Baltimore Seafood Festival
Sept. 15. The Canton Waterfront Park, 3001 Boston Street. Wed-Sun Noon-7 p.m. Free-$105. We take seafood pretty seriously in the Land of Pleasant Living, and this end-of-summer celebration is a chance for locals and visitors alike to feast on some of the best blue crabs, crab soup, crab cakes, and, of course, oysters that Maryland has to offer. At this fifth annual festival at Canton Waterfront Park, sip on refreshing cocktails, listen to live music, and honor the bounties of the bay from noon until sundown.

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Charles Street 12
Sept. 1. The Shops at Kenilworth, Towson. 7:30 a.m. $80-90. The idea of running 12 miles in Baltimore’s late-summer heat is nothing short of intimidating, but this annual trek from Towson to Locust Point features city views (and hopefully a harbor breeze) worth running for. Lace up your sneakers and join thousands to jog down Charles Street from the Shops at Kenilworth, to the Inner Harbor, and around to Under Armour’s waterfront headquarters. After crossing the finish line, stick around for post-race festivities, including free beer, snacks, and live music.

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Baltimore Comedy Festival
Sept. 1-3. Multiple Locations. 7 p.m.-11 p.m. Free-$10. For the second year, this comedy extravaganza will bring free standup performances, panel discussions, and podcast recordings to more than 20 venues across the Baltimore region. With an opening ceremony at Station North’s Motor House, the festival will be filled with side-splitting showcases by more than 100 comedians, including many from Charm City’s own flourishing comedy scene.

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Hateful Things
Sept. 1-Oct. 14. Reginald F. Lewis Museum, 830 E. Pratt St. Wed-Sun 10 a.m.-5 p.m. Free-$8. In this highly anticipated special exhibition at the Reginald F. Lewis Museum, controversial memorabilia such as banks, posters, and tobacco tins featuring racist caricatures will be displayed as examples of the country’s segregated past. View materials from the late-19th century to the present that represent the lasting effects of the Jim Crow era, and, on September 22, participate in a discussion hosted by the Johns Hopkins University Center for Africana Studies about the history of objects used to negatively stereotype African Americans.

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Little Italy Madonnari Arts Festival
Sept. 7-10. Multiple Locations. Free. During one of Little Italy’s fan-favorite traditions, master street-painting artists from around the world will color the city to reflect this year’s festival theme: respect. Watch as street artists fill the neighborhood’s historic sidewalks with chalk masterpieces and create a colorful homage to Baltimore’s cultural diversity.

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Hampdenfest
Sept. 8. W 36th St. 11 a.m.-7 p.m. Free. For one day only, Hampden’s can’t-miss block party returns with its annual celebration of one of the city’s most quintessential Bawlmer neighborhoods. Indulge in local food and drink, browse regional arts and crafts vendors, cheer on contestants in the Dangerously Delicious pie-eating contest, and rock out to three stages boasting hometown bands such as F City and Raindeer. Just be sure not to miss the iconic Toilet Races as porcelain flies down Chestnut Avenue.

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Trillectro Music Festival
Sept. 22. Merriweather Post Pavilion, 10475 Little Patuxent Parkway, Columbia. Noon. $79-199. Since its inaugural festival seven years ago in Washington, D.C., this hip-hop and electronic music festival has found a new home at the Merriweather Post Pavilion and grown into a can’t-miss concert that draws big-name acts and thousands of fans to Columbia every fall. At the end of the month, hear a killer lineup of artists including R&B star SZA, rapper 2 Chainz, internationally renowned DJ Carnage, and even a set by local performers curated by Lawrence Burney of Baltimore arts publication True Laurels.

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Pigtown Festival
Sept. 22. 700-900 blocks of Washington Boulevard. Noon-7:00 p.m. Free. One of Baltimore’s most anticipated races of the year is finally here—no, not the Preakness Stakes—it’s “Squeakness,” aka Pigtown’s annual contest that sends piglets running around a ring on Washington Boulevard. Aside from this crowd-favorite tradition, the Southwest Baltimore festival boasts plenty of family-friendly fun, including live music, local food trucks, and an arts and crafts zone.

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Baltimore Comic-Con
Sept. 28-30. The Baltimore Convention Center, 1 W Pratt St. Fri-Sun Noon-7:00 p.m. $25-500. For one weekend, the Baltimore Convention Center will transform into a comic book-lover’s paradise, complete with a costume contest, tons of comic books to peruse or purchase, and the chance to rub elbows with fellow nerds and famous cartoonists alike. Come decked out as your favorite superhero or villain during this 19th annual festival and take advantage of art exhibits, panels, and autograph sessions. Stick around for the chance to meet Maryland-born graphic novelist Frank Miller, the creative force behind the late-era Batman comics, or actor Zachary Levi, the future Shazam and voice of Flynn Rider in Tangled.

