Chalk It Up – Madoranni Festival
Sept. 6-8. 11 a.m.-10 p.m.. Little Italy, Baltimore. Free. After Michael Kirby discovered his talent for street art as a teenage spray-painter, the Parkside native went on to create thousands of Renaissance chalk paintings and become the first American artist to achieve the title of “master street painter” in major European festivals. Now the founder of local studio Murals of Baltimore, Kirby has seen the Little Italy Baltimore Madonnari Arts Festival grow into a much-anticipated affair that draws thousands of onlookers to the neighborhood to watch local and international artists create pavement masterpieces. Kirby says the most important part of the festival (September 6-8) is that it brings both new and familiar faces to Baltimore. “People will visit on Friday to see what the artists are drawing and then come back again on Sunday to see the finished piece,” Kirby says. “Every day you come back, you see and experience something new.”—KP

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Locust Point Festival
Sept. 7. 11 a.m.-6 p.m.. Latrobe Park. Free. This South Baltimore neighborhood is known for being a mix of the old and the new, with some of the city’s oldest rowhomes mere blocks away from luxury high-rises and high-tech office spaces. So it’s no surprise that this annual festival at Latrobe Park will have tons of food and entertainment for residents of all ages, including delectable eats from City Limits, Hull St. Blues, and HarborQue, a kids zone packed with activities, a crush station, and live music by local band The Wafflers. Don’t miss the chance to give back to neighborhood projects through this family-friendly event.

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Baltimore Seafood Festival
Sept. 14. 12-7 p.m.. Canton Waterfront Park. Free-$100. What better way to honor Baltimore’s undoubted love for seafood than a full-blown festival with crustaceans as far as the eye can see? Head to Canton Waterfront Park for this sixth annual extravaganza as local seafood spots, including favorites like Jimmy’s Famous Seafood, Mason’s Famous Lobster Rolls, Nick’s Fish House, and The Local Oyster, serve up crab cakes, shrimp salad, oysters, and steamed crabs. Indulge in the only large-scale seafood festival in Baltimore City and spend the day trying new drinks, listening to live music, and taking in a cooking demonstration.

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Charm City Night Market
Sept. 21. 3-11 p.m. 200 Park Ave. & 100 N Charles St.. Prices vary. During the inaugural Charm City Night Market last fall, more than 12,000 people visited this one-day festival to sample authentic Asian-American eats, peruse locally made wares, and take pictures under the illuminated lantern walk. This month, the Park Avenue block party will make its much-anticipated return with 70 vendors, tons of entertainment on the festival’s outdoor stage, and a true showcase of the booming popularity of Asian cuisine in Baltimore. Be on the lookout for upcoming details about how a permanent revival of Baltimore’s Chinatown is on the horizon, thanks to efforts from the Chinatown Collective and Park Avenue Partners.

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Hampdenfest
Sept. 21. 11 a.m.-7 p.m.. 36th St., Hampden. Free. Nothing describes Hampden quite like the neighborhood’s much-anticipated toilet bowl race down Chestnut Avenue. Cheer on your favorite high-speed seat and then spend the rest of this day-long festival jamming to live music by more than 20 local bands, sipping on brews from The Brewer’s Art and Union Craft Brewing, shopping along The Avenue, and taking in the sights and sounds of this quintessentially Baltimore neighborhood.

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Pigtown Festival
Sept. 21. 12-7 p.m.. Pigtown Main St.. Free. The historic Pigtown annual neighborhood celebration will have you squealing with joy for the 18th year in a row. This fan-favorite event has all the key ingredients for a great festival experience: local food, craft beer, arts and crafts vendors, and kids’ activities. Not to mention live music from Ursula Ricks Project and The Scotch Bonnets. Oh, and did we mention the live pig races?

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Trash Wheel Fan Fest
Sept. 21. 7-10 p.m.. Peabody Heights Brewery, 401 E. 30th St.. $30-40. Although the Trash Wheel family has gained a national following, we know that the truest fans of these lovable garbage-suckers are right here in Charm City. Celebrate these solar-powered trash receptors with unlimited Peabody Heights brews, performance pieces and songs inspired by the trash wheels, and even a make-your-own fan art station to commemorate the trash-tastic evening.

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Charm City Run 20 Miler
Sept. 22. 8 a.m.-2 p.m.. The Northern Central Trail, Freeland. $55-60. Whether you’re preparing for a fall marathon or just need an excuse to get some early-morning pep in your step, sign up for this abbreviated run at the Northern Central Railroad Trail. This popular (but tough) 20-mile race will take runners from Hunt Valley to the Mason-Dixon Line. If you need extra motivation for this long-winded race, think about the cash prizes waiting for the top three male and female runners at the finish line.

