout the weekend, but the setting also raises awareness.  Organizations working to restore and protect the Chesapeake Bay could provide actual proof and evidence of the needs, impact and results of their efforts all around Sandy Pointe.  Workshops to further educate attendees and even a giant balloon  flying high in the sky reading weather patterns were just a few of the opportunities available to learn more about the Chesapeake Bay waters and why we all need to ensure it is well taken care of.  Baygrass makes its mission a living, breathing part of the weekend that locals take notice of and appreciate wholeheartedly.  Making the festival green by having a zero plastic motto as well as volunteers standing ready to help sort compostables, trash and recycling paid some good karma forward in the eyes of Mother Nature. 

DCMR had the opportunity to sit down and chat with Kyle Hollingsworth, who himself is home-grown and familiar with all the life that depends on the water source, being from Maryland.

DCMR: “So you’re from the area, what was your favorite venue to go to growing up?”

KH: “Well, my first band Black Friday, played at the 8 x 10, many years ago, this is in the 80s, when Giles was actually the owner.  We would play there because we would have a draw,and he'd pay us, but we were not legally old enough to be in the club.  I was the oldest at eighteen and the other guys, some of the other guys were only sixteen.  So we would play and then immediately have to leave.  In DC, we played 9:30 Club and then we also played The Bayou.”

Feel Good – Beach Yoga & Mental Health Awareness

You have to take advantage of being in such a beautiful spot so not only did we learn how to keep the Chesapeake healthy for years to come, we also made sure that we do as well.  Yoga sessions on the beach with toes in the sand while bands played not even fifty feet away is an activity that doesn’t come along every day.  

Organizers of the event are also big supporters of Mental Health Awareness and held a workshop focusing on how it’s sometimes “ok to not be ok” lending understanding and support on how to get through some of the struggles. Both Saturday and Sunday also had several reserved times for Sober Gatherings to further incorporate and provide for the attendees who chose to take that route.

Make it Fun.  Music and People.

There wasn’t a single person that I saw or spoke to the entire weekend that wasn’t having the kind of time that we all wish for more of.  The lineup this year brought in some artists that expanded past just Bluegrass like LaMP, but also had the staple festival regulars playing all over the musical map.

Larry Keel’s Electric Larry Land and the Grateful Ball featuring the Travelin McCourys got downright funky and Kyle Hollingsworth really turned it up with his mid-afternoon set on Sunday.  Paying homage to a wide variety of artists from all over the musical map, bands went left, right and center with some of the covers they brought out for the weekend.  

Hollingsworth just released a new album and described it as a mash up of different sounds throughout.

DCMR: “So the new album is out and it’s called All We Are.  So what all are we – is it sugar and spice and everything nice?  Or more like Jameson on ice?”

KH: “So, it's the title track of my album, and so I was looking for the way to represent all the songs on the album. The first song is a little bit Death Cab For Cutie, a little bit indie rock. I was a little nervous to put that one first, but then everybody at the record company really liked it, liked that style.  Then I do like a funky number and then I'll do a Paul Simon type of thing, so it’s all we are - it’s a concept of all the musical influences in my life.”

Not only are his musical influences a long, diverse list but so are his musical instrument playing capabilities.  

DCMR: So a lot of instruments that you play - accordion, keys, ukulele – the list goes on. So, what is one that you don't know how to play yet that you want to still learn?

KH: Oh wow, good question. I was thinking about this just the other day because I just started playing ukulele, and that's really fun to write on. Something that I would love to play…. well, I definitely want to play accordion better, but maybe something like a Dobro or something that has, like, the way you can be emotional and bend notes that the piano players don’t really have a way to do that too easily.

As always, old friends reconnected and caught up, and new friends were made just the same.  That goes for off-stage in the crowd, but on-stage as well, where ticket holders were once again blessed with Holly Bowling joining Kyle Hollingsworth and making even more music magic during their Saturday night set.  Both Bowling and artist-at-large Kyle Tuttle shared stages a-plenty throughout the weekend, dazzling us all over and over again.  

Baygrass has improved their lineup, experience and environmental awareness as well as impact year after year and provided a late-Summer/early-Fall event that we cannot wait to continue being a part of and see what they’ll give us in 2026!