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NYC This Week: May 2–3, 2026 — 40+ Events, 5 Boroughs

32,000 bikes, a cannabis parade, Cinco de Mayo, and the Pre-Met crowd all land in the same 48 hours. Good luck out there.

Insider intel for those who actually walk these streets.

🔥 THE BIG THREE — DON’T MISS

TD FIVE BORO BIKE TOUR 2026
Sunday, May 3, 2026 | All Day | All Five BoroughsThe city’s single most ambitious recurring event — 32,000 cyclists taking 40 miles of car-free roads across every borough in one shot. The route runs from Lower Manhattan through the Bronx, Queens, Brooklyn, and finishes on the FDR Boardwalk in Staten Island. If you’re not riding it, spectating along the course is its own event. The BQE stretch is the one — nothing looks more like New York than that road full of bikes with the skyline behind it. Staging begins at Bowling Green at dawn.

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54TH ANNUAL NYC CANNABIS PARADE & RALLY 🆓
Saturday, May 2, 2026 | 12:00 PM – 6:00 PM | Greenwich Village + Union Square, ManhattanThe parade steps off from Washington Square Park arch at noon and the rally locks down Union Square South through 6 PM. The 54th year of this thing — New York’s longest-running counterculture parade, and it still draws a crowd that knows how to make a Saturday look like a Saturday. Washington Square in May at peak march energy is one of the great street photography environments in the city. The Million Mushroom March contingent files out of the arch at 12:30 sharp.

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CINCO DE MAYO NYC PARADE 2026 🆓
Sunday, May 3, 2026 | 1:00 PM – 3:30 PM | West 106th Street between Central Park West and Manhattan Avenue, ManhattanThe city’s official Cinco de Mayo parade rolls through the Upper West Side on Sunday afternoon. West 106th between CPW and Manhattan Avenue is one of the most photogenic parade corridors in Manhattan — the park wall on one side, the brownstones on the other. Stack this with the 5 De Mayo Fiesta block festival on East 116th Street (noon–6 PM) for a full day. [Internal Link: NYC Cinco de Mayo Guide — Where to Be, Borough by Borough]

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📡 SET WATCH & PARTY CRASHER

Are you a party crasher or a shooter looking for a backdrop? Check these out.

Devil Wears Prada 2 — Union Square Plaza, Manhattan (Sunday all day)
The production has Union Square Plaza locked between 17th and 18th Street on Broadway. This is a full studio film shoot in one of the city’s busiest pedestrian plazas. Work the perimeter — talent trailers, period-dressed extras, and the kind of organized chaos that makes for completely accidental editorial photography.

FAENA Hotel Pre-Met Dinner — West 18th Street at 10th Avenue, Chelsea (Sat May 2, 5 PM–10 PM)
The Met Gala is Monday. The pre-gala circuit starts tonight in Chelsea. FAENA has West 18th between 10th and 11th locked for their dinner. Fashion week energy, designer cars, and people who dress like the occasion. The Meatpacking/Chelsea border at dusk is the backdrop.

Wall Street Journal Future of Everything — West 49th Street at 11th Avenue, Hell’s Kitchen (Sat–Sun)
WSJ’s major conference has a full production footprint on West 49th. Tech, media, and finance crowd in business casual moving between the Javits corridor and the Hudson Yards stretch. Street scene worth documenting if you’re working uptown.

