White Plains Events Calendar: Festivals, Concerts & Things to Do (2026 Guide)

Wondering what’s happening in White Plains? Fall is the city’s busiest season — Oktoberfest shuts down Mamaroneck Avenue, Broadway tours play the Performing Arts Center, and the holiday lights cap it all off. Here’s your White Plains events calendar for October through December 2026, all verified against official sources. Dates marked “TBA” are beloved annual traditions whose 2026 dates hadn’t been announced at press time.

October 2026 — Fall Festival Season

Downtown White Plains Oktoberfest — Sunday, Oct 11, 1–6pm

The big one. Mamaroneck Avenue (between Maple Ave and Quarropas St) closes to traffic for an afternoon of German food, beer wristbands, a live oompah band, and contests — stein-holding, alpine horn, and frankfurter toss. Rain or shine, and it draws thousands. Get there early for the best food lines.

Dear Evan Hansen — Oct 2–25, White Plains Performing Arts Center

The Tony-winning Broadway musical plays 11 City Place for nearly the whole month. One of the biggest theater bookings downtown has seen this year — weekend shows will sell out.

White Plains Halloween Parade — Sunday, Oct 18, 7pm

The city’s annual Halloween parade runs from Library Plaza to Court Street. A genuine local tradition and great for families — costumes encouraged, obviously.

REV FEST 250: Battle of White Plains Reenactment — Oct 24–25, Ward Pound Ridge Reservation (nearby)

Part of the America 250 celebrations: 500 living historians, Continental and British encampments, and a large-scale battle reenactment of the 1776 Battle of White Plains. A short drive from downtown and worth it for history buffs.

Freestyle Forever Concert — Saturday, Oct 24, 8pm, Westchester County Center

An 80s/90s freestyle lineup — TKA, George Lamond, Judy Torres, Shannon, Cynthia, The Cover Girls and more — at 198 Central Ave. Nostalgia sells, so don’t wait on tickets.

Halloween Bar Crawls — Saturdays, Oct 24 & Oct 31

Two organized crawls: Oct 24 starting at Cantina Taco & Tequila Bar (4pm), and Oct 31 starting at Ron Blacks Beer Hall on Mamaroneck Ave (3pm). Costumes required in spirit, if not in the rules.

More October dates

Oktoberfest Pre-Party — Fri Oct 2, 4–8pm, downtown bars and restaurants. Drink specials and giveaways ahead of the main event.

Outdoor Movie: Hamilton — Fri Oct 2, Battle of White Plains Park.

Halloween Pumpkin Patch — Sun Oct 4, 2pm, Gillie Park.

Tony Dabas (comedy) — Fri Oct 30, 7–10pm, Westchester County Center. $60 includes dinner, free parking.

Fall Westchester County Home Show — Sat Oct 31 & Sun Nov 1, Westchester County Center.

Howl-o-Ween Bash — Sat Oct 24, 3pm, Bark Dog Park. Costumes for dogs.

Saturday Night Laughs (comedy) — Sat Oct 24, 8pm, Tre Angelina, 478 Mamaroneck Ave.

November 2026 — Concerts, Basketball & Lights

Megan Hilty in Concert — Saturday, Nov 14, White Plains Performing Arts Center

The Broadway star (Wicked, Smash) brings a concert evening to 11 City Place.

Westchester Knicks Home Games — Nov 14, 25, 27 & 29, Westchester County Center

The Knicks’ G League squad plays downtown all month, with games continuing into December and January. Affordable, family-friendly pro basketball.

Winter Wonderland Drive-Thru Lights — Nov 23–Dec 31, Kensico Dam Plaza, Valhalla (nearby)

A 1.2-mile drive-through light show with a 100-foot light tunnel and a 40-foot tree. The classic Westchester holiday outing — go on a weeknight to skip the line.

More November dates

Veteran’s Day Ceremony — Wed Nov 11, Veteran’s Memorial Garden behind City Hall.

Lasdon Park Holidays on the Hill Train Show — Nov 30–Jan 5, Lasdon Park, Somers (nearby). Model trains and Santa at the Holiday Cottage.

Lumina at Harvest Moon Farm — Nov 22–Dec 30, North Salem (nearby). 500,000+ lights on an illuminated orchard trail.

December 2026 — Holiday Season

Disney’s Frozen — Dec 11–Jan 3, White Plains Performing Arts Center

The Broadway musical version of Frozen plays through the holidays. The single biggest family ticket of the season — book early.

Derek Hough — Monday, Dec 7, Westchester County Center

The Dancing with the Stars champion brings his live show to the County Center.

Untermyer Gardens Grand Holiday Illumination — Dec 7–Jan 1, Yonkers (nearby)

100,000+ lights in the historic gardens at 945 N Broadway — and it’s free. One of the best-value holiday outings in the county.

Annual holiday traditions (2026 dates TBA)

These happen every year; the city hadn’t published 2026 dates yet at press time:

City tree lighting — typically early December at Renaissance Plaza/Court Street, free.

Winter Village & Holiday Market — typically mid-December on Court Street, with vendors, igloos, and mini-golf.

New Year’s Eve Family Spectacular — Dec 31, Main & Court Streets. Live music and a midnight ball drop with fireworks, free.

More December dates

Skate with Frosty — Sun Dec 13, Ebersole Ice Rink.

Westchester Knicks home games — Dec 4, 6, 13, 27 & 29, Westchester County Center.

Every Week in White Plains

Court Street Farmers Market — Wednesdays, 8:30am–3pm (through Nov 25). Produce, baked goods, and crafts on Court Street; SNAP accepted.

Music at the Market — Wednesday afternoons alongside the farmers market.

Trivia Night — Tuesdays, 6:30pm, The White Owl Steakhouse. Team competition, up to 6 players — confirm details ahead.

Westchester Comedy Club — roughly monthly Saturdays, 8pm, Tre Angelina. NYC stand-ups, ~$28.50 cover plus food/drink minimum.

Tips for Planning Your Visit

Check the city’s own calendar. The official feed at cityofwhiteplains.org/events pulls straight from the municipal calendar and stays current.

County Center shows sell out. Freestyle Forever, Derek Hough, and the big concerts move fast — buy direct from the venue.

Holiday dates drop late. The tree lighting, Winter Village, and NYE ball drop are near-certain to return, but the city usually announces dates in November. Check back.

Parking downtown is easy. Use the city’s garages for evening events — street parking fills up fast on Oktoberfest and parade days.

Planning a trip around one of these events? Pair this calendar with our guides to the best happy hours and day trips near White Plains — and check back, because we’ll keep it updated as new 2026 dates are announced.