The best things to do in Washington, D.C. this week: August 31-September 4

DC JazzFest at The Wharf is the rare festival that actually feels like it belongs to the city. The waterfront transforms into a living, breathing jazz hub, with music spilling out from every corner and a crowd that’s as diverse as the lineup. The DCJazzPrix competition is always a highlight, drawing serious talent from around the globe, but the real magic happens in the smaller moments: a late afternoon set with the river as backdrop, or a candid “Meet the Artist” chat that leaves you thinking about music in a new way. Arena Stage hosts some of the festival’s most anticipated performances, but don’t sleep on the pop-up gigs and spontaneous collaborations that seem to materialize out of nowhere. If you want to see how jazz fits into the city’s present, not just its past, this is the weekend to do it.

James Taylor’s voice has a way of making even the most cavernous venues feel intimate, and that’s not something you get from just any legacy act. There’s a quiet confidence in the way he delivers the songs you’ve known for decades, but it’s the subtle shifts and lived-in warmth that keep his performances from ever feeling like a nostalgia trip. If you’ve caught him live before, you know he’s not interested in coasting on old hits—he’s always got a few surprises tucked into the setlist, and his rapport with the crowd is as genuine as it gets. This is the kind of night that sneaks up on you: you come for the classics, but you leave remembering the moments in between. If you’re overdue for a reminder of how good a familiar song can feel, this is your chance.

ALOK’s “Eat Pray Leave” tour should appeal to anyone who likes their comedy with a little more on its mind. Their work moves between stand-up, poetry and personal storytelling, often taking on gender, identity and the strange social rules that shape everyday life. That mix makes this a more interesting pick than a standard night of jokes, especially at the Lincoln, where the intimate room suits a performer whose material depends on direct connection with an audience. ALOK has also built a body of literary work around these same questions, so the comedy comes with a point of view that extends beyond the stage. If you know their work from Netflix’s “Gender Agenda” or their writing, this is a chance to see that perspective developed in a live setting.

The Hirshhorn’s Basquiat x Banksy exhibition gets a soundtrack of its own with this gallery experience, pairing the visual work with a live musical response that traces connections between hip-hop, trip-hop and the art on the walls. Rather than treating the exhibition as something to quietly walk through, the program asks how rhythm, sampling and beat-making can change the way you read an image. The result should be especially appealing if you have already seen the show and want a reason to return with fresh ears. The musical program moves across styles associated with the artists’ cultural landscape, giving the experience a distinctly sound-driven focus without turning the galleries into a conventional concert space. For anyone interested in the overlap between street art and music, this is a chance to consider Basquiat and Banksy through a different medium, with the museum itself becoming part of the experiment.

Academy Tortillas & Tequilas is getting the Bucket Listers treatment with a Taste of DC event that puts its Mexican menu through a more focused lens. The draw here is the chance to sample the restaurant’s tortillas and tequila offerings in one sitting, rather than committing to a full dinner and hoping you picked the right things. It’s a useful format for anyone who has been meaning to check out the spot, especially with a group that prefers grazing to a formal meal. The experience also makes sense as a neighborhood food stop before heading elsewhere for the night. If you already know Academy, this is a chance to revisit it with a little more structure; if you don’t, the tasting setup offers an easy introduction without overthinking the order.

Gabriel Rutledge has the kind of comedy career built on road miles rather than hype, and that comes through in his material. His book, “Happiness Isn't Funny,” turns life as a touring comic into a source of stories, while his specials lean into the dry, observational side of stand-up. The Comedy Loft is a good setting for that approach, particularly if you prefer comics who can make everyday frustrations funny without turning every bit into a big performance. Rutledge has also won both the Seattle International Comedy Competition and Atlanta's Laughing Skull Comedy Festival, so there is plenty of club pedigree behind the low-key delivery.

I Regret Nothing is the sort of one-person show that earns its laughs by refusing to tidy up the embarrassing parts. Sara Polon tells the story of a successful entrepreneur who finds herself badly out of her depth, tracing a path that includes bombing on a New York comedy stage and an unfortunate 4am trip to the ER. The premise sounds like a setup for a collection of punchlines, but the show is billed as a story about the things people rarely talk about, with the messiness and vulnerability left intact. That gives the comedy some weight without turning the evening into a therapy session. Running September 1 through 3 at the National Union Building, the 90-minute show starts at 7:30pm, with doors opening an hour earlier for drinks. If you like personal storytelling that can get uncomfortable before finding its way back to a laugh, this is a worthwhile small-room outing.

Wordplay Wednesday is a smart way to make a museum visit feel less like homework and more like a night out. The Back-to-School Edition keeps all three floors of Planet Word open after hours, with word-based games and puzzles alongside the interactive Unlock the Music karaoke gallery and the Joking Around humor gallery. The back-to-school theme gives the evening a playful excuse to revisit the kind of language games that usually disappear once the school year starts, while complimentary treats and a pop-up bar from Immigrant Food keep it firmly in after-work territory. Educators get their own lounge with activities, treats and raffle prizes, but you do not need to work in a classroom to get something out of the night. Admission is pay what you can, from $5 to $25, making this one of the more accessible ways to spend a Wednesday evening downtown.

Sunset Cinema is a summer ritual worth keeping on the calendar, especially when the movie selection gives you a reason to show up early and stay awhile. The free Wednesday series takes over Transit Pier with a lineup that moves comfortably between crowd-pleasers and cult favorites, from Shrek 2 and Hairspray to Roman Holiday and 10 Things I Hate About You. The waterfront setting does plenty of the work: bring a blanket or folding chair, grab food from a Wharf restaurant and settle in as the evening cools down. The final screening on September 2 is a double feature, pairing When Harry Met Sally with The First Wives Club, with the first film starting at 7pm and a short intermission between movies. It is a low-effort way to make a weeknight feel like an occasion, without spending anything on admission.

Junkyard Band’s 50th anniversary celebration is a good excuse to spend a Thursday night with one of go-go’s most unmistakably DC institutions. The group’s story starts in Barry Farm in 1980, when kids built rhythms from plastic buckets and soda cans before taking those street-born sounds to talent shows, local stages and eventually national audiences. That history matters here because Junkyard has always carried the music’s neighborhood roots with it, rather than treating go-go as nostalgia. At the Hamilton, the setup should make that history feel especially close: the front tables are being cleared for a general admission pit, giving the night some much-needed room to move. For anyone who came of age with DC go-go, this is a chance to hear a foundational local band in a celebratory setting. For newer listeners, it is a direct connection to the culture that shaped the city’s sound.