Trail of Two Cities 5K, ‘Cabaret’ and a Packed Holiday Lineup Headline November in Ocean City

OCEAN CITY, NJ — Ocean City is gearing up for a bustling November as athletic traditions, live theatrical performances, and a full slate of holiday festivities take center stage across America’s Greatest Family Resort.

Causeway Run & Immersive Theatre Lead the Weekend

The action kicks off Saturday, Nov. 7, 2026, with the 31st annual running of the Trail of Two Cities 5K Run/Walk. One of the region’s premier autumn athletic traditions, the 3.1-mile point-to-point race gives participants panoramic bay views as they cross the Route 52 causeway in lanes typically reserved for vehicular traffic.

To keep logistics seamless, shuttle buses will operate from the finish line in Somers Point to transport participants to the Ocean City starting line prior to the race, as well as return runners to Ocean City once the event concludes. Online registration is currently open, with discounted pre-registration rates available through 4 p.m. on Thursday, Nov. 5. Runners and walkers can register and review race details at ocnj.us/race-events.

Later that evening, the spotlight shifts to the Ocean City Music Pier as the Ocean City Theatre Company (OCTC) debuts the Tony Award-winning Broadway musical “Cabaret.” Staged on Saturday, Nov. 7 at 7:30 p.m. and Sunday, Nov. 8 at 2 p.m., the production showcases high school performers in grades 9 through 12 from across the area.

Audiences can expect a completely reimagined venue: the Music Pier’s traditional general seating will be transformed into an intimate cabaret layout, immersing theatergoers in the evocative ambiance of Weimar-era Berlin’s Kit Kat Klub.

“Cabaret is an extraordinary piece of theater because it entertains, while also challenging us to think,” said OCTC Artistic Director Michael Hartman. “For our students, this production is an opportunity to develop as performers and as humans.”

Tickets are $15 and can be purchased online at oceancitytheatrecompany.com.

Holiday Festivities Just Around the Corner

Following this weekend’s events, the Ocean City Regional Chamber of Commerce and city partners will transition straight into the winter celebration season with a series of community favorites:

• Winterfest By The Sea (Saturday, Nov. 14): Hosted at the Ocean City Civic Center from 9 a.m. to 3 p.m., the sixth annual holiday shopping extravaganza features local craft artisans, food vendors, and unique seasonal gifts.

  Cape May Scanner

• Earlier than the Bird Downtown Shopping (Saturday, Nov. 21): Roll out of bed and head to Asbury Avenue in pajamas between 8 a.m. and noon to snag early-bird shopping discounts the weekend before Thanksgiving.

• Free Horse-Drawn Carriage Rides (Beginning Saturday, Nov. 21): Stroll or ride down Asbury Avenue with free carriage rides departing from Sixth Street and Asbury Avenue from noon to 3 p.m. on Nov. 21, Nov. 27–29, and continuing throughout December weekends.

• Fast & Furriest 5K Turkey Trot (Thursday, Nov. 26): Start Thanksgiving morning on the Boardwalk supporting the Ocean City Humane Society. Race registration and event info are available at hsocnj.org or by calling 609-398-9500 ext. 4.

• Christmas in the Downtown: “Our Miracle on Asbury Avenue” (Friday, Nov. 27): Skip the traditional Black Friday chaos for an old-fashioned downtown gathering from 2 p.m. to 5:30 p.m., capped off with Santa Claus arriving at 5 p.m.

• Ocean City Pops Holiday Show (Saturday, Nov. 28): Conductor Vince Lee leads the Ocean City Pops through beloved seasonal classics and modern hits at the Music Pier, with shows at 2 p.m. and 6 p.m. Tickets are available via oceancityvacation.com/boxoffice or by calling 609-399-6111.

• Santa Photos (Weekends Starting Nov. 28–29): Meet Santa downtown at Mark Soifer Park (9th & Asbury) from 9 a.m. to 11 a.m., or catch him stationed in a lifeguard boat outside the Music Pier from 1 p.m. to 3 p.m.

• Annual Ocean City Christmas Parade (Friday, Dec. 4): The holiday season hits full stride at 6 p.m. along Asbury Avenue. Parade participation and registration details are available at ocnj.us/christmas-parade.