🗺 BOROUGH-BY-BOROUGH BREAKDOWN

SATURDAY, MAY 2, 2026 — MANHATTAN
The Great Saunter 🆓 — Upper West Side to All of Manhattan
7:00 AM – 7:00 PM | Starts at Riverside Park, 72nd–95th Street
The Shorewalkers’ annual 32-mile circumnavigation of Manhattan island on foot. The whole perimeter, in one day. It’s free, it’s epic, and the people who do it every year are a particular kind of New Yorker you need to meet. Join for a segment or commit to the whole thing — either way you’ll end up somewhere you’ve never been.
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Buddha Blessing Ceremony in Times Square 🆓 — Midtown, Manhattan
10:00 AM – 4:30 PM | Times Square 46th/47th Broadway Pedestrian Plaza
A full Buddhist blessing ceremony planted in the middle of Times Square for a Saturday. The visual contrast — robes and incense against the LED towers — is one of the more genuinely surreal things this city does every year. All day, all free.
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2nd Avenue Community Benefit Festival 🆓 — Upper East Side, Manhattan
10:00 AM – 6:00 PM | 2nd Avenue between East 66th and East 86th Street
Twenty blocks of the UEA’s Second Avenue handed to vendors, food, and community programming. This is one of the longer street fair stretches in the borough and it runs right through the museum mile corridor. Stack it with a Met visit or the Lexington corridor.
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Columbia University 14th Annual Powwow 🆓 — Morningside Heights, Manhattan
9:00 AM – 5:00 PM | Heckscher Playground Lawns, Central Park
Columbia’s Native American Council brings Indigenous dancers, drums, regalia, and community to the Central Park lawns for a full day. One of the most visually and culturally significant free events in the city every spring, and most of the city walks right past it. [Internal Link: Indigenous NYC — A Guide to Cultural Events in the Five Boroughs]
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PEN World Voices Festival: Indie Lit Fair 🆓 — Greenwich Village, Manhattan
12:00 PM – 5:00 PM | Washington Square South between Sullivan and Thompson
Independent publishers, writers, zines, and books that don’t exist in any chain store. Washington Square South turns into a proper literary market. If you’re already at the Cannabis Parade in the park, step half a block south and stay for this.
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Art Celebration Block Party 🆓 — West Village, Manhattan
11:00 AM – 7:30 PM | Leroy Street between Greenwich Street and Hudson Street
A full block party on one of the West Village’s best-looking blocks. Leroy Street at Hudson is cobblestone, landmarked, and genuinely the kind of street that makes people move to this city. An art-focused block party here hits differently.
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4th Annual West Harlem Summer Jazz Fest 🆓 — Harlem, Manhattan
12:00 PM – 4:00 PM | Jackie Robinson Park Bandshell, Harlem
Four hours of live jazz in the Jackie Robinson Park bandshell. This is the real Harlem cultural calendar — not a ticketed event, not a sponsored activation, just a community jazz festival on a Saturday afternoon in a park named after Jackie Robinson. Be there.
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Summer on the Hudson: Star Gazing 🆓 — Upper West Side, Manhattan
7:30 PM – 11:00 PM | 70th Street Pier Plaza, Riverside Park South
End Saturday on the Hudson with a free stargazing session at the 70th Street Pier. Dark enough to see something, warm enough to stay, and the river moving quietly next to you. That’s a New York night.
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SATURDAY, MAY 2, 2026 — BROOKLYN
Dorothy Day Street Renaming Ceremony 🆓 — Brooklyn Heights, Brooklyn
11:00 AM – 12:00 PM | Pineapple Street between Henry Street and Hicks Street
Brooklyn Heights is officially co-naming a block for Dorothy Day — Catholic activist, journalist, and one of the most genuinely radical figures the city ever produced. Pineapple Street in Brooklyn Heights on a Saturday morning is already worth the visit. Add a street renaming ceremony and you have something real.
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AFSP NYC Paws for Prevention 🆓 — Coney Island, Brooklyn
9:00 AM – 12:00 PM | Steeplechase Pavilion, Coney Island Beach & Boardwalk
The American Foundation for Suicide Prevention’s dog walk on the Coney Island boardwalk. Steeplechase Pavilion in early May, dogs everywhere, the Atlantic as the backdrop. The boardwalk before the summer crowds arrive is a different place entirely.
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The Less Popular Brooklyn Half Marathon 🆓 — Bay Ridge, Brooklyn
8:00 AM – 12:00 PM | Shore Parkway Bike Path, Bay Ridge
Named honestly. The Shore Parkway path along the Narrows in early May with the Verrazzano looming ahead is one of the most underrated running and spectating spots in the city. Come for the race, stay for the bridge views.
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SATURDAY, MAY 2, 2026 — QUEENS
NYRR Mindful 5K 🆓 — Flushing, Queens
8:00 AM – 11:00 AM | Flushing Meadows Corona Park
A 5K run around the Unisphere loop. FMCP in early May morning light is legitimately one of the most photogenic running environments in the five boroughs — the globe, the reflecting pool, the old World’s Fair pavilions. Free to spectate.
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SATURDAY, MAY 2, 2026 — BRONX
Run the Bronx 🆓 — University Heights, Bronx
10:00 AM – 1:00 PM | Hall of Fame Terrace between Sedgwick Avenue and University Avenue
A race that starts and finishes at the Hall of Fame for Great Americans on the old NYU Bronx campus — now Bronx Community College. The Hall of Fame terrace overlooking the Harlem River Valley is one of the most unknown great views in the city. The race is the reason to finally go see it.
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VCP 50K Ultra — Van Cortlandt Park 🆓 — Woodlawn, Bronx
7:00 AM – 3:00 PM | Van Cortlandt Park Cross Country Course
Fifty kilometers of Van Cortlandt Park’s trail system. If you’ve never watched ultramarathon runners work through the cross-country course here, it’s something — the old-growth forest, the dirt paths, the occasional deer. Free to spectate anywhere on the trails.
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SUNDAY, MAY 3, 2026 — MANHATTAN
47th Annual Plantathon Festival 🆓 — Upper West Side, Manhattan
10:00 AM – 6:00 PM | Broadway between West 73rd and West 82nd Street
Nine blocks of Broadway transformed into a plant market, vendor fair, and community gathering. The 47th year. This is the Upper West Side at its most neighborhood — the greenery, the brownstones, the stroller brigades. Stack it with the Cinco de Mayo Parade a few blocks north at 1 PM.
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Bryant Park Community Fair 🆓 — Midtown, Manhattan
10:00 AM – 6:00 PM | West 41st Street between 6th and 7th Avenue
Bryant Park’s community fair spills onto West 41st with vendors and activities on one of Midtown’s best pedestrian blocks. The park lawn in early May is fully open, the library’s back terrace is accessible, and the crowds are manageable before summer hits.
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Arise New York 🆓 — Upper West Side, Manhattan
12:00 PM – 6:00 PM | Central Park Bandshell
A full afternoon at the Central Park Bandshell — community performances, music, and the kind of programming that makes the bandshell the democratic heart of the park. Six hours of free programming. Get there early and stay late.
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Andy Kessler Skate Jam 🆓 — Upper West Side, Manhattan
12:00 PM – 4:30 PM | Riverside Park Skate Park Plaza
The annual memorial skate jam at the Riverside Park skate plaza — one of the better concrete spots in Manhattan. Sunday afternoon skating on the Hudson side of the park, open to all levels, free to watch. The skate park sits just above the river with a view that nobody advertises.
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Jazz at Ellison Island 🆓 — Upper West Side, Manhattan
1:00 PM – 6:00 PM | Ellison Island, Riverside Park
Live jazz on Ellison Island — a little wooded peninsula in Riverside Park that most people walk past without knowing it exists. Five hours of music, the Hudson moving behind the bandstand, Sunday afternoon light through the trees. This is what the city is actually for.
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5 De Mayo Fiesta Block Festival 🆓 — East Harlem, Manhattan
12:00 PM – 6:00 PM | East 116th Street between Third and Second Avenue
El Barrio’s Cinco de Mayo block festival — the neighborhood version, not the sponsored one. East 116th between 2nd and 3rd is the cultural spine of East Harlem and it’s at full power on a Cinco de Mayo Sunday. Stack this with the El Barrio Family Day Health Fair happening nearby.
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Lucille Lortel Awards 🆓 — Greenwich Village, Manhattan
5:30 PM – 7:00 PM | LaGuardia Place between Washington Square South and West 3rd Street
Off-Broadway’s biggest night. The Lortels honor the best of the off-Broadway season and the ceremony spills onto LaGuardia Place. Theater people in their best on a Sunday evening in the Village — the red carpet energy is real even if the venue is small.
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SUNDAY, MAY 3, 2026 — BROOKLYN
Greenpoint Avenue Fair 🆓 — Greenpoint, Brooklyn
10:00 AM – 6:00 PM | Greenpoint Avenue between 42nd and 48th Street
Six blocks of Greenpoint Avenue in full street fair mode on a Sunday. Greenpoint in May is already one of the better neighborhoods to just walk — add vendors, food, and the Polish-immigrant-meets-hipster energy and you’ve got a full afternoon. The pierogi stands alone are worth the G train.
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Polish Flag Day Parade 🆓 — Greenpoint, Brooklyn
11:00 AM – 4:30 PM | McGuinness Boulevard between Nassau Avenue and Norman Avenue
Greenpoint’s Polish community marches on McGuinness on Polish Flag Day. This neighborhood still has one of the largest Polish communities in the Western hemisphere, and when they parade it is the real thing — flags, traditional dress, the works. Stack this with the Greenpoint Avenue Fair nearby.
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Cinco de Mayo & Mother’s Day Parade 🆓 — Bay Ridge, Brooklyn
2:00 PM – 5:00 PM | 59th Street between 4th and 5th Avenue
Bay Ridge combines Cinco de Mayo and Mother’s Day into one parade — which is exactly the kind of move this neighborhood makes. The 59th Street commercial strip in Bay Ridge is one of the most authentic outer-borough parade corridors in the city. [Internal Link: Bay Ridge Brooklyn — The Neighborhood Guide]
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Church Avenue Street Fair 🆓 — Flatbush, Brooklyn
10:00 AM – 6:00 PM | Church Avenue between East 10th Street and Argyle Road
Church Avenue in Flatbush is one of the most genuinely diverse commercial strips in New York — Caribbean bakeries, Bangladeshi grocers, Haitian restaurants, West African textiles. A street fair here is a full passport stamp. Go hungry.
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Bang on a Can: Crossing Open Ground 🆓 — Fort Greene, Brooklyn
12:00 PM – 1:00 PM | Monument Plaza, Fort Greene Park
Bang on a Can brings contemporary classical music to the Fort Greene Park monument. One hour, free, outdoors, one of the most interesting contemporary music organizations in the city. The monument plaza at noon on a Sunday is already a good place to be.
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SUNDAY, MAY 3, 2026 — QUEENS
Festival del Trabajador Migrante 🆓 — Corona, Queens
2:00 PM – 7:00 PM | Corona Plaza, Roosevelt Avenue between National Street and 104th Street
The Migrant Worker Festival fills Corona Plaza on a Sunday afternoon — music, food, community organizing, and the full energy of one of the most densely populated immigrant neighborhoods in the Western Hemisphere. Corona Plaza is one of the great public spaces in the outer boroughs and this is its kind of event.
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3rd New York Ouyue Cultural Festival 🆓 — Flushing, Queens
10:00 AM – 6:00 PM | Sanford Avenue between Main Street and Kissena Boulevard
A Chinese regional cultural festival — Ouyue culture representing the Zhejiang and Jiangxi traditions — on Sanford Avenue in Flushing. Traditional performance, food, and the full depth of what Flushing actually is beyond the soup dumplings. This is the event that makes Flushing the most interesting neighborhood in the outer boroughs.
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Procession in Honor of Our Lady of She-Shan 🆓 — Flushing, Queens
1:00 PM – 4:00 PM | 139-25 35th Avenue, Flushing
A Catholic procession honoring the Chinese Marian tradition of Our Lady of Sheshan — a pilgrimage site near Shanghai that has enormous significance for Chinese Catholics globally. The Flushing Chinese Catholic community processes through the neighborhood in full devotional regalia. Quiet, profound, and almost entirely unnoticed by the rest of the city.
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SUNDAY, MAY 3, 2026 — BRONX
Rites of Drum 🆓 — South Harlem / Central Harlem boundary, Manhattan
12:00 PM – 6:00 PM | Marcus Garvey Park Amphitheater, Harlem
Six hours of drum-centered performance and community gathering at the Marcus Garvey Park amphitheater. The amphitheater at Mt. Morris Park is one of the great underused outdoor performance venues in the city — stone seating, acoustics, history. Rites of Drum fills it right.
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Salsa in the Street 🆓 — Riverdale, Bronx
3:00 PM – 6:00 PM | West 239th Street between Broadway and Review Place
A single block festival in Riverdale — the Bronx’s northernmost and most architecturally surprising neighborhood — dedicated to salsa. Three hours of live music on a block that most of the city has never been to. This is exactly the kind of event that makes the outer borough calendar worth reading.
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SUNDAY, MAY 3, 2026 — STATEN ISLAND
Spooky Staten Island History & Nature Night Hike 🆓 — Tottenville, Staten Island
7:00 PM – 8:00 PM | Conference House Park Visitor Center, Satterlee Street and Hylan Boulevard
National Paranormal Day lands on Sunday and the Rangers are celebrating properly — a night hike through Conference House Park exploring the weird, the strange, and the genuinely spooky history of Staten Island’s southernmost tip. The Conference House itself is one of the most historically significant buildings in the five boroughs and almost nobody has been inside. This is the reason to go.
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🏃 FREE FITNESS / OPEN RUNS 🆓

