Join the Grilled Cheese Social at Sandlot Anacostia: The Rock Creek Social Club has a long history of raising the bar for social events in D.C., famously hosting the Good Life Tuesday parties at Recess, which showcased an eclectic mix of hip-hop, electro, go-go, and moombahton until its closure in 2012. In 2014, they introduced the Grilled Cheese Social day party on Marvin’s rooftop deck, where a combination of savvy DJs and a menu featuring delicious, gooey sandwiches created an unforgettable Saturday atmosphere. While Marvin is no longer around, the Grilled Cheese Social continues to thrive. This time, the fun shifts to Sandlot Anacostia, the first outdoor bar and music venue east of the river, developed by the same team behind Sandlots in Navy Yard, Tysons, and Georgetown. Expect an exciting mix of sounds from Rock Creek Social Club DJs, a special menu of grilled cheese sandwiches, and a vibrant crowd ready to enjoy a sunny day of festivities. 4 to 10 p.m. $20-$30.

    Experience Open Streets in Brookland: Following successful car-free days in Anacostia and Shaw, Brookland now gets its turn to embrace the Open Streets initiative. A half-mile stretch of 12th Street NE between Monroe and Franklin streets transforms into a lively playground on Saturday morning. Visitors can participate in rollerblading and e-scooter lessons, enjoy double Dutch and hula hooping zones, and partake in face painting, music, and family-friendly activities. Local restaurants and businesses will expand their outdoor seating areas onto the street, with favorites like Primrose and Brookland’s Finest participating in the festivities. 9 a.m. to 1 p.m. Free.

    Don’t Miss Amulet’s Performance at Pie Shop: The captivating duo Amulet, known for their dark and theatrical sound, has garnered a Washington Area Music Award nomination and is set to headline the popular H Street venue, Pie Shop, with their powerful rock ballads. The talented pair, comprising bassist MJ Phoenix and vocalist Stephanie Stryker, crafts cinematic, melodic, and bass-driven tunes that take listeners on a surreal journey. Attendees at their Pie Shop show can expect a night filled with “faerie dancers, tarot reading, and group rituals,” alongside three other musical acts that explore the darker side of music: Talking to Shadows, the Neuro Farm, and DJ Johnny Panic. 8 p.m. $15-$20.

    Immerse Yourself in the Maryland Renaissance Festival: Witches, wenches, knights, and jesters — the Renaissance Festival is back, ready to enchant visitors with live brawls, enormous smoked turkey legs, traditional ales, and hand-crafted treasures. Attendees are encouraged to dress in period costumes to fit this year’s theme: 1536. King Henry VIII is engaged in his third marriage while awaiting the execution of his second wife, Anne Boleyn. Thomas Cromwell will oversee the court’s proceedings as the regime begins to falter, and a nearby village prepares to welcome the king and his entourage. Events vary each weekend through late October, featuring professional performances, live music, and much more. Prepare for a weekend full of laughter and merriment! 10 a.m. $24 for adults through Sept. 11; $30 from Sept. 12 through Oct. 23.

    Explore the Dupont Circle Back-to-School Pop-up Market: As the new school year approaches, it’s not just kids who are in need of fresh looks and accessories. The Dupont Circle Main Streets’ seasonal pop-up market showcases over 50 vendors selling a variety of goods, including stunning jewelry, unique ceramics, captivating art, refreshing soap, and much more. The market extends along the sidewalks of Connecticut Avenue and P Street, with an information booth located at the north exit of the Dupont Circle Metro Station to provide maps and directions to attendees. This vibrant community event is a wonderful opportunity to discover new treasures while supporting local artisans. Noon to 5 p.m. Free.

    Join the Girls Pint Out Summer of Seltzers at DC Brau: Girls Pint Out is a national organization dedicated to women who appreciate craft beer and seek to connect with fellow beer enthusiasts in a welcoming environment. The local chapter in D.C. regularly hosts happy hours and brewery tours, and this month’s featured event centers on hard seltzer. Spend an afternoon at DC Brau, where you’ll take a guided tour of the seltzer-making process and sample their entire lineup of hard seltzer offerings, alongside “a few other surprises.” While the tour and tasting are exclusively for women, a meetup will be held afterward in the brewery open to everyone. This is a fantastic chance to learn and enjoy in a friendly atmosphere! 4 to 6:30 p.m. $15.

    Experience the Caribbean Crawl on U Street NW: U Street is known for its vibrant nightlife and diverse bar scene, and this exciting crawl takes participants on a journey to visit six of the most beloved locations over the course of just eight hours. Guests can dance to the rhythm of international DJs spinning the latest Afrobeats, reggae, Latin, and kompa music at themed stops in popular venues like Cloak & Dagger and Amsterdam Lounge. Kicking off at nightclub Elements, this event promises discounted drinks that vary by stop and exciting giveaways throughout the night. Gather your friends and prepare for a memorable evening filled with fun and cultural exploration! 2 to 10 p.m. $10-$20.

