Looking for laughs? Hosted by the Charm City Comedy Project since 2014, the Charm City Comedy Festival is a two-weekend-long celebration of comedy, showcasing solo stand-up comedians and improv and sketch groups from Baltimore and across the country. The festival also hosts workshops for budding comedians taught by professional teachers and performers. Held at Zissimos Bar, tickets are available for individual performances or as weekend passes.
The second race for the coveted Triple Crown takes place during the Preakness Stakes at the historic Pimlico Race Course in Baltimore. Preakness is known for its fancy hats and Black-Eyed Susan cocktails, but the main race isn’t the only attraction. Friday kicks off with the Black-Eyed Susan Stakes, one of Pimlico’s oldest stakes races, which, as it features exclusively fillies’ races, has become a women’s event. Since 2008, Preakness has also hosted the Budweiser InfieldFest, amping up the party atmosphere of the general-admission infield with well-known musical acts such as Lorde and The Chainsmokers.
The Sowebo (Southwest Baltimore) Arts and Music Festival takes place on the Sunday of Memorial Day weekend to truly kick off the summer festival season. The 35-year-old event in Hollins Market hosts local and visiting arts and crafts vendors to show off the community’s unique and vibrant arts scene. Musicians of many stripes perform throughout the day, and kids of all ages can participate in an interactive arts alley.
The free two-day Federal Hill Jazz & Blues Festival takes place in a scenic neighborhood with performances by amazing local jazz and blues bands. With over 80 food and craft vendors, plus special kid-friendly activities, it’s a great way to get outdoors and spend some time in the historic Federal Hill neighborhood in early June.
The largest Pride festival in the state, and one of the oldest in the country, Baltimore Pride is a vibrant, inclusive celebration. Run by the GLCCB (Gay, Lesbian, Bisexual and Transgender Community Center of Baltimore), Baltimore Pride kicks off with a massive parade on the Saturday of Pride Weekend, leading into a late-night block party. The Sunday festival takes place in Druid Hill Park with performers and family-friendly events. The whole thing runs on volunteers and donations, and the GLCCB uses all proceeds from the event to help 800 sexual and gender minority people each month, so don’t miss out.
HONFest in Hampden is all about the warmth and charm of Baltimore’s working-class women, captured in bright pink, cats-eye glasses, beehive hairdos, and feather boas. What started as a “Baltimore’s Best Hon” contest by Cafe Hon at the 1994 Hampden Summer Fair has turned into a thing all its own, with over 100 vendors, art exhibitions, three stages of entertainment, and, of course, the Baltimore’s Best Hon contest. So grab some glasses and a boa to join in this essential Charm City festival.
Called the world’s largest and best crab fest, the Chesapeake Crab & Beer Festival is an all-you-care-to-taste crab extravaganza at Rash Field in the Inner Harbor. Enjoy tons of fresh, seasoned crab—six at a time per person—with your choice of over 50 beer and wine varieties, plus other food options. There are plenty of tables, chairs, and tents set out for this jam-packed event, along with live music. Grab a ticket before they’re gone!
As the birthplace of “The Star-Spangled Banner,” Baltimore’s Independence Day is definitely one of the top summer events. Baltimore’s Ports America Chesapeake Fourth of July Celebration features live music from the U.S. Navy Jazz Ensemble and a fireworks display over the Inner Harbor. The Top of the World Observation Level hosts a Picnic at the Top, where guests can see the fireworks from high above and enjoy food, drinks, and activities. During the day, make sure to visit Fort McHenry to honor the country’s history and enjoy fife and drum performances, cannon and musket demonstrations, and a reading of the Declaration of Independence.
Artscape is the largest free arts festival in the United States, with over 150 artists showcasing their work through multiple neighborhoods. With participants from local artists to establishments like the Baltimore Symphony Orchestra and National Aquarium, it covers pretty much everything under the arts umbrella – arts and crafts, sculptures and outdoor installations, interactive exhibitions, performing arts, film, experimental music, comedy and more. The festival also serves 100% local food and beer.
Baltimore is host to multiple outdoor film festivals from June-August in some of the most popular neighborhoods. Some highlights include the Cinema al Fresco – Open Air Film Festival in Little Italy, Flicks From the Hill at the American Visionary Arts Museum, and Films on the Pier in Fells Point. These free festivals make a Saturday night at the movies all the more memorable as you enjoy the summer night air.