NYRR Open Run — Every Saturday 8:45 AM: Astoria Park (Astoria, Queens), Baisley Pond Park (South Jamaica, Queens), Canarsie Park (Canarsie, Brooklyn), Crocheron Park (Bayside, Queens), Highland Park (Woodhaven, Queens), Inwood Hill Park (Inwood, Manhattan), Shore Road Park (Bay Ridge, Brooklyn), Soundview Park (Soundview, Bronx), St. Mary’s Park (Mott Haven, Bronx).

NYRR Open Run — Every Sunday 8:45 AM: Conference House Park (Tottenville, Staten Island), Cunningham Park (Fresh Meadows, Queens), Marine Park (Marine Park, Brooklyn).

Summer on the Hudson: Tai Chi 🆓 — Sunday, May 3, 8:00 AM – 9:30 AM | Soldiers’ and Sailors’ Monument, West 89th Street and Riverside Drive, Manhattan. Start Sunday right.

Summer on the Hudson: Over, Under, Through 🆓 — Sunday, May 3, 11:00 AM – 12:00 PM | Parkour Park, Riverside Park South, Manhattan. All ages, all levels.

Summer on the Hudson: Parkour Kickoff 🆓 — Sunday, May 3, 11:00 AM – 2:00 PM | Riverside Park South, 67th Street Wooden Overlook, Manhattan.

Crotona Park 5K 🆓 — Saturday, May 2, 9:30 AM | Crotona Park Amphitheater, Crotona, Bronx.

Run the Stuy 5K 🆓 — Sunday, May 3, 7:30 AM | Lewis Avenue between Decatur and Macdonough, Bed-Stuy, Brooklyn.

📋 ALSO THIS WEEK

  • Sat–Sun, 8 AM – Old Cathedral Outdoor Market, Prince Street, SoHo, Manhattan 🆓 (through 8 PM both days)
  • Sat–Sun, 8 AM – Pompeii Flea Market, Bleecker Street, West Village, Manhattan (through 8 PM both days)
  • Sat, 6 AM – Inwood Greenmarket, Inwood, Manhattan (to 5 PM)
  • Sat, 6 AM – Down to Earth Chelsea Farmers Market, Chelsea, Manhattan (to 6 PM)
  • Sat, 8 AM – 82nd Street Greenmarket, Upper East Side, Manhattan (to 5 PM)
  • Sun, 6 AM – Down to Earth Park Slope Farmers Market, Park Slope, Brooklyn (to 6 PM)
  • Sun, 8 AM – Carroll Gardens Greenmarket, Carroll Gardens, Brooklyn (to 5 PM)
  • Sun, 8 AM – Cortelyou Greenmarket, Flatbush, Brooklyn (to 5 PM)
  • Sun, 8 AM – Forest Hills Greenmarket, Forest Hills, Queens (to 5 PM)
  • Sun, 8 AM – Jackson Heights Greenmarket, Jackson Heights, Queens (to 5 PM)
  • Sun, 8 AM – Columbia Greenmarket, Morningside Heights, Manhattan (to 6 PM)
  • Sun, 5:30 AM – Murray Hill Farmers Market, Murray Hill, Manhattan (to 7:30 PM)
  • Sat–Sun, 11 AM – Fordham Road BID Sidewalk Sale, Fordham, Bronx 🆓 (to 7 PM)
  • Sat–Sun, 9 AM – St. Anthony Flea Market, Greenwich Village, Manhattan 🆓 (to 7 PM)
  • Sat, 9 AM – Methodist Flea Market, Jackson Heights, Queens (to 5 PM)
  • Sat, 2 AM – Macy’s Flower Show continues, Herald Square, Manhattan 🆓 (All Day)
  • Sat, All Day – Special Waste Drop-Off events all 5 boroughs 🆓
  • Sat, 9 AM – Pinkster Festival, Van Cortlandt House Museum, Woodlawn, Bronx 🆓 (to 4 PM)
  • Sat, 10 AM – Riverkeeper Sweep, Randall’s Island + WNYC Transmitter Park + Valentino Pier 🆓
  • Sat/Sun – Multiple It’s My Park volunteer cleanup events citywide 🆓
  • Sat, 9 AM – Birding: Warbler Watch, Forest Park Overlook, Woodhaven, Queens 🆓 (to 10 AM)
  • Sat, 10:30 AM – Shoreline Cleanup, Inwood Hill Park, Inwood, Manhattan 🆓 (to noon)
  • Sat, noon – Pinkster Festival, Van Cortlandt Park, Bronx (to 4 PM) — Caribeando Music & Dance Workshop at 2 PM same location

📅 NARRATIVE LOOK AHEAD

Here it is — the weekend that finally flips the calendar to summer mode. The Five Boro Bike Tour on Sunday is the city’s unofficial opening day, 32,000 cyclists parting the BQE like a slow-moving river of spandex and steel while the rest of the boroughs figure out what to do with car-free streets for six hours. Saturday builds the tension: the Cannabis Parade takes Washington Square at noon, the Columbia Powwow brings Indigenous ceremony to Central Park, the Great Saunter circles the entire island on foot, and somewhere in Chelsea the pre-Met dinner crowd is already figuring out what to wear. Sunday delivers five parades across three boroughs, Jazz on the Hudson, bang on a can in Fort Greene, salsa in Riverdale, and a night hike through Staten Island’s haunted southernmost tip. The Met Gala is Monday — the city is already dressed for it. See you in the streets.

Know an event we missed? If you have events you want to add to our list, email us at howard@nycinfocus.com

Details as filed — verify with organizers before you go. | nycinfocus.com


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