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Maritime Magic
Sept. 27. 7p.m.. Frederick Douglass-Isaac Myers Maritime Park, 1417 Thames St.. $120-2,500. A good time for a good cause——what could be better than that? To attend one of the most anticipated fundraisers of the year, head to Frederick Douglass-Isaac Myers Maritime Park and enjoy unlimited bites and drinks from local vendors, a silent auction, and incredible live music by renowned New Orleans-based funk and jazz jam band Galactic. This jam-packed benefit will directly support the Living Classroom Foundation’s education, job-training, health and wellness, and violence prevention programs.

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Bmore Historic
Sept. 27. 8 a.m.-4 p.m.. Baltimore Museum of Industry, 1415 Key Hwy. $10-25. Calling all history buffs and die-hard Charm City lovers: This annual unconference (AKA participant-led meeting) will delve into everything you’ve ever wondered about the history of Charm City and its preservation. This Baltimore Museum of Industry forum is open to the public and will allow visitors to connect with local historians and archivists to enrich their understanding of this great city.

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Five things to eat, drink, see, hear, and do with your Charm City weekend.

 EAT

Sept. 9-10: Baltimore Ukrainian Festival

St. Michael Ukrainian Catholic Church, 2401 Eastern Ave. 12-6 p.m. Free.

Baltimore is the home to one of the Mid-Atlantic’s largest Ukrainian community, and this weekend, there will be a celebration of that rich Eastern European heritage during this 42nd annual festival near Patterson Park. For two days, celebrate beneath the golden domes of the St. Michael church, with live music, folk dancing, arts and crafts, a Ukrainian beer garden, and a hefty dose of traditional cuisine, such as kielbasa, latkes, borscht soup, homemade breads, and, of course, sweet and savory pierogis. On Saturday, even watch in awe or test yourself during the much-loved, highly competitive pierogi-eating contest. 

 DRINK

Sept. 9: Mommies & Mimosas

Dovecote Cafe, 2501 Madison Ave. 12-4 p.m. $35.

When you become a new mom, it can be hard to get out and socialize, let alone find time to eat a warm meal. But this Saturday, thanks to the Mommy Up meet-up and Best of Baltimore-winner Dovecote Cafe, local mothers can gather together for a three-course brunch featuring fellow inspiring women. Over Dovecote’s home-cooked fare and a few rounds of much-needed fresh mimosas, you can network and talk about the joys and challenges of motherhood. Bring your babes or come solo, but biggest of all, sit back, relax, and soak up some you time.  

 SEE

Sept. 8-10: Little Italy Madonnari Arts Festival

Little Italy. Fri. 5-10 p.m., Sat.-Sun. 11 a.m.-10 p.m. Free.

Madonnari art is an age-old practice of street painting, still found commonly along the cobblestones of Italy and, for one weekend, alongside the byways of Baltimore’s Little Italy. This weekend, watch master Madonnari artists from around the world—and right here at home—set up shop in the heart of the Italian neighborhood, where they’ll create beautiful works of chalk art on the city streets. With a sunny forecast, things look brighter than last year’s rainy weather. Stroll the streets to listen to live music, indulge in carbs at neighborhoods enotecas, and kick things off early during a cabaret dinner on Thursday at Germano’s Piattini.

 HEAR

Sept. 8: Underground Dance Party

The Ottobar, 2549 N. Howard St. 9 p.m.-2 a.m. $6.

This month marks the 20th anniversary of Baltimore’s beloved Ottobar (see our September issue, on stands now, for more), and to ring in the two decades, the Remington rock club has brought back some of its old favorites. J. Roddy Walston recently performed a few rabblerousing sets, and later this month, Candy Machine and Roads to Space Travel will be perfomring a throwback combo, as both bands performed during the Ottobar’s first month downtown on Davis Street in September 1997. This weekend, the venue is also reviving its “Underground” dance party, featuring classic Brit-pop, indie, and new wave anthems on the ones and twos all night. Think James, Blur, Oasis, Daft Punk, Depeche Mode—with drink specials to boot. A regular favorite for the last 10 years, this former monthly ritual is sure to pack the house. We only have one request: “Age of Consent” by New Order. 

 DO

Sept. 9: Hampdenfest

The Avenue, W. 36th St. 11 a.m.-7 p.m. Free. 

There are few neighborhoods in the city more quintessentially-quirky Baltimore than that of Hampden. On Saturday, head north and celebrate the hons and Hampdenites of its eclectic avenue with an end-of-summer block party, full of fun for the whole family. As you wander 36th Street, dig into eats from local restaurants, including slices by Paulie Gee’s, shucks by The Local Oyster, scoops from The Charmery, and a pie-eating contest with Dangerously Delicious, and sip on local beer, including the special Brewer’s Art/Union Craft Hampdenfest collab, Hampden On Rye. With three stages for live music, you can catch more than 20 homegrown bands, such as Snakes, Wume, Raindeer, and the inimitable headliner, Bond St. District. Just don’t miss the annual toilet bowl races, as porcelain flies past the colorful rowhomes of Chestnut Avenue.