What's on near Port Jervis — December 2026

December 2026 · Orange County, NY & Hudson Valley

What's on near Port Jervis — December 2026

Holiday markets, sparkling light shows, Christmas concerts, and opening day on the ski hills — December's best across Orange County, Sussex County, and the Pike County Poconos edge, all an easy drive from the Tri-State A-Frame.

Published November 1, 2026. Dates and details confirmed with the official organizers — check the linked event pages before you go. Town tree lightings and parades mostly wrap up in late November, so plan those right around the holidays.

Seasonal highlights

  • Christmas Market & Winter Wonderland at New Century — Sat Dec 5 – Sun Dec 6, 3 – 8 PM · Port Jervis (Deerpark), NY
    Minutes from the A-Frame: the 5th annual heated-tent holiday market with artisan vendors, the Radiance Light Tunnel, a tree lighting ceremony, caroling, live music, Santa visits, and kids' crafts.
  • Twinkle & Tinsel Holiday Festival — Dec 4 – 6, 10 – 24 & 26 – 31 (evenings 4:30 PM onward) · Monroe, NY
    The Hudson Valley's newest walk-through Christmas light show: millions of lights across 10 holiday zones, Santa visits, and festive food and drinks. Buy tickets online in advance.
  • Peace, Love & Lights at Bethel Woods — Nov 27 – Jan 2, select nights · Bethel, NY
    A 1.7-mile drive-through holiday light show on the historic 1969 Woodstock festival grounds — themed displays, drone light shows on select nights, and a Holiday Hub with food, drinks, and live music. Priced per carload.
  • Holiday Bricktacular at LEGOLAND New York — Every open park day Nov 27 – Jan 2 (closed Christmas Day) · Goshen, NY
    The whole resort becomes a winter wonderland: meet LEGO Santa at Holiday Headquarters, glide the Glice skating rink (free skate rentals), holiday games, and a Snowflake Build — all included with park admission.

Music & shows

  • The Nutcracker — Sat Dec 5 – Mon Dec 7 · Chester, NY
    The holiday ballet classic with a live orchestra — follow Clara through the battle with the Mouse King and the Land of Sweets at the Sugar Loaf Performing Arts Center.
  • Christmas with the Celts — Fri Dec 4 (doors 7 PM, show 8 PM) · Newton, NJ
    The beloved PBS holiday spectacular at The Newton Theatre: 14 years of sold-out touring combining Irish carols, fiery dancers, and pure holiday magic.
  • Twelve Twenty-Four Band: Trans-Siberian Orchestra Tribute — Thu Dec 10 · Chester, NY
    The nation's original TSO tribute — a high-energy, full-scale holiday rock orchestra recreating Trans-Siberian Orchestra's rock-edged Christmas spectacular.
  • Irving Berlin's White Christmas — Sat & Sun, Dec 5 – 6, 12 – 13 & 19 – 20 · Milford, PA
    The classic holiday musical on stage in a restored 1920s art-deco theater about 20 minutes from Port Jervis — two song-and-dance veterans follow a singing-sister duo.
  • Annie — Fri Dec 18 – Sat Dec 19 · Chester, NY
    Broadway's beloved "Tomorrow" musical in a professional production with a live orchestra — the perfect family holiday show in an intimate theater.
  • Top of the World: A Carpenter's Christmas Show — Sun Dec 20 (matinee, 3 PM) · Newton, NJ
    The world's premiere Carpenters tribute: an 8-piece band and an astonishing Karen Carpenter vocal resemblance perform the Christmas classics in an easy afternoon matinee at The Newton Theatre.

Markets

  • Uncork the Holidays — Shawangunk Wine Trail — Dec 5 – 6 & Dec 12, 11 AM – 5 PM · Hudson Valley, NY
    A holiday wine-trail experience: tasting flights, seasonal wine cocktails, and festive stops at four wineries per itinerary, with an Uncork Passport and complimentary tasting glass. Designated-driver tickets free.
  • Pine Bush First Friday — Fri Dec 4, 4 – 7 PM · Pine Bush, NY
    The final First Friday of the 2026 season: small-town holiday charm on Main Street with shops open late, specials, live music, and community fun.

Outdoors

  • Mountain Creek Ski Season Opening — Projected Sat Dec 5 (weather-dependent) · Vernon, NJ
    Opening weekend at the region's biggest ski area, about 25 minutes from the A-Frame — 46 runs, night skiing, and snow tubing as winter rolls in. Check the live snow report before driving over.
  • Mount Peter Ski Season Opening — Projected Sat Dec 5 (weather-dependent) · Warwick, NY
    Opening weekend at the family-friendliest ski hill around: 14 trails, tubing, and free beginner lessons every day in this valley favorite from 1936. Check the snow report before going.
  • Bear Mountain Ice Rink — Open Nov – Mar, all December · Bear Mountain, NY
    Classic outdoor ice skating in a scenic Hudson River valley park — public skating just $5 admission with rentals on site, about 45 minutes from the A-Frame.

Pick your season. We'll handle the cozy.

Catch a holiday show or stroll a Christmas market, then come home to the A-Frame — hot tub, fire pit, and the Delaware River Valley right outside the door.

Check availability

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