Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Inaugural Annapolis Baygrass Festival Already Feels Like Home: REVIEW

by Oct 8, 2023Featured, Music, Reviews

The 2023 Annapolis Baygrass Music Festival took place at Sandy Point State Park in Annapolis, Maryland on September 30 & October 1. Headliners included Yonder Mountain String Band, Railroad Earth, Keller & The Keels, and Melvin Seals & JGB.  

Annapolis Baygrass 2023 Proved That First-Year Festivals Can Feel Like Home


We are no strangers to music festivals.  In fact, one could say that we have sort of made it a lifestyle.

We know that not all festivals start out with a bang.  It takes time to get the details just right;  get the bands just right; all to curate a vibe that is just right.

Some might say that it’s wise to go into a first-year festival with little expectations (and, as such, you won’t easily be let down 🎶 ).

Hundreds of attendees walked through the entrance gates at Sandy Point State Park on Saturday, September 30th.  They had no vision of what the festival grounds would look like.  They had no feeling of what energy the festival would convey.  They had no notions of what to expect.

It would be safe to say that some were pleasantly surprised, but most were completely blown away.  Because Annapolis Baygrass Festival decided they weren’t going to be a first-year festival.

In fact, Annapolis Baygrass created what can take other festivals years to grow:  a festival that feels like home. 


Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals


Our favorite festivals are the ones that manage to incorporate three main elements:  The Music, The Culture, and The Adventure.

Annapolis Baygrass Music Festival hit all those sweet spots that came together into one big fuzzy feeling.

The result?  Bands and artists with a deep connection; staff and volunteers who worked together like a family; a goal to give back to the community and the environment through the festival efforts; and all at a location that merged the soothing waters of the Bay along with the grassy comforts of your favorite park.

The Music: Bluegrass and More on the Chesapeake Bay

From the very first note of music, festival attendees could feel that something special was about to transpire.

Geraldine kicked off the “Every Jam Saves The Bay” Stage on Saturday morning, and it couldn’t have been more symbolic.  Baygrass Festival set a mission to ensure that this festival would have a positive impact on the surrounding environs (namely the Chesapeake Bay), and Geraldine helped to convey that message through the power of music and lyrics with the festival’s theme song,  “In the Water”.

Watch the video for the official Baygrass song “In the Water”: 


Anchors Aweigh! The first Baygrass festival was officially live. ⚓️

The Dirty Grass Players, a fast-paced newgrass band from Baltimore, brought the heat to kick off the Baygrass Stage, which was conveniently located directly next to the “Every Jam Saves the Bay” Stage.  Throughout the day, the bands alternated between the two.  The result was a continuous flow of no overlapping music, so nobody had to miss a beat.

As the sun broke through the morning cloud cover,  you could feel the festival was just getting warmed up.  Jon Stickley Trio had us all dancing as we admired the beautiful views across the Chesapeake Bay Bridge.   Immediately following that set, fiddler Lyndsay Pruett headed right across to the neighboring stage to join forces with the Lindsay Lou Band (because that’s how you Pruett!). The festival’s Artist-At-Large, Lindsay Lou also played an entire set of music with her all-female band, which included Mimi Naja (Fruition), Michelle Pietrafitta (Banshee Tree), and Heather Gillis (Wolf Twin).   Audience members received a special performance of Lindsay’s newly released album, “Queen of Time” in its entirety.

It seemed like the celestial beings wanted their own festival performance.  As day shifted into night, we were blessed with a collage of colors when the sun dipped under the bay, contrasted by the rise of deep orange and reds as the harvest moon rose into the low clouds.

Night time is the right time.


Jon Stickley Trio at Annapolis Baygrass Music Festival 2023 | Festy GoNuts

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Lindsay Lou at Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Railroad Earth, Keller and the Keels and Yonder Mountain String Band had been on the road together for the past two weeks as part of a combined fall Relix tour.  The final tour stop was at Baygrass Festival – and it’s hard not to think that they saved the best for last. 

When Railroad Earth plays their sweet soulful tunes as the waves lap up on the shore, it just feels like magic.  (If you have been lucky enough to attend Strings & Sol, you know what I am talking about.)  So, having Railroad take us into the evening at Baygrass Festival felt very familiar.  The Bay breeze seemed to intensify in coordination with Tim Carbone‘s fiddle, and we all swayed with the rhythm and flow of the water.

If you weren’t sure if Baygrass felt like home already, you were  convinced when Todd Shaeffer began singing “Happy as a family, happy hand in hand, happy as a family singing.”   “Fisherman’s Blues” and “Chasin’ a Rainbow” seemed to envelope us all in the beautiful bayside setting.  Then Lindsay Lou joined in for their final tune, “How Sweet It Is (To Be Loved By You)”.

If you didn’t hug a stranger by then, what were you thinking?

