September is the prime time for festivals, and the Annapolis Baygrass Music Festival proves it.

Fourteen bands will perform progressive bluegrass, American roots and improvisational music Saturday and Sunday on the beach at Sandy Point State Park.

Headliners on the two stages are Greensky Bluegrass on Saturday and Molly Tuttle on Sunday.

The weekend kicks off from 7:30-11:30 p.m. Friday at Maryland Hall with a pre-festival party featuring music by Fitzkee Brothers and Wicked Sycamore, food trucks, beer and wine.

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Maryland-based acts include Pressing Strings of Annapolis, Geraldine from Ellicott City and Patrick Rainey of Baltimore.

Jordan Sokel, Nick Welker, and Justin Kruger perform as Pressing Strings. The Annapolis-based Trio will be at the Baygrass Festival on Sept. 21, 2025.
Jordan Sokel, Nick Welker, and Justin Kruger perform as Pressing Strings. The Annapolis-based Trio will be at the Baygrass Festival on Sunday. (Pressing Strings)

Pressing Strings’ appearance will come just days after the release of their new single, “Blood To Me.” The band describes it as a portrait of a touring musician’s growing family.

Food, games, workshops with the musicians and exhibits round out the weekend. A portion of the proceeds will go to nonprofits including Watershed Stewards Academy, Oyster Recovery Partnership and Alliance for the Chesapeake Bay.

The concert site opens at 10 a.m. both days. Adult general admission is $140 plus taxes and fees for a single day, $240 plus taxes and fees for both days. Discounts for children, VIP and shuttle passes are also available.

Admission to the Friday night opening party at Maryland Hall starts at $20, plus taxes and fees.

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Here are more great things to do in the week through Sept. 24.

Pittsburgh artists Lenka Clayton and Phillip Andrew Lewis submitted their work "Mixed Signals" for the "Lost at Sea (Ulysses)" at St. John's College.
Pittsburgh artists Lenka Clayton and Phillip Andrew Lewis submitted their work “Mixed Signals” for the “Lost at Sea (Ulysses)” at St. John’s College. (Myers Art Museum)

Trippy art

12:30-6:30 p.m. Thursday

Ten international artists offer their take on Homer’s classic road trip in “Lost at Sea (Ulysses)” at the Elizabeth Myers Mitchell Art Museum.

Though inspired by “Odyssey,” Lost at Sea gives the artists space to find new meaning in the hero’s tale of getting very, very lost on the way home from war.

Artists include Marcel Broodthaers, Luis Camnitzer, Lenka Clayton and Phillip Andrew Lewis, Rose Finn-Kelcey, Felix Gonzalez-Torres, Renée Green, Lonnie Holley, and Josef Strau, with music by Charles Moody and a poem by Alice Oswald.

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Clayton and Lewis will hold a workshop tied to their three works in the exhibit on Oct. 24.

The show runs through Dec. 7. The museum on the campus at St. John’s College is open Thursday–Friday, 12:30–6:30 p.m., and Saturday–Sunday, 10:30 a.m. to 6:30 p.m.

Admission is free.

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Let’s Stay Together

8 p.m. Friday

To many listeners, Al Green is classic soul.

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Famed for a staggering eight gold singles from 1971-75 — “Let’s Stay Together,” “Tired of Being Alone” and “Call Me” among them — Green brings his national tour to The Hall at Live! Casino and Hotel in Hanover.

The 11-time Grammy winner left pop music in 1976, moving to gospel when he became an ordained Baptist minister in Memphis.

Green, now 79, will be singing his greatest hits. Admission is $75-$309 plus taxes and fees.

Dance Dance Dance

7:30 p.m. Saturday

The Queer dance troupe BigKid Dance will premiere its contemporary dance-theater production, “If I Die Before the Revolution” at Maryland Hall.

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The Philadelphia-based company’s work is a fantasized eulogy and valediction for a group of queer people trying to survive in today’s increasingly hostile society, and their hope for an enduring legacy.

Admission is $35 to $45 plus taxes and fees.

Mangia!

10 a.m.-3 p.m. Sunday

The Sons and Daughters of Italy Annapolis Lodge will be serving up Italian specialty food at their Fall Festa.

Meatball and Italian sausage subs, pasta dishes, calamari, cookies, cakes and cannoli are on the menu. Live bands will play Italian music, and an array of vendors, makers and local authors will round out the day at the lodge on Ridgely Avenue.

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Admission is free, but food and other purchases are priced individually. Proceeds support local and national charities.

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Pan-Americana

3 p.m. Sunday

The Naptown Philharmonic Orchestra will kick off its season with classic pieces from the Americas.

“Music of the Americas: A Celebration of Life & Culture” features Cañas y Su Mariachi de Oro, a mariachi band from Wheaton. Aaron Copland’s Shaker Melodies, Amy Beach’s Bal Masque and “Tico Tico” arranged by Christian Vásquez round out the program.

Led by Jose Canas, the mariachi band will also perform during a free reception after the concert.

Tickets for the community orchestra’s afternoon concert at Maryland Hall are $25 plus taxes and fees. Student tickets are free.

Season finale

6-10 p.m. Wednesday

It’s a wrap for the 10th season of Dinner Under the Stars on West Street.

Restaurants set out tables and chairs, and there’s music and vendors.

Admission is free. The Annapolis-based funk band Souljourners is performing.