Navigating the Annapolis Songwriter Festival  

The second annual Annapolis Songwriter Festival rolls into town for four days beginning Sept. 14, offering a great chance to experience live music without traveling to Nashville, Key West, or New Orleans. But with over 100 artists and almost 20 venues, it can be overwhelming to navigate the lineup.   

The festival is modeled after the Key West Music Festival, where singer-songwriters perform and tell the stories behind their music. Large venues such as Annapolis City Dock, Maryland Hall, and Ram’s Head offer maximum spaces for the big names. Smaller spaces like Metropolitan, King of France, and 49 West allow for a more intimate musical experience. However you choose to work the festival, it’s an excellent opportunity to pack in multiple shows at multiple venues—and hear from a wide range of artists on what inspires their music and journey.   

For a stress-free and meaningful experience, here are a few tips:  

1. Is this Date Night or Girls’ Night Out?   Ever wish you could relive (or redo) your bachelorette in Nashville? Or say that you and your honey always listened to live music before kids came along? The Annapolis Songwriters Festival experience caters to all of us. Venues such as Ram’s Head on Stage, Annapolis City Dock, and Maryland Hall have tickets left for Blondie, Michelle Branch, and others, allowing you to get a group together and prove that you haven’t forgotten the lyrics despite all these years. But if you’re looking for a unique take on romance, Annapolis’ most popular date night spots have great acts performing during dinner hours.   

2. Are You Raising the Next Taylor Swift?   Are you trying to cultivate your child’s musical talent? Many venues have artists performing during daytime hours. Ram’s Head, Capitol Hotel, 49 West, and others will have music starting as early as 11 am, while other family-friendly restaurants (Metropolitan, Graduate Hotel Bar) will have artists starting during the dinner hour and welcome younger audiences.   

3. Who Needs Tickets?  One of this festival’s most attractive qualities is that most events are entirely free. And since many acts take place in restaurants, you can enjoy a great dinner with entertainment as the cherry on top. King of France and Stan and Joe’s offer an excellent lineup for happy hour, allowing you to continue your venue crawl to a restaurant with options for food beyond pub fare. On Saturday evening, you’ll want a reservation for one of Main Street’s Dinner Under the Stars performances. But otherwise, just show up.   

4. Remember: Google Before You Go. The festival brings in musicians whose careers have influenced the music industry in myriad and unexpected ways. For instance, Tim McGraw and Rascal Flatts both reached the Billboard No. 1 spot with songs written by Jeffrey Steele, who performs a solo show on Ram’s Head patio Thursday. Artist K. Michelle, who plays at Ram’s Head on Stage Saturday, was on the VH1 show “Love and Hip Hop,” and the music of Striking Matches, who are part of a two-hour musical Watermark cruise on the Severn River Friday, was featured regularly on the television show “Nashville.” These artists all have stories to tell and great melodies to groove to, and a quick bit of research will enhance the experience.

For showtimes, all venues, and much more, visit www.annapolissongwritersfestival.com