We all floated a few steps away to the other stage as Keller & The Keels took over.  Keller Williams fits in seamlessly on stage with Larry and Jenny Keel, all three with roots in Virginia.  The trio put a little pep in our step with Jenny’s bass-heavy beats, Larry’s fiery flat-picking, and Keller’s lightning-speed lyrics.  The set felt right at home with this DelMarVa crowd.

Yonder Mountain String Band played the grand finale set for the three-band tour, and wrapped up our Saturday night at Baygrass.  It seemed only fitting that Yonder Mountain close out day one of the first Baygrass Festival, since they were the original headliners of the 2022 Baygrass (which was sadly canceled due to the hurricane).  The core members of Yonder Mountain have been playing together for decades, truly a family of musicians with a huge history.  But even the newest additions seemed right at home on stage. Nick Piccicini absolutely owned the mandolin, while Coleman Smith (RapidGrass) raged with his high-speed fiddle playing.  (Did I hear chants of “Keep Coleman” resonating from the crowd?)  Lindsay Lou brought her powerful vocals to the stage for “What the Night Brings”.   

The evening came to a close with all of Railroad Earth joining Yonder for the crowd-pleaser, “Dancing in the Moonlight.”

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Railroad Earth and Lindsay Lou at Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Yonder Mountain String Band at Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

We rolled into Sunday off of the highs from Saturday’s festivities.  The High and Wides did not give us an easy-like-Sunday-morning set, as they kicked off the day with a barn burner to warm up our dancing legs and make it clear just what we were doing here. 🎶  Day 2 was off to a strong start!

The three ladies from Wicked Sycamore came to the stage next, all dressed to impress in hot pink.  We loved seeing this band on stage and in the crowd, truly being a part of the festival family.  Lindsay Lou joined in for “I Wanna Dance With Somebody” – and we couldn’t help but sing along.

Arkansauce apparently got the memo that there were no Sunday sleepers at this festival.  This 4-piece from, you guessed it, Arkansas is quickly becoming our new favorite fast-grass string band.  They bring big-band energy to the stage, and some of the friendliest vibes off-stage.

Fully warmed up by now, the crowd was ready to welcome their hometown favorite to the stage, Cris Jacobs with Smooth Kentucky.  Called “The King of Baltimore rock ‘n roll” by Baltimore Magazine, some fans might have been surprised to see Cris play a bluegrass set.  But his roots are with the bluegrass group Smooth Kentucky, his original band from the early 2000s.  And, of course, Lindsay Lou joined in on a few songs from Cris’ upcoming album, as well as an absolute fire version of “Little Maggie.”

Annapolis Baygrass Music Festival 2023 | Festy GoNuts

Wicked Sycamore at Annapolis Baygrass Music Festival 2023 | Festy GoNuts

Annapolis Baygrass Music Festival 2023 | Sam Watson

Cris Jacobs & Smooth Kentucky at Annapolis Baygrass Music Festival 2023 | Sam Watson

Up next was Cabinet, and we were all ready to get high on some PA bluegrass.  Since Festy GoNuts is based in Colorado, it is rare we get a Cabinet set (although we were lucky enough to catch them at Rhythms on the Rio in August, so we’re feeling pretty spoiled this year).   But we were born and raised in the PA/MD area, so Cabinet feels like a little piece of home every time we see them.  The Cabfam feeling was strong on Sunday, and we were yet again treated to a Lindsay Lou sit-in. (She took the role of Artist-At-Large seriously, folks!)

Fruition was the final set of the weekend on the “Every Jam Saves the Bay” Stage.  And what a set it was!  They played a full 90 minutes, kicking off with a long list of new songs that already felt like familiar Fruition tunes.  Seeming surprised by how much time they had left, the band continued to keep the hits coming.  We sang along with the crowd favorites, hugging our friends, dancing with strangers, and feeling all of the good Baygrass vibes.  Miss Lindsay Lou jumped on stage again for the newly dubbed “Santa Lou” (“Santa Fe” featuring Lou).

We weren’t done rocking yet, because the festival wrapped up with a power set from Melvin Seals and JGB.  The band was ready to kick off the first of an 11-show tour, and the crowd was ready to help Melvin celebrate his 70th birthday that fell just a few days prior.  “Cats Under the Stars” was the perfect soundtrack as the harvest moon rose high again into the starlit sky, while “Sisters & Brothers” reminded us that we are all one big family.  The “How Sweet It Is” encore couldn’t have more perfectly summed up our feelings as this beautiful festival came to an end.

This weekend proved to us that Baygrass doesn’t intend to be all bluegrass – and that’s our favorite kind of fest.  A beautiful mix of bluegrass, jamgrass, funk, blues, and rock ‘n roll means that there’s always a plenty for everyone to love.