    Enjoy Live Music at Fairwood Music Festival at Fairwood Community Park: The Fairwood Music Festival marks the grand finale of Prince George’s County Parks’ annual concert series, returning to Bowie’s Fairwood Community Park after a two-year hiatus. This beloved festival features an impressive lineup of four performers, including smooth jazz artist Kevin Jackson, R&B sensation Elyscia, and the dynamic cover bands D.C. Fusion and the Exclusives. Attending this free festival is a fantastic way to enjoy an afternoon filled with live music and community spirit. Gather your friends and family, and don’t miss this exciting celebration of local talent! 1 to 6 p.m. Free.

    Participate in the Makers Market and Plant Swap in Silver Spring: Plants Alive!, a nursery and plant rental location in Silver Spring, is inviting guests to trade in their houseplants for a chance to acquire someone else’s prized greenery. During this engaging plant swap event, visitors can also explore a concurrent outdoor Makers Market featuring a variety of artistic creations from local vendors, including stunning jewelry, artisanal body care products, vintage clothing, and handcrafted candles, all available for purchase. This community event offers a refreshing way to connect with fellow plant enthusiasts and local artisans while discovering unique treasures. Noon to 4 p.m. Free.

    Laugh Along with Hilarious Colombian Americans at the D.C. Comedy Loft: The comedic ensemble Hilarious Colombian Americans, consisting of five talented stand-up comics — three from Colombia and two from the United States, all based in New York City — first collaborated during the 2019 New York Comedy Festival. Due to their overwhelming success, they are now on a national tour, featuring veteran Colombian actor Antonio Sanint, known for his roles in popular telenovelas like “Alicia en el País de las Mercancías,” who has also made a name for himself in stand-up comedy for over a decade. This talented group will grace the Comedy Loft stage, where they promise an entertaining night filled with laughter. The performance will be in English, with a sprinkle of Spanish for added flavor, ensuring that all attendees can enjoy the show. Please note, there is a two-item minimum (food or drink) per person. 7 p.m. $28.

    Explore ‘Art Pop: Visual Remembrance’ Workshop at the National Portrait Gallery: The After Five happy hours at the American Art Museum and National Portrait Gallery present a unique opportunity to unleash your creativity while enjoying a relaxed atmosphere. Illinois artist Donna Castellanos will lead a workshop in the Kogod Courtyard, where she’ll guide participants in creating their own portraits of loved ones using similar materials as her own selected portrait, “Bertha, I’d Like to Know Where You Got the Notion,” crafted from zippers, buttons, and fabric. All necessary supplies, along with two drink tickets, are included in the ticket price, making this an excellent chance to explore artistic expression while sipping on drinks. 5 to 7 p.m. $20.

    Kick Off the DC Jazz Festival at the Howard Theatre: While the headlining events of the annual DC Jazz Festival take place at the Wharf over the weekend of September 3 and 4, the musical festivities actually commence on Wednesday. The celebrated vocalist Kurt Elling, known for his extraordinary four-octave range, will showcase his talent at the Howard Theatre with his funky new ensemble, SuperBlue. Elling is renowned for his ability to twist and extend familiar melodies, seamlessly blending them with vocalese, all while maintaining an innate sense of swing. The evening will also feature D.C.’s own Christie Dashiell and her quartet as the opening act, promising an unforgettable night of jazz music. 8 p.m., $39.

    Join Tarot Night at Dew Drop Inn for a Mystical Evening: As the seasons shift from summer to autumn, it’s the perfect moment to re-center yourself, and what better way to do so than with tarot and cocktails? Join a “chill and witchy night” at the Dew Drop Inn, where attendees can enjoy tarot readings, participate in a tarot deck swap for those seeking a new set, enter a raffle, and sip on a special menu of “witchy” drinks. This enchanting evening promises to be a delightful blend of relaxation and mystical exploration. 7 p.m. Free.

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    Sienna Blake

    Sienna Blake is a licensed aesthetic consultant and beauty writer specializing in cosmetic surgery advancements and non-invasive treatments. With a background in dermatology and over eight years of industry experience, Sienna is passionate about helping people achieve confidence through informed beauty decisions. She holds a Bachelor's degree in Health Sciences and regularly collaborates with top plastic surgeons to stay at the forefront of aesthetic innovations. Outside of her work, Sienna enjoys traveling, skincare research, and practicing Pilates.

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