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Baltimore Book Festival
Sept. 28-30. Baltimore Inner Harbor. Fri-Sun 11 a.m.-7 p.m. Free. Ten years after the release of her eighth book, The Glen Rock Book of the Dead, local author Marion Winik realized she had enough material to fill a sequel. (Since the first book’s publication, her mother, the family goldfish, and one of her favorite musicians, Lou Reed, had died.) With the same candid and often humorous writing style she fine-tuned through her years as an All Things Considered commentator, Winik memorializes the departed in short essays that evoke a tender sense of connection in readers. During the Baltimore Book Festival on September 28-30, she will debut The Baltimore Book of the Dead with a reading at the Inner Harbor Stage on Friday ahead of the official release on October 9. “For me, it’s important to find material that is challenging and scary to write about because that usually means that you’re onto something interesting.”

 EAT

September 3: La Cuchara’s Tomatina Battle & Food Festival

La Cuchara, 3600 Clipper Mill Road, Ste. 125, 1-6 p.m., $15 entry fee for tomato fight.

It’s been two years since La Cuchara first brought the Spanish and French flavors of the Basque region to Woodberry—gracing us with everything from pintxos and prosecco pairings to charred meats and calcots (grilled green onions native to the Catalan). Now, the restaurant is continuing that authenticity by putting its own spin on La Tomatina—an annual end-of-summer festival held in Buñol, Spain in which revelers pack the streets to partake in a massive tomato fight. This weekend, throw on a pair of goggles and pelt the ripe fruits at friends and neighbors in La Cuchara’s inaugural tomato battle benefitting local youth development program Baltimore SquashWise. Of course, no party is complete without eats and drinks, and there will be plenty of options from local favorites Blue Pit BBQ, Ekiben, The Local Oyster, and Union Craft Brewing. Plus, D.C.-based folk rocker Tomas Pagan Motta will be on hand to provide the soundtrack for the afternoon.

 DRINK

September 2: Labor Day Par-tay at Hysteria Brewing Company

Hysteria Brewing Company, 9570 Berger Road, Columbia, 11 a.m.-11 p.m., Free

Hysteria Brewing got off to a good start with a grand opening soiree over Fourth of July weekend, and now it’s closing out the summer in a similar fashion—with a full-blown Labor Day bash. Not only will the party toast the debut of the brewery’s new experimental series (and a few fresh batches), but it will also celebrate the brand-new 1624 Corn Whiskey from next-door neighbors Lost Ark Distilling Company. Head to the steampunk-themed taproom to explore whiskey and beer collaborations, sip Hysteria signatures (think the Idle Hands Sour Cherry Tripel, Yellow Sudmarine Hefeweizen, and Trash Panda IPA), and sample from limited-release firkins. All the while, line your stomach with food truck fare from River House Pizza Company and Anegada Delights Caribbean Cuisine. The all-day event will also feature unplugged sets from local duo Acoustic Wheelhouse and Americana jams from Columbia rockers Artistic Differences.

 SEE

September 2: 10th Annual DIY Fest

St. John’s Church, 2640 St. Paul St., 12-6 p.m., Free

Nowadays it seems like everything taps into the DIY trend. But we can’t forget that Baltimore DIY Fest was teaching locals how to take charge of tasks long before Pinterest came around. Now in its 10th year, the hands-on festival returns to St. John’s Church with upward of 15 free workshops exploring everything from vegan cooking to independent filmmaking. Learn how to plant fruit trees with The Baltimore Orchard Project, paint selfie portraits with local artist Katia Baskina, repair a bike tire with Baltimore Bicycle Works, make your own ’zine with local storyteller A. Jarrell Hayes, and more. In keeping with the event’s innovative spirit, there will also be scratch-made goods and gifts for sale by more than 25 area artisans. Following the festival, head to Baltimore Free Farm in Hampden to dance the night away at an after-party featuring the sounds of local surf rockers The Flying Faders and new-wave group PLRLS.

 HEAR

September 1: Friends Records Presents: Wing Dam, Spaceface, Natural Velvet

Current Space, 421 N. Howard St., 7-11 p.m., $10

There’s just something about the energy of a show under the stars. As the end of summer officially nears, soak up every second at this outdoor performance in the parking lot of downtown arts venue Current Space—where Friends Records label mates Spaceface, Wing Dam, and Natural Velvet will take the stage. The show doubles as a release party for Spaceface’s new LP “Sun Kids,” a model showcase of the band’s psychedelic style led by the dreamy vocals of Flaming Lips guitarist Jake Ingalls. Local post-punk rockers Natural Velvet—with their powerful lyrics and thundering sound—are also not to be missed, along with a closing set from alt-rockers Wing Dam, who return to Charm City after touring the country this past year. With plenty of rosé, cocktails, and $2 cans of Natty Boh at the bar, we can’t think of a better way to say goodbye to summer.

 DO

September 2: Charles Street 12

The Shops at Kenilworth, 800 Kenilworth Drive, Towson, 7:30 a.m., $85-90

Though to some it might seem sacrilegious to rise at the crack of dawn on a Saturday (especially during a three-day weekend), hundreds of runners will be up bright and early this weekend for this annual race down historic Charles Street. This year, the run returns with a new route that descends into Under Armour’s global headquarters at Tide Point Waterfront Park in South Baltimore. Curate the perfect playlist and lace up your running shoes to hit the pavement while taking in some of the city’s most beautiful sights along the way. Afterward, treat yourself to snacks from Upslide Down Dave and Wolo food trucks, as well as local libations from the likes of Charm City Meadworks and Key Brewing at Under Armour’s post-race party.