As summer fades into fall, my journey takes me to the shores of the Chesapeake Bay and Sandy Point State Park for the annual gathering of the Annapolis Baygrass Music Festival.

The setting provides a scenic view of the Chesapeake Bay to the left of the stage with ships navigating their way up and down the Chesapeake Bay and a Sandy Beach for the young ones and old to sit on and play. This festival works in conjunction with many of the Chesapeake Bay conservation efforts, a positive vibe for me being from this area. This year had another excellent lineup. I can only attend one day this year and from what I heard, I missed out on some great music on Saturday, but Sunday was stellar.

Saturday opened up with Geraldine followed by Elliot Peck and friends. One thing nice about Baygrass is the stages or side-by-side and there is very little downtime between the music. Sam Grisman Project followed by Larry Keels Electric Larry Land, with Lamp the band Kitchen Dwellers and finished up the evening with a double set from Greensky Bluegrass. Just an awesome lineup for an opening day. Artist at large for the weekend were Holly Bowling, Kyle Tuttle and Patrick Rainey.

 On Sunday, I arrived early anticipating a full day of friends and music. No sooner than I arrived at the gate, I was able to reconnect with several friends and even some of the staff at check-in. By the way, the staff there is very accommodating and professional. Upon checking in, I posted up near the soundboard and was ready to start my day.

After the opening ceremonies and the National Anthem we got right into the music. Opening up, the day was home town band Pressing Strings. Although they are a national touring band, Annapolis Maryland was their home. 

The Last Revel took to the stage next. This Minneapolis based bluegrass group brings an energetic uplifting foot-stomping sound that I have come to fall in love with. After the Revel it was time to open the stage up to The Travelin’ McCoury’s. There is not much I can say about one of my favorite bands that hasn’t already been said, Ronnie and Rob with Alan, Colby and the newest member Christian were playing two sets this day and bright the crowd to their feet with much dancing and positivity. 

Kyle Hollingsworth Band was next up, the keyboardist brought the jams. As a member of the String Cheese Incident, Kyle has brought out several albums through the years with his own band and continues to produce his sound. 

Then it was time for the Travelin’ McCoury’s to do their Grateful Ball set. This is always a crowd pleaser as I saw many people dancing and singing along with the band. After the McCourys it was time for Molly Tuttle to bring her new rendition of her band to the stage. The Grammy award winning Tuttle played all of our favorites, including a few with former bandmate and artist at large Kyle Tuttle.  

Now it was time for the the final band of the day and one of my absolute favorite bands, Railroad Earth.  As they opened up with “Long Way to Go,” I was having trouble singing and dancing while trying to hold my camera. Such a joy to see these guys again!

Another great festival put on by the Shores of the Chesapeake, great weather, beautiful setting, great friends, and outstanding music. I would recommend all my friends and anyone else to try to attend the Annapolis Baygrass Music Festival in the future as announced by MC and host John Way, they have approval for next year. 

Get out and see live music folks.

Check out more photos from the 2025 Annapolis Baygrass Festival on September 21, 2025. All photos are copyright Frank Thompson: