Five things to eat, drink, see, hear, and do with your Charm City weekend.
Sept. 30: Maritime Magic
Living Classrooms Foundation, 1417 Thames St. 7 p.m. $110.
For one night, the pier at the Frederick Douglass-Isaac Myers Maritime Park will transform into a foodie haven. Now in its 30th year, the big shebang will treat more than 2,000 guests to dozens of local restaurants from across the city, including old mainstays like Peter’s Inn, B&O American Brasserie, and the one-and-only Andy Nelson’s Barbecue; beloved go-tos like Hersh’s, Birroteca, and Parts & Labor; and new favorites like Cosima and Gunther & Co. Local beer will be on hand by Diamondback Brewing, Flying Dog, Key Brewing, and Union Craft, as well as local liquor by Sagamore Spirit, Lyon Distilling, The Baltimore Whiskey Company, and Blackwater Distilling. Under the stars (or tent, depending on the weather), hear the sounds of Cuban music and conga drumming by New Orleans’ Alexey Marti and Urban Minds followed by San Francisco’s funk and psychedelic-soul band, Con Brio. Best of all, in the heart of its waterfront campus, support one of Baltimore’s longest standing nonprofits, Living Classrooms, which has served disadvantaged youth and young adults in the city for more than 30 years.
Oct. 1: Meet Your Maker at WTMD
WTMD Studios, 1 Olympic Pl., Towson. 3-7 p.m. $30.
With all of the buzz surrounding Sagamore Spirit these days, it might seem like Kevin Plank is the only game in town. But his soon-to-be-local rye whiskey aside, Maryland is home to more than 45 local hooch creations. Bringing together the Land of Pleasant Living’s nine local distilleries, WTMD’s Meet Your Maker is the largest gathering of its kind to date in the state, and will include the likes of Stevensville’s Blackwater Distilling Company (Sloop Betty), St. Michaels’ Lyon Distilling Company (Lyon Rum), and Tenth Ward Distilling Company (White Caraway Rye), plus Charm City’s brand-new Old Line Spirits (Single Malt) and young-gun The Baltimore Whiskey Company (Shot Tower Gin). With your commemorative whiskey glass in hand, sample the goods and soak up the sounds of up-and-coming Baltimore bands, local folk group Hollywood Blanks and rockabilly trio High & Lonesome. Don’t worry about the forecast—the event is rain or shine.
Sept. 30-Oct. 2: Little Italy Madonnari Arts Festival
Little Italy, S. High St. Thu. 6-9:30 p.m., Fri. 4-10 p.m., Sat.-Sun. 11 a.m.-10 p.m. Free.
Rain won’t be the only thing painting the streets of Little Italy this weekend. Following the 16th-century tradition of Madonnari artists, the sidewalks and pavement will be turned into works of pastel and chalk art by dozens of local and international artists. In celebration of Italian Heritage Month, stop by their tents and admire as little strokes of color transform into awe-inspiring masterpieces. Throughout the weekend, indulge in as much homemade pasta and Italian wine as your heart could desire, and enjoy live music at the neighborhood’s various venues, like gypsy jazz at Germano’s Piattini on Friday night or steel pan drums at Amicci’s on Saturday. There will also be outdoor performances by the Annapolis Shakespeare Company and Baltimore Mandolin Quartet.
Oct. 1: Baltimore Jazz Festival
Druid Hill Park, 900 Druid Park Lake Dr. 12-8 p.m. Free.
The roots of jazz run deep in the city streets of Baltimore. In the early decades of the last century, this town brought us the likes of Billie Holiday, Cab Calloway, Chick Webb, Eubie Blake, Cyrus Chestnut, and Ethel Ennis, to name a few, and soon enough, Pennsylvania Avenue was home to hallowed stages graced by the likes of Louis Armstrong, Duke Ellington, Etta James, and Nat King Cole. A handful of decades later, the genre isn’t as prolific or vibrant as it once was, but in the pockets and corners of this city, you can still catch some of the best music in town, like on once-a-month Monday nights at An Die Musik with the Dunbar Alumni Jazz Band, or on Thursdays at Bertha’s with the Jeff Reed Trio. This weekend, celebrate the heritage of Baltimore jazz as well as its future with an all-day festival in beautiful Druid Hill Park. As part of Free Fall Baltimore, enjoy hot sax, Django-inspired guitar, and Wynton-esque trumpet, with Rumba Club, the Clarence Ward III All-Stars, Hot Club of Baltimore, Art Sherrod Jr., and the next generation of local musicians with the Dunbar Jazz Ensemble, all in tow. Rain or shine, bring the whole family to enjoy food from HarborQue and Ethel’s Creole Kitchen, Union Craft beer, and a petting zoo. .
Sept. 30-Oct. 2: Fells Point Fun Festival
Fells Point, S. Broadway & Thames St. Fri. 6-9 p.m., Sat. 11 a.m.-9 p.m., Sun. 11 a.m.-7 p.m. Free.
It’s going to be a bit soggy this weekend, but whatever the weather, the cobblestone streets of Fells Point will fill for three full days of food, drink, music, and celebrations of this historic neighborhood. Now in its 50th year, the lively little festival will honor its history—once upon a time, it was founded as an anti-highway fundraiser to save Fells from connecting to I-95 and I-83—as well as its ever-evolving days ahead. While old establishments continue to shutter (R.I.P. Leadbetter’s), promising new businesses continue to pop up (we see you, Treason Toting and Modern Cook Shop), and at the end of the day, the heart of the community remains the same, with swashbuckling blues lovers, eclectic historians, and tipped tourists still running amuck. Hear live music by 10 bands (including Waterfront Hotel and Cat’s Eye regular Sean K. Preston), indulge in street eats from local restaurants (like drool-worthy mini lobster rolls from Thames Street Oyster House), grab an orange cup, and raise a glass to the city’s 250-year-old waterfront.