Just north of the city, Westchester and the Hudson Valley offer a gentler holiday season of river towns, drive-through lights and theater, an easy trip by car or Metro-North.
Lights
- Westchester’s Winter Wonderland at Kensico Dam — drive-through lights.
- Lights on Jenkins Court (Ossining) — a residential light show synced to a radio station, popular in December.
- The NYBG Holiday Train Show and Bronx Zoo are just over the line in the Bronx.
Shows
- Paramount Hudson Valley Theater (Peekskill) — “Jessica Lynn: A Very Merry Classic Christmas” on Dec 12 and a sensory-friendly “Nutcracker, Short and Sweet” on Dec 20, 2026.
- Tarrytown Music Hall — has hosted Paul Winter’s Winter Solstice Celebration around the solstice in recent years.
- Lehman Center — the Westchester Ballet Company’s Nutcracker (Bronx).
Nearby Connecticut
Stamford and Greenwich are minutes from southern Westchester: Stamford Parade Spectacular (Nov 22), Greenwich Reindeer Festival and Heights & Lights (Dec 6). See Christmas in Connecticut.
Village Traditions
River towns such as Tarrytown, Sleepy Hollow, Irvington, Rye and Bronxville hold tree lightings and holiday strolls in early December, typically announced by village governments in November.
Note: Kykuit, the Rockefeller estate, has suspended tours for 2026 during planned upgrades.
About Westchester and the Hudson Valley
Westchester County, just north of the Bronx, mixes river towns, suburbs and countryside. The Hudson Valley beyond is known for historic estates, farms and small towns that are especially charming in December. Both are easy to reach by Metro-North’s Hudson and Harlem lines.
River Towns to Visit
- Tarrytown and Sleepy Hollow: historic Main Streets, the Tarrytown Music Hall and the legend of the Headless Horseman.
- Irvington and Dobbs Ferry: Hudson River views and cozy restaurants.
- Peekskill: the Paramount Hudson Valley Theater and an arts scene.
Getting There
Metro-North’s Hudson Line follows the river from Grand Central to Tarrytown in about 40 minutes and on to Peekskill; the Harlem Line serves White Plains and Valhalla, near Kensico Dam.
Frequently Asked Questions
What is there to do in Westchester at Christmas?
Drive through Westchester’s Winter Wonderland at Kensico Dam, see a holiday show in Peekskill or Tarrytown and visit village tree lightings.