Annapolis Baygrass Music Festival 2023 | Festy GoNuts

Fruition at Annapolis Baygrass Music Festival 2023 | Festy GoNuts

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Melvin Seals & JGB at Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

The Culture: This is Why We Baygrass

Annapolis Baygrass Festival was created by real people who are passionate about good music, inspired by their favorite festivals, and dedicated to family, friends and FUN. 

This was a project of love.  And it showed. 

When Annapolis Baygrass Festival was first announced to the public, it was a name, a date and a location.  By the time we all arrived at Sandy Point State Park, the term BAYGRASS had evolved. 

Baygrass became a verb.  An action, a state, an occurrence.  When we chose to attend Baygrass, we chose to Baygrass.  We were committing to not impacting the environment with our festival activities.  We were accepting that the Chesapeake Bay needs to be protected and restored. We were supporting the mental health of our friends, family and community. 

This is why we Baygrass. 

Baygrass became a community.  Friends and strangers coming together to participate in an inaugural event.  Being left with a feeling that we were all part of something that was going to evolve into something iconic in years to come. 

We were all Baygrassers.

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

As one looked around the festival grounds, it could be seen that there was careful consideration put into what the attendees would be offered beyond the stages. 

Everyone was welcome at Annapolis Baygrass Festival.

Baygrassers of all ages could be seen enjoying the activities. For the families who wanted to bring their young ones, the festival’s KidZone was a safe place to let them play, create and explore.  In fact, there were even games for the young-at-heart set up near the Baygrass Beer Garden.  If you were looking for more physical activity beyond dancing, you could join the daily yoga classes by Active Potential on the beach while listening to the sounds of the bay blend with the songs from the stage. 

For those who enjoy a good cocktail or a local brew, you were in luck.  Gray Wolf Spirits was serving up unique concoctions, Idiom and Pherm breweries were pouring drafts for every tastebud, and Wine Collective had a quality selection not typically found at a music festival.  If you weren’t into alcohol, mocktails from Sobar and non-alcohol beers from Untitled Art were just a few of the options you could imbibe. 

Annapolis Baygrass Music Festival 2023 | Sam Watson

Annapolis Baygrass Music Festival 2023 | Sam Watson

Food options at Baygrass were thoughtfully curated, and not at all the standard festival fare.  Eastern-shore-style seafood was definitely featured, but meat lovers and vegetarians were equally satisfied with the offerings.  Pretzels with crab dip, oyster poboys, pit beef sandwiches, brick oven pizzas – our bellies were as full as our hearts. (Hope you saved room for the Maryland-style snowballs and donuts!)

The VIP ticket holders were treated to an all-inclusive experience that elevated the already exceptional festival offerings.  Closer parking lots and a dedicated check-in line eased us into the festival itself.  When we entered the exclusive VIP lounge area, we were greeted with a welcome gift bag that had our steel pint cup, festival koozie and our drink coupons.  We enjoyed a buffet-style dinner, which featured exceptional Maryland-style crab cakes.  And the icing on the cake – a half-dozen freshly shucked raw oysters.  

GA ticket holders had a premium festival experience as well, once again reflecting on the thoughtfulness of the festival curators.  Every single attendee could relax under the shaded canopies, lounge on the beach, view both stages with ease, and enjoy a superior menu of food and drinks. 

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Annapolis Baygrass Music Festival 2023 | Festy GoNuts

Festy GoNuts and Jon Stickley Trio enjoy fresh raw oysters at Annapolis Baygrass Music Festival 2023 | Festy GoNuts

Perhaps the cherry on top of the festival was the intimate Workshop Pavilion StageYonder Mountain String Band kicked it off with a set about their life on the road.  Mimi Naja and friends played Gillian Welch songs to celebrate her birthday.  This was special: the bands and the audience all sitting down together to hear acoustic songs and stories, asking questions and getting personal answers, and truly feeling like a community. 

Beyond the music came the education classes from the non-profit partners that the festival worked closely with to support their missions.  Shucking oysters while learning how they are important to restoring the Chesapeake Bay’s eco-system, making rain barrels that inspire us to strive for clean water practices, and discovering how we can become environmental stewards through tree-planting were just some of the ways the festival focused on giving back to the area.  

Lindsay Lou took time to share intimate experiences with those who attended the Narcan training workshop, a nod to the festival’s mission to support and promote mental health programs in our community.  John Way, festival co-founder and owner of VAWay, also took time to open up to all in attendance about why he was so passionate about this cause.  It was a raw and emotional experience that showed just how inclusive the festival intends to be. 

The festival founders put their mission’s words into action throughout the weekend.  The workshops connected the artists and the attendees with the core festival missions:  to protect and restore the Chesapeake Bay and to support mental health awareness.   

