At 12:45 p.m. on Saturday, October 24, a crowd of costumed children will leave Ross Elementary at 1730 R Street NW. They will head down 17th Street with trick-or-treat containers, stopping at Floriana, Annie's, Duke's, Commodore and Hank's/Back Door Taco on the way to a party at Stead Park. Three days later, on Tuesday night, the same blocks will be packed with thousands of spectators cheering drag queens, drag kings and community members as they race in heels.
Halloween falls on a Saturday this year. That puts Dupont Circle's Halloween across a full eight days instead of one night, with the busiest stretch of it on 17th Street. The Circle itself hosts the last event. Here is the week in order, with the details that matter if you live a few blocks away.
Saturday, October 24: Goblins on 17th, Rothko on 21st
The 15th annual Little Goblins Parade from Friends of Stead Park sets the tone for the week. Families gather at Ross Elementary starting at 12:30 p.m., the parade steps off at 12:45, and trick-or-treating runs past businesses on 17th Street down to Stead Park at 1625 P Street NW. The party there has games, music, crafts and snacks until 3 p.m. Families who skip the parade can come straight to the park any time after 1 p.m. The event happens rain or shine. Organizers suggest clothes and shoes children can play in, since there is a playground and plenty of hands-on activities, and they ask families to bring their own treat container.
The sponsor list covers the length of 17th Street. Treats come from Mikko, BarkSuds, DC Vegan, Agora, Swift Cleaners, Hank's/Back Door Taco, Floriana, Duke's, Doggy Style, Prego Again, Annie's, Commodore and Protest Pizza, and organizers say more are still to be confirmed. Program sponsors include the Ross Elementary PTA, the Garrison Elementary PTO, Foundry UMC, Keegan Theatre and DC's Department of Parks and Recreation. Registration is through the Friends of Stead Park event page.
The Dupont Circle BID's free Music in the Circle series has Sadia playing Dupont Circle Park that same Saturday from noon to 3 p.m., so the park and 17th Street are busy at the same hour.
Four blocks west, the Phillips Collection at 1600 21st Street NW opens Avery, Gottlieb & Rothko: By the Sea on October 24. It runs through January 24, 2027. The museum describes about 90 works tracing the friendship among Milton Avery, Adolph Gottlieb and Mark Rothko, and the exhibition's lead image is Avery's Black Sea from 1959. Members can see it early during free preview days on October 22 and 23. General admission is $20 for adults, $15 for seniors 62 and older, $12 for active and retired military, and $10 for students and educators with ID. Visitors 18 and under get in free. A family could walk the parade route at noon and reach the galleries by mid-afternoon without crossing Connecticut Avenue more than once.
Sunday, October 25: The Quiet Day Between
The year-round FRESHFARM Dupont Circle market runs from 8:30 a.m. to 1:30 p.m. on 20th Street NW between Massachusetts and Connecticut Avenues. FRESHFARM's Fall Forager program is running there now. From October 3 through November 29, shoppers collect digital stamps at participating markets and farm stands for a drawing for three $100 market gift cards.
From 10 a.m. to 3 p.m., Dupont Little Flea sets up at 1901 Q Street NW. This is its second October Sunday after October 18. The market and the flea are about two blocks apart, an easy errand loop on the one weekend day this week without a costume contest.
Tuesday, October 27: The Same Blocks After Dark
The 39th annual 17th Street High Heel Race comes back to the stretch where the Little Goblins Parade ran three days before. According to DC.gov, the race has been "Crossing The Line Since 1986." It began as a wager among drag queens, bartenders and community members to race in heels to each of the LGBTQIA+ bars along the strip. The founders of JR's Bar kept it going, and Mayor Muriel Bowser made it an Official Mayoral Event in 2018. The race is traditionally held the Tuesday before Halloween. A Saturday Halloween this year puts four days between the race and the holiday itself.
The basic schedule is below. Some details differ by source.
- Location: The official listing places the event on 17th Street NW between R and P Streets. DC.gov describes spectators lining the street from R Street to Church Street.
- Event window: The Eventbrite listing gives 6 to 10 p.m.
- Race start: Gay Travel 4U's September event guide lists racer registration at 7 p.m., a parade at 8 p.m. and the race at 9 p.m. The official pages do not confirm that run of show.
