New York City does the holidays at full volume, and the Christmas markets are the heart of it: rows of glass-and-wood stalls in Bryant Park, an indoor artisan fair inside Grand Central Terminal, and open-air markets at Union Square and Columbus Circle. Entry to every major Manhattan market is free, which makes this one of the cheapest great days out in the city — and because New York is one of the easiest U.S. cities to reach and sleep in on points, it’s a natural points-and-miles trip for Midwest travelers. Here’s what’s confirmed for the 2026 season as of October 2026, what hasn’t been announced yet, and how to do the whole trip on miles and hotel points.

NYC Christmas markets 2026 at a glance

Market2026 datesLocationAdmission
Winter Village at Bryant ParkOct 28, 2026 – Jan 3, 2027 (shops); rink to Feb 28, 2027 — confirmedBryant Park, 42nd St & Sixth AveFree
Grand Central Holiday FairNov 9 – Dec 24, 2026 — confirmedVanderbilt Hall, Grand Central TerminalFree
Union Square Holiday MarketNot announced yet (ran Nov 13 – Dec 24 in 2025)Union Square Park, 14th StFree
Columbus Circle Holiday MarketNot announced yet (typically late Nov – late Dec)Southwest corner of Central ParkFree
Williamsburg Winter VillageWeekends in December (2026 details TBC)151 Banker St, BrooklynTicketed

Bank of America Winter Village at Bryant Park

This is the big one, and it’s already confirmed: the Winter Village kicks off its 25th season on October 28, 2026, with the Holiday Shops running through January 3, 2027, and the ice rink staying open all the way to February 28, 2027. Per Bryant Park’s official site, the shops are open Monday–Friday 11 a.m.–8 p.m. and weekends 10 a.m.–8 p.m., with more than 180 vendors selling everything from hand-poured candles to raclette and hot cider. The rink is the city’s only free-admission ice rink — you pay only if you rent skates (bring your own and you just need a free timed reservation). The Lodge, a heated rinkside food hall with two bars, runs the whole season. Time Out New York also lists a paid Club Santa experience on November 28–29 and December 5–6, and a free Santa photo spot December 14–18. If you only have time for one market, make it this one.

Grand Central Holiday Fair

Confirmed for 2026: November 9 through December 24, inside Vanderbilt Hall at Grand Central Terminal (89 E. 42nd St.). This is the one to save for a rainy or freezing day — it’s a fully indoor, roughly 6,000-square-foot artisan market, and the terminal’s constellation ceiling is worth the trip by itself. Per the terminal’s official page, hours are Monday–Saturday 10 a.m.–7 p.m. and Sunday 11 a.m.–6 p.m. through December 16, then 10 a.m.–8 p.m. daily December 17–23 and 10 a.m.–6 p.m. on Christmas Eve; it’s closed Thanksgiving Day. The 2026 vendor list skews toward jewelry, home goods and gifts — names in the directory include Craftspring (hand-felted ornaments), LoveThyBeast (pet gear) and Rachel Reinhardt Jewelry. Entry is free.

Union Square Holiday Market

Urbanspace’s Union Square market is the city’s best for actual gift shopping — more than 185 local and national vendors packed into the south end of Union Square Park. As of October 2026, 2026 dates had not been announced; last season it ran November 13 to December 24, 2025, and in recent years it has reliably opened in mid-November and closed at 4 p.m. on Christmas Eve (closed Thanksgiving Day). Expect a similar window this year, but check Urbanspace’s site before you lock in travel around it. Admission is free, and it’s an easy subway ride from Midtown on the 4/5/6, N/Q/R/W or L.

Columbus Circle Holiday Market

The prettiest setting of the bunch: vendor booths lined up at the southwest entrance to Central Park, with the park behind you and the Deutsche Bank Center across the street. Urbanspace’s official page currently says only that the market is closed for the season and “we’ll be back in 2026” — no dates yet as of October 2026. It has typically run from late November through late December. Admission is free when it’s open, and it pairs naturally with the Fifth Avenue window displays a few blocks east.

