This weekend in the DMV is nothing short of a seasonal celebration–– from early Halloween celebrations and spooky-themed events to Wyclef Jean bringing Carnival vibes to the nation’s capital.
Washingtonians can test their knowledge of the city that raised them, while two Black woman-owned newspapers team up to celebrate contributions from local women leaders.
A guide to the weekend starts below. To keep up with all the fun, don’t forget to check out the Washington Informer Calendar.
Thursday, Oct. 22
The 51st’s Ask A D.C. Native, Live! Transit Edition
6:30 p.m. | Free
Metro Bar, 640 Rhode Island Avenue NE, Washington, D.C., 20002
“Step back, doors opening!” Join The 51st for “Ask A D.C. Native, Live!” — a trivia game show that tests D.C. natives’ knowledge about their hometown, in front of a live audience. This time, folks are diving into local transit at Metrobar, featuring chances to win prizes from local businesses and shop merch from local vendors.
Curated by Christina Sturdivant Sani, executive editor at The 51st, and hosted by poet and artist Dwayne Lawson-Brown, this event welcomes all — whether a D.C. native, longtime resident, or new to the nation’s capital.
Come early to settle in, purchase food and drinks, and show what Washington, D.C. means to you.
Friday, Oct. 23
Pinktober 2026: Dine, Sip & Support
11 a.m. – 3 p.m.| Select reservations
Hard Rock Cafe Washington DC, 999 E Street NW, Washington, D.C., 20463
Through Oct. 31, Hard Rock Cafe Washington DC is transforming into an all-out Pinktober affair, an annual breast cancer awareness campaign.
Enjoy limited-time Pinktober food and beverage specials, including: a Pink Power Bowl (at all company-owned locations) with farro, quinoa, lemon whipped feta, roasted red beets, and more;
Berry Lychee Spritz (free-spirited); and other healthy, refreshing ingredients.
A portion of proceeds from Pinktober food, beverage, and retail collection purchases will be donated to support breast cancer charities.
Enjoy the fun while giving back to an important cause.
7 p.m. – 11 p.m. | $75
National Zoo and Conservation Biology Institute, 3001 Connecticut Avenue NW, Washington, D.C., 20008
Night of the Living Zoo returns with an exciting evening of fun alongside furry friends.
Grab your friends and explore the Zoo after dark at this adults-only (21+) Halloween party with open bars, entertainers, live music, and after-hours animal viewing.
Saturday, Oct. 24
The Fall Calendar in Silver Spring: Halloween Events, Drinks & More
Noon | Varies by event and purchase
Commas Food Hall, 8661 Colesville Road, Level 3, Silver Spring, MD 20910
Commas Food Hall is bringing families, friend groups and date-night planners plenty of reasons to gather in downtown Silver Spring.
The food hall’s October calendar includes family-friendly fun and seasonal events for all ages, with this Saturday featuring Pumpkin Painting for All (Noon–5 p.m.), plus the Commas Costume Party from 4 to 8 p.m.
Oct. 25 highlights the Jack Skellington Character Brunch and Sunday Movie Night, featuring the “The Nightmare Before Christmas,” at 5 p.m.
Meanwhile, adults can enjoy Commas’ two new cocktail menus: Breast Cancer Awareness Month –– available through the end of October –– with drinks like the Tata-Tini (guava martini) and Life Elixir (color-changing gin and rose water drink), and its Fall Menu, featuring beverages like the Apple Pie, Falltini, Day of the Dead, and the Peach Cobbler through November.
AFRO Washington Informer High Tea
1 p.m. | $134.15+
National Press Club, 529 14th Street NW, Washington, D.C., 20045
The DC High Tea: Honoring women who educate, build, and lead!
Join The Washington Informer and AFRO News for an extraordinary afternoon celebrating phenomenal women whose leadership, vision, and dedication continue to inspire, empower, and shape communities.
Featuring distinguished honorees, inspiring hosts, and an afternoon of elegance, the event will honor a lineup of women making a lasting impact across education, media, public service, and leadership, such as: Dr. Dana A. Williams, dean of Howard University’s Graduate School; Dr. Kimberly R. Moffitt, dean of Howard University’s Cathy Hughes School of Communications; Jacqueline “Jackie” Jones, dean of Morgan State University’s School of Global Journalism & Communication; Dr. April Massey, chief academic officer at the University of the District of Columbia; Jacquie Gales Webb, Peabody Award-winning producer, performer and longtime host of “Sunday Afternoon Gospel” on WHUR-FM; and Dr. Myechia Minter-Jordan, CEO of AARP.
Sunday, Oct. 25
That’s So Vintage at The Square
10 a.m. – 2 p.m. | Free entry
The Square Food Hall, 1850 K Street NW, 5th Floor, Washington, D.C., 20006
This fall, Washington, D.C. gets another dose of the good stuff.
That’s So Vintage at The Square is D.C.’s biannual vintage shopping event, bringing together 40 of the East Coast’s most sought-after vintage collectors, dealers, and curators under one roof for a weekend dedicated to the rare, the unusual, and the genuinely vintage.
From rare designer finds and collectible Americana to vintage jewelry, records, cameras, art, prints, home goods, and one-of-a-kind accessories, That’s So Vintage is built for serious vintage lovers and anyone who knows that the best pieces are the ones that hold history.
Shoppers can expect to uncover everything from antique and vintage jewelry and delicate 1920s slip dresses to midcentury lighters, vintage cameras, 1950s workwear, 1970s graphic tees, eccentric 1980s needlepoint, rare Y2K designer pieces, vinyl records, art and prints, vintage home goods, and plenty of unexpected treasures in between.
Wyclef Jean Celebrates 30 Years of The Carnival
7 p.m. | $78.90+
Capital One Hall, 7750 Capital One Tower Road, Tysons, VA 22102
Capital One Hall presents Wyclef Jean in an electrifying one-night-only concert.
A defining force in popular music for more than two decades, Jean built an extraordinary career as both a solo artist and founding member of the legendary hip-hop group the Fugees. His distinctive sound draws from hip-hop, reggae, R&B, pop, Caribbean music, jazz, and classic rock.
Audiences will experience Jean’s music reimagined with the full power and scope of this thrilling performance — conducted by Jason Seber — and can look forward to favorites like “Gone Till November” and “We Trying to Stay Alive,” along with more from his celebrated career.