- Racers: Racers fill out the registration and authorization form at the tent on R Street.
- Community partners: The listing names JR's and Annie's Paramount Steakhouse, along with Dupont Circle Historic Mainstreet and ANC 2B.
Annie's is on both sponsor lists. It hands out candy to children on Saturday afternoon and partners on the race Tuesday night.
The 2026 street-closure and parking advisory had not been published as of mid-October. Last year's advisory from the Metropolitan Police Department, as PoPville reported it, listed parking restrictions from noon to 11 p.m. and vehicle closures from 2 to 11 p.m. on race day. That gives a rough idea of the impact, but it is not this year's notice. Residents who park on or near 17th Street should watch for the 2026 posting.
Friday and Saturday, October 30 and 31: The Circle Gets the Last Word
On Friday at noon, the Phillips holds a lunch-hour talk with Renée Maurer, "Duncan Phillips's Support of Avery, Gottlieb & Rothko," which runs until 1 p.m. It explains how the museum came to hold this work in the first place.
On Saturday, Halloween itself, the Dupont Circle BID holds its Fall Festival, Pumpkin Patch and Bluegrass Jamboree in Dupont Circle Park for the fifth year. Pumpkins are placed around the park while supplies last, and the BID provides art supplies for decorating them. There will be cornhole around the Circle, and Shannon Leigh and the Good Bygones will play bluegrass on the main stage. For the second year, there are three judged costume contests, one each for pets, kids and adults. First, second and third place in each win prizes, and top winners can receive up to $100 to spend at Dupont Circle restaurants.
The start time depends on the listing. The festival's Eventbrite page says 1 to 4 p.m. The BID's Music in the Circle schedule lists "Halloween & Bluegrass" in the same slot as its weekly noon-to-3 concerts. Arriving at 1 p.m. works under either schedule, and it gives pumpkins a little time to run out.
The Week at a Glance
| Date | Event | Where | Time |
|---|---|---|---|
| Sat, Oct 24 | Little Goblins Parade | Ross Elementary to Stead Park, via 17th St | 12:30–3 p.m. |
| Sat, Oct 24 | Music in the Circle: Sadia | Dupont Circle Park | Noon–3 p.m. |
| Sat, Oct 24 | By the Sea opens | Phillips Collection, 1600 21st St NW | Museum hours |
| Sun, Oct 25 | FRESHFARM market | 20th St NW, Mass. to Conn. Aves | 8:30 a.m.–1:30 p.m. |
| Sun, Oct 25 | Dupont Little Flea | 1901 Q St NW | 10 a.m.–3 p.m. |
| Tue, Oct 27 | 17th Street High Heel Race | 17th St NW, R to P Streets | 6–10 p.m. window |
| Fri, Oct 30 | Phillips curator talk | Phillips Collection | Noon–1 p.m. |
| Sat, Oct 31 | Fall Festival and Bluegrass Jamboree | Dupont Circle Park | Early afternoon |
After the Costumes Come Off
The weeks after Halloween fill up fast. On November 5, the Phillips holds a Phillips after 5 evening for the exhibition, called "Deep Sea Disco," from 5 to 8:30 p.m. A week later, on Thursday, November 12, the DC Holiday Market opens on the 1500 block of New Hampshire Avenue NW. It runs through December 23 and covers six weekends. This is the market's third year, and it is produced by Diverse Markets Management with the Dupont Circle BID. The BID says the vendor lineup will include art, jewelry, ceramics, vintage collectibles and handcrafts, with current hours at dcholidaymarket.net.
17th Street will also lose a long-running business. PoPville reported in September that the True Value Hardware at 1623–1627 17th Street NW, which has served the area since 1983, confirmed by email that it will close on December 31, 2026. The store gave no other details. That puts it on the same stretch where the goblins trick-or-treat and the racers run, and this will be its last fall season there. Anyone buying paint, hardware or household supplies on 17th Street this year still has until the end of December.
Many of these events depend on the businesses along 17th Street, so how the strip changes affects how Dupont spends its Halloween. If you are thinking about a home near 17th Street, or a sale timed around the neighborhood's busiest weeks, Infinity Group can explain how those blocks affect value and timing. Request a Private Market Consultation, and we will talk through Dupont Circle in detail.
