Annapolis Baygrass Arrives as a Premiere Destination Festival

The 3rd Annual Annapolis Baygrass Music Festival took place at Sandy Point State Park in Annapolis, MD, September 20 & 21, 2025. Headliners Greensky Bluegrass, Molly Tuttle, Kitchen Dwellers, Railroad Earth and The Travelin’ McCourys were joined by Artists-at-Large Holly Bowling and Kyle Tuttle, along with many others.

We love a good destination festival. (Fun fact – Festy GoNuts arose out of our love for travel and an early attempt at a travel blog under the name Jelly GoNuts)

If you follow along in our adventures, you’ve read about (or joined us at) multiple festivals in Mexico, musical excursions to Iceland, and sailing adventures through the Caribbean.

As amazing as any music festival can be, there is just something even more special about taking that format outside the norm and experiencing new cultures, scenes, food, drink, and people.

Typically, these destinations involve a location considered exotic or distant, which is why you may be scratching your head reading this, wondering how this applies to a festival in Maryland.

Well, keep reading…

Annapolis, Maryland: A unique destination with its own culture

Traveling to Annapolis is a trip to a destination rich in history, culture, and cuisine. 

First off, there is the amazing downtown, home to the Maryland State capital and the US Naval Academy. This place holds historical significance and has played an important role in the ongoing saga of this country.

Annapolis’s culture is deeply intertwined with the water, as the city is shaped by its surrounding waterways, where you can always find kayakers, paddleboarders, and fisherfolk.  Boating, in its various forms, is a central pastime, from morning fishing excursions to relaxing sunset sails. 

Then there is the food.

Annapolis is in a region of the Chesapeake with a unique flavor, drawing from the neighboring Eastern Shore region, with a flair and style of its own.

Chesapeake food and culture are centered around the Maryland Blue Crab. We say culture, because crabs are more than a meal – they can be a way of life. For many, there is simply no other way to celebrate than with a crab feast. But if sitting around picking crabs all day isn’t for you, there are also crab balls, crab soup, crab Imperial, and the infamous Maryland Crab Cake.

Add in steamed shrimp, raw and grilled oysters, catfish, and Rockfish, and you’re starting to get the picture. Now cover that picture in Old Bay – the Baltimore-born seasoning that is a beloved cultural icon and a defining part of Maryland’s identity – and you’ve got it!

The beauty of Annapolis is that the cuisine is equally enjoyed in casual, paper-covered crab feasts and in upscale waterfront restaurants. In Annapolis, you can be just as comfortable with a bucket of beers on a patio as you can be with a glass of champagne on a sailboat. Or better yet – an Orange Crush – the official State Cocktail of fresh-squeezed oranges, orange vodka, triple-sec, and Sprite.

All of this adds up to a compelling cultural destination worth visiting, one we have returned to over and over.

Annapolis Baygrass Music Festival embraces the local culture of Annapolis and the Chesapeake.

When Baygrass first hit the scene, Festy GoNuts was elated with the way the festival embraced and celebrated the local culture.

Annapolis Baygrass Music Festival is dedicated to protecting and restoring the Chesapeake Bay, where it takes place. In addition to its environmental focus, Baygrass partners with local organizations to raise mental health awareness and offer wellness resources and tools to the public.

As soon as one sets foot onto the beautiful festival grounds of Baygrass, these missions and the local influence are immediately evident.

The Bay Guardian Village hosts the local non-profit organizations that help fulfill these goals, and the importance of these missions to the Baygrassers in attendance was evident in constant engagement throughout the weekend.

Local food vendors proudly serve dishes with regional flair. Freshly shucked raw and grilled oysters are a popular local delicacy, attracting a constant line of fans.

For those who opted for the VIP Upgrade (totally worth it, in our opinion), a half-dozen oysters are included each day, and the chef-prepared daily hot meals are all locally sourced and influenced.

Craft breweries pour a selection of local brews, including some created specifically for Baygrass. And, yes, there are Orange Crushes on hand!

The festival’s home of Sandy Point State Park lives up to its name with a beautiful stretch of sandy beach. An iconic view of the Chesapeake Bay Bridge serves as a constant backdrop for the festivities. Kids play in the surf, Baygrassers enjoy a myriad of water activities just off the shore.

On the beach, people take a break from dancing to play a quick game of cornhole, and ring-hook can be found on the many convenient picnic tables of the Beer Garden – a popular game inspired by sailing and played in many local bars throughout the region.

Just beyond the beach, there are dozens of beautiful sailboats criss-crossing the horizon from sunrise to glorious sunset.

The result is the feel of a secret destination, and a step into another world at Baygrass.

Baygrass as part of a late-summer vacation

From over 40 states, fans arrived in the region for the 3rd Annual Baygrass Music Festival. Those with time on their schedules had a ton of itineraries and activities available surrounding the festival.

One could easily spend a week in Annapolis, exploring the town, going on local hikes, hopping on a sunset cruise, and eating crabs, shrimp, and oysters.  Or, visit one of the other amazing nearby towns. Baltimore, Washington, D.C., and Philadelphia are all within a short drive and are definitely worth a visit.

Festy GoNuts opted to return to some of our roots and visit Ocean City, MD, for the week prior to the fest. We visited Harborside Bar & Grill, the home of the Orange Crush. We played skeeball on the boardwalk. We picked a dozen steamed crabs, and we drank a bucket of beers.

The point is, as festival destinations go, the options for exploration around Baygrass are limitless.

