Here are my totally opinionated picks on what to catch live in May.

What's Playing May
Image courtesy of Jarflys

May 4: Jarflys at Metropolitan

Local artist-publisher-musician-creative champion Jimi HaHa brings some of the area’s top musicians together as Jarflys, playing May 4 at Metropolitan Kitchen and Lounge. Expect witty lyrics and danceable grooves from the band, which always draw a crowd.

What's Playing May
Image courtesy of First Sunday Arts Festival

May 5: First Sunday Arts Festival kickoff day

The summer’s most popular street festival kicks off on Sunday, May 5, taking over the first three blocks of West Street from 11 am to 5 pm. Check out the next generation of musicians from the Priddy Music Academy in Whitmore Park; blues by Reggie Morris Band at Weisman Park at 2 pm; and retro rock and swing from Fast Eddie and the Slowpokes at 3 pm at the Stan & Joe’s performance area.

What's Playing May
Image courtesy of Rams Head On Stage

May 11, 13, 23, 25: Singer-Songwriters at Rams Head On Stage.

If you love singer-songwriters, Rams Head has you covered this month. Americana trailblazer Alejandro Escovedo plays a special matinee show on Saturday, May 11, followed by English legend Richard Thompson playing solo acoustic two nights later. (The latter was sold out at press time but there’s a waiting list.) Virginia native David Lowery started off making catchy, quirky music in the 1980s with cult band Camper Van Beethoven, followed by indie chart hits in the 1990s with Cracker. The latter plays Rams Head, and you can always expect the unexpected, including deep digs into their back catalog if you’re lucky. Country music legend Rodney Crowell completes the trifecta with an all-ages matinee on Saturday, May 25.

What's Playing May
Image courtesy of Maryland Hall

May 26: The Temptations at Maryland Hall

The Motown pioneers’ story is drawing raves in their musical, Ain’t Too Proud to Beg, which just opened on Broadway after debuting at the Kennedy Center. But you can catch the real thing at Maryland Hall, where the band led by founder Otis Williams will showcase a slew of pop classics including “Just My Imagination,” “Papa Was a Rolling Stone” and of course, “My Girl.”

Susan Moynihan

Susan spent her teenage years in Annapolis, when her parents settled here post-Navy career. After graduating from the University of Maryland, she set her sights on New York City, equally entranced by magazines and rock and roll. A chance trip to the Caribbean led her to the discovery of travel writing, and she spent the next 15 years as a travel editor, exploring the world from home bases in NYC and Florida. In 2013, she left publishing to start a travel planning company, The Honeymoonist, while continuing to write for national magazines. She relocated to Annapolis in 2018, and is thrilled to get to rediscover the area she’s always called home. When she’s not out scouting, Susan is playing her ukulele, chasing her schnoodle Ira, or volunteering with Annapolis Green.