The Green Team had volunteers at the recycling and composting stations to educate us on the festival’s no-waste efforts.  Single-use plastic water bottles weren’t sold, as attendees were encouraged to bring a reusable bottle to refill at the provided water stations. Oyster shells were even recycled.  Non-profit organizations were set up to share information and educate us all throughout the weekend.   It was evident that we were going to leave a positive impact on the park, something that is rarely achieved at a music festival. 

At the end of the weekend, we all felt like we were blessed to be part of something from the very beginning.  The groundwork has been laid, and it’s easy to see that Baygrass is going to evolve into a unique and special festival. 

Annapolis Baygrass Music Festival 2023 | Mallory Petty

The Green Team at Annapolis Baygrass Music Festival 2023 | Mallory Petty

Annapolis Baygrass Music Festival 2023 | Festy GoNuts

Mimi Naja, Jay Cobb Anderson and Kellen Asebroeck at the Workshop Pavillion at Annapolis Baygrass Music Festival 2023 | Festy GoNuts

The Adventure: Bridges, Boats and the Bay


On our way to Baygrass, we drove over the Chesapeake Bay Bridge.  An impressive 4.5-mile-long steel structure that connects the Eastern and Western shores of the Bay, it can be simultaneously daunting and inspiring.  

As you near the end of the bridge, you can catch your first glimpse of the sandy beach at Sandy Point State Park.  Our excitement was building.  If anything, the views from the festival were going to be outstanding. 

If you haven’t been to Maryland before, it should be on your bucket list. It might be one of the smallest states in the country, but it offers some of the most varied landscapes.  You’ll find iconic cities, charming small towns, beautiful beaches, dramatic coastlines, tree-lined mountains and trails, and rolling countrysides.  

We arrived a couple of days early to enjoy downtown Annapolis, Maryland.   You can easily entertain yourself for days walking through this historic town, stopping to enjoy a delicious meal or a rooftop cocktail.   A boat tour was the perfect way to see the city from a different view and the easiest way to get out into the Bay.  We all enjoyed an afternoon stroll through the Naval Academy, especially visiting the chapel and crypt

Annapolis Baygrass Music Festival 2023 | Festy GoNuts

The Chesapeake Bay Bridge | Annapolis Baygrass Music Festival 2023 | Festy GoNuts

While in Maryland, be sure to take your taste buds on an adventure as well. Indulge in the seafood; after all, it’s what Maryland is known for most.   Pick steamed blue crabs covered in Old Bay. Slurp down raw oysters. Satisfy your sweet tooth with a Maryland snowball, and don’t be afraid to get the marshmallow cream topping.  And if you head down the Eastern Shore, be sure to order an Orange Crush at the bar. 

Destination festivals allow you to travel and see music, so it’s like a two-for-one vacation.  Annapolis Baygrass Festival partnered with several local hotels and a nearby KOA campground to get discounts for festival attendees.  Shuttles were available to take you to and from the festival grounds, so you didn’t need to worry about driving (or renting a car).  If you’re coming by plane, BWI (Baltimore-Washington International Airport) is only about 30 minutes away. 

If you’re not coming from out of town, just spending time at Sandy Point State Park can be an adventure.  With over 700 acres to explore, you’ll want to arrive before the festival to take it all in.  The park boasts a mile-long beach, perfect for fishing, crabbing and swimming.  Bring your boat and dock it before the festival.  Explore the bay in a kayak, or try windsurfing if you’re feeling adventurous. 

No matter how far you travel, an adventure can be made simply by discovering new bands, meeting new friends and being part of the Baygrass community.   

Annapolis Maryland moonrise | Festy GoNuts

Moonrise over downtown Annapolis, MD | Festy GoNuts


The inaugural Annapolis Baygrass Music Festival wrapped up on a beautiful Sunday evening, a powerful moon rising into the starlit sky over the Chesapeake Bay. 

We danced with partners and strangers, smiling while singing “How Sweet It Is.”  It can be no coincidence that this song made appearances on both days of this festival, closing out amazing sets of music. 

Everyone at Baygrass, from artists to fans, volunteers to founders, felt just how sweet this was.  Perhaps that encore was a nod to all of us who took a chance on a first-year festival. We were all sweetly rewarded with being a part of something truly special. 

See you in 2024, Baygrassers.

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Annapolis Baygrass Music Festival 2023 | Festy GoNuts
Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Saturday Super-Jam with Railroad Earth, Yonder Mountain String Band | Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

Annapolis Baygrass Music Festival 2023 | Jay Strausser Visuals

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About The Author

Kelly Day

Kelly is pretty crazy about live music, camping, road trips and making lots of new friends. So, music festivals are basically the best thing in the world to her. She really wants Festy GoNuts to become a huge success so she can continue to drive around the country checking out live music, camping and making lots of new friends. Sounds like a plan.

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