And once you arrive at Baygrass, the cultural immersion continues throughout your stay, as you reside alongside the local community. The many Baygrass partner hotels are surrounded by local bars and restaurants.  Many of the hotels and AirBnB options are in the heart of downtown Annapolis, where you can stroll the town and enjoy breakfast before heading to the festival.

At Festy GoNuts, we always push the culture and adventure around music festivals.  We urge visitors to extend their trips whenever they can and create greater experiences, with longer-lasting memories. No fest offers this opportunity more than Baygrass. 

Now on to the music…

The Music Never Stopped…

As with our other destination festival excursions, the music is what gets us there to begin with, opening us up to new and exciting adventures. Baygrass is no different – the lineup for this festival was one of (if not the) best festival rosters of the year.

We got the party started early at the Official Kick-Off Party at Maryland Hall in downtown Annapolis, with local trio (and 2023 Baygrassers) Wicked Sycamore, and the up-and-coming Fitzkee Brothers. It was an amazing start to the weekend, and the local music involvement of Baygrass was evident when seeing the ladies of Wicked Sycamore dancing all weekend at the festival, while the Fitzkee Brothers transitioned to their role as stagehands.

Saturday’s lineup was incredible, right out of the gates. We began with a tearful National Anthem sung by Jill Simmons of Brown Eyed Women, who performed at last year’s Baygrass. All in attendance turned to admire the American Flag as it waved in all its glory over the glistening waters of the Chesapeake. It was a beautiful moment, and signalled the start of a beautiful weekend.

Local artists and Official Baygrass House Band, Geraldine, got things going as they have every year, sending us into the festivities with smiles all around. Elliott Peck & Friends followed with one of the most memorable performances of the weekend, and Sam Grisman Project continued the vibes with new and classic bluegrass tunes that hit all the feels. Larry Keel – another returning Baygrasser – kicked things into high gear with Electric Larry Land, delivering a guitar-rocking shred-fest. The power trio of LaMP kept everyone on their feet, where they would remain for the rest of the evening.

Kitchen Dwellers made their second appearance at Baygrass, this time warming up for Greensky. They did more than warm things up – they brought the heat with an incredible set to remember. Greensky Bluegrass then topped things off with 2 killer sets on Saturday night – joined for their entirety by their unofficial (but sort of official) 6th member, artist-at-large Holly Bowling. (Baygrass knew what they were doing with this booking!) The other artists-at-large, Patrick Rainey and Kyle Tuttle, sat in on several tunes, as they had been doing all day, taking familiar songs to new heights.

Sunday saw Baygrassers all around hitting their stride – comfortable in their surroundings, settled in, glowing in the aftermath of a perfect day, and ready to do it again.

Local rising stars Pressing Strings were the perfect way to continue the previous day’s energy. The Last Revel carried the vibe and played a set that was talked about throughout the day. Then the legendary Travelin’ McCourys took the stage for their first of two appearances. In this slot, they delivered originals, classics, and some surprising covers.

Kyle Hollingsworth of String Cheese Incident took the stage next. The Baltimore-native also collaborated with Pickett Brewing for his own unique blend that was poured up in the VIP Village. Kyle and his band threw down one of the most high-energy sets that this festival has seen in its 3 years. A tough act to follow, but a challenge that The Travelin’ McCourys had no problem facing with their epic Grateful Ball set.

Then came one of the highlights not only of this festival, but of the summer. Molly Tuttle and her new band delivered for her faithfully devoted fans and her brand new ones alike. It was purely crafted entertainment at its finest – a degree of musicianship, energy, and fun that wowed every person at Sandy Point State Park.

Railroad Earth had the pleasure of closing out the entire fest and did it as only they could. Every single person at the festival sang together, arms in the air, smiles, hugs, and tears throughout the crowd, as Railroad put a bow on the gift of a simply magical weekend.

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But wait. There’s more…

We’ve been covering Baygrass since the beginning, and urge you to revisit those past reviews to learn all about the other amazing offerings of this uniquely brilliant music festival.

👉 Annapolis Baygrass Festival 2024 Review: A Homecoming Celebration
👉 Inaugural Annapolis Baygrass Festival Already Feels Like Home: REVIEW

Learn about all the workshops that are such an amazing part of this fest, where you can learn to shuck oysters, fry catfish, or listen to artists discuss their craft.  Anders Beck hosted a workshop on his unique instrument and discussed fooling Greensky into thinking his dobro sounds are originating from Holly’s keyboards. Kyle Tuttle held the crowd with stories about playing with Jeff Austin. All in attendance joined for a toast with the festival founders.

Read about Yoga on the beach, and the activities and games for all ages, especially the amazing KidZone. Learn about the amazing Sober Space offered by The VA Way, and the many mental wellness discussions and panels.

We could go on and on, but really, you just need to experience this.

Annapolis Baygrass is a destination worth traveling for.

With amazing and diverse local activities surrounding the festival, a ton of convenient lodging options, a shuttle that takes you to and from the festival, a location that rivals any music festival in this country, and a lineup that continues to be amongst the best of the year, Annapolis Baygrass is a destination festival that should be on everyone’s radar.

The culture and cuisine of the region give this destination an exotic feel rivaling any in the country, the world, for that matter.

All of that makes Annapolis Baygrass one of the best destination festivals around, so start planning your next vacation!  (Live in Maryland or nearby?  Lucky you! See you there!)

Mark your calendars and start planning for Baygrass 2026 – September 19 & 20!