Brooklyn and beyond

Williamsburg Winter Village (151 Banker St., on the Greenpoint/Williamsburg border) is Brooklyn’s main holiday-market event, running Fridays through Sundays every weekend in December with local makers, food vendors and live music. Unlike the Manhattan markets it’s ticketed — entry was around $11.50 last season per Time Out — and full 2026 details hadn’t been posted as of October 2026, with tickets sold through Bucket Listers. One market you can cross off: the Bronx Night Market wrapped its 2026 season on October 10 and its organizers say it returns in 2027, with no holiday edition planned this winter.

Flying in on miles

New York has three airports, and nearly every U.S. mileage currency works for at least one of them. LaGuardia (LGA) is closest to Midtown and is dominated by Delta and American, so SkyMiles and AAdvantage awards from Midwest hubs like Chicago, Milwaukee, Minneapolis and Detroit are usually the play — and the rebuilt terminals are genuinely nice now. JFK is the long-haul gateway, with big Delta (SkyTeam) and American/oneworld operations plus JetBlue; it’s also where most partner-award availability shows up if you’re coming from farther afield. Newark (EWR) is United’s hub, so MileagePlus and Star Alliance miles (including Aeroplan) tend to price best there — just budget extra time and money for the trip into Manhattan. December award space tightens around the holidays, so book early and be flexible on airport.

Where to stay on points near the markets

December is peak season in New York, so award rates run high across the board — but every major program has a well-located option. All four hotels below are verified as operating and bookable as of October 2026; award prices are dynamic, so always compare the points rate against the cash rate for your dates.

  • Hyatt Grand Central New York (World of Hyatt) — directly connected to Grand Central Terminal, so the Holiday Fair is literally downstairs and Bryant Park is a five-minute walk. Hyatt still uses an award chart, but the category and any peak pricing can change, so check the current points rate on hyatt.com for your dates. Chase Ultimate Rewards transfers to Hyatt 1:1.
  • W New York – Union Square (Marriott Bonvoy) — at 201 Park Avenue South, on the northeast corner of Union Square Park, overlooking the holiday market itself. Bonvoy pricing is fully dynamic; December rates vary widely by date, so check marriott.com.
  • Martinique New York on Broadway, Curio Collection by Hilton (Hilton Honors) — a restored 1897 landmark at 49 W. 32nd St., about a 10-minute walk to Bryant Park and 15 to Union Square. Hilton awards are dynamic and vary by date; check hilton.com.
  • InterContinental New York Barclay (IHG One Rewards) — a classic 1926 hotel at 111 E. 48th St., a short walk from Grand Central and the Fifth Avenue windows. IHG award pricing is dynamic (“varies by date”); check ihg.com for your dates.

More Christmas markets on points

If holiday markets are your thing, we’ve also covered the Vienna Christmas markets for 2026 — the European originals — and Chicago’s Christkindlmarket and where to stay downtown on points, a much shorter hop for Midwest readers.

Planning to book this trip on points? Chase Ultimate Rewards points transfer 1:1 to partners including World of Hyatt and United MileagePlus — two of the most useful currencies for a New York trip (see chase.com for the current partner list). You can compare current offers and apply with our Chase referral link.
Disclosure: This is our personal Chase referral link. If you’re approved through it, we may earn a referral bonus, at no extra cost to you. You can always apply directly on Chase’s website. See our Advertising & Referral Disclosure.

Our take

NYC’s Christmas markets are genuinely worth building a trip around — free to enter, easy to string together by subway, and backed by the best city-at-Christmas atmosphere in the country. The honest downsides: weekend crowds at Bryant Park and Union Square can be shoulder-to-shoulder by early afternoon, vendor prices are New York prices (expect $15+ for a snack and a hot drink), and December hotel rates — cash or points — are among the highest of the year. Our play: go midweek in early December, hit Bryant Park at opening time on a weekday morning, save Grand Central for bad weather, and use points for the hotel so the inflated December rates hurt someone else’s wallet. And since two of the five markets hadn’t posted 2026 dates as of October 2026, double-check before booking a trip built around Union Square or Columbus Circle.

Sources

Prices, points rates, schedules and entry rules change often; confirm details with the airline, hotel or organizer before you book. Points Capital is not a financial advisor.

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