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Last updated: November 11, 2024

Plan your festive season in Poughkeepsie with our comprehensive guide. For Poughkeepsie natives and holiday tourists, our guide ensures everyone enjoys the festive season.

This holiday, step into a world of wonder with the Catskill Mountain Railroad Polar Express, where families can experience a magical train ride reminiscent of the beloved Christmas classic. With enchanting views and festive characters along the route, it creates lasting memories. The Poughkeepsie’s Winter Fest Market offers a cozy venue featuring local artisans, delicious treats, and holiday cheer, perfect for finding unique gifts. And the Nutcracker at Bardavon is something you definitely don’t want to miss, bringing Tchaikovsky’s timeless ballet to life in a spectacular performance. See more details on these and other fun events and activities below!

Contact information and details below.

Poughkeepsie Holiday Light Displays

What to Expect:

Dazzling drive-through light displays with festive and nostalgic themes.

Description:

The Wonderland of Lights at Dutchess County Fairgrounds features hundreds of dazzling light displays that delight the entire family. The event is open from November 28 to December 1, December 5 to 8, and nightly from December 12 to 29. Tickets are available online or at the gate, and the event supports Make-A-Wish Hudson Valley.

Where: Rhinebeck | More Info: The Wonderland of Lights at Dutchess Fairgrounds

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Poughkeepsie Holiday Markets and Shopping

What to Expect:

Free admission with vendor and exhibitor registration.

Description:

The Winter Craft Fair at the MJN Majed J. Nesheiwat Convention Center in Poughkeepsie features over 100 vendors selling handmade crafts, holiday decorations, and unique gifts. Enjoy a variety of activities including photos with Santa, holiday performances, and festive festivities.

Where: Poughkeepsie | More Info: Poughkeepsie’s Winter Fest Market

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What to Expect:

Free horse buggy rides and traditional Christmas carols.

Description:

Warwick Home for the Holidays is an annual celebration in downtown Warwick, featuring decorated shops, open house events, free refreshments, and special offers. The event includes traditional Christmas carols by the Warwick Valley Chorale and free horse buggy rides through the village.

Where: Warwick | More Info: Warwick Home for the Holidays

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Poughkeepsie Holiday Shows and Entertainment

What to Expect:

World-class ballet performance with regional artists and elaborate sets and costumes.

Description:

The Nutcracker at Bardavon features dancers from the New York City Ballet in a classic holiday event. The New Paltz Ballet Theatre brings together regional artists to create a visually stunning production. The story follows Marie as she dreams of a fierce battle between giant mice and toy soldiers, leading to a magical journey through the Land of Snow to the Kingdom of Sweets.

Where: Poughkeepsie | More Info: The Nutcracker at Bardavon

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What to Expect:

Family-friendly train ride with hot chocolate, cookies, and a silver sleigh bell.

Description:

The Catskill Mountain Railroad Polar Express is a family-friendly event where passengers relive the classic story of The Polar Express. They are whisked away on a real train to the North Pole, served hot chocolate and cookies by dancing chefs, and receive a silver sleigh bell as the first gift of Christmas. The trip includes caroling and on-board entertainment, making it an unforgettable adventure.

Where: Kingston | More Info: Catskill Mountain Railroad Polar Express

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What to Expect:

Custom-made holiday tree train with six levels.

Description:

The Great Holiday Train Show at the New Castle Historical Society features charming model trains winding through miniature landscapes in the historic Horace Greeley House. New additions include Harry Potter LEGO scenes and a custom-made holiday tree train with six levels.

Where: Chappaqua | More Info: The Great Holiday Train Show at New Castle Historical Society

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What to Expect:

Intimate, imaginative storytelling with musical accompaniment.

Description:

Master storyteller Jonathan Kruk brings Charles Dickens's "A Christmas Carol" to life at the historic Old Dutch Church in Sleepy Hollow, accompanied by musical accompaniment by Jim Keyes. This intimate, imaginative performance features over thirty characters, transforming Ebenezer Scrooge and his companions into vivid vignettes.

Where: Sleepy Hollow | More Info: Dickens’s “Christmas Carol” at Old Dutch Church

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Poughkeepsie Other Holiday Activities

What to Expect:

Historic house tours with 19th-century holiday decorations.

Description:

Explore Boscobel's Historic House Museum with an expert guide, featuring a celebrated collection of New York furniture from the Federal period, including rare examples by Duncan Phyfe. The house and grounds will be decorated for 19th-century holidays, highlighting centuries-old traditions.

Where: Garrison | More Info: Holiday House Tours at Boscobel

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What to Expect:

Meet Santa in a beautifully decorated Winter Garden setting.

Description:

Visit Santa at Boscobel, where children of all ages can meet Santa Claus in the Winter Garden. Guests can enjoy the seasonally-festooned landscape and various games and activities set out on the Forecourt.

Where: Garrison | More Info: Visit Santa at Boscobel

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What to Expect:

Candlelit holiday tour with live music and festive lights.

Description:

Boscobel House and Gardens are beautifully lit by candlelight, decorated for 19th-century holidays, and filled with live music. Enjoy mulled cider, hot chocolate, and cookies in the Carriage House while strolling through twinkling lights in the Apple Orchard, Formal Garden, and Winter Garden.

Where: Garrison | More Info: Boscobel Twilight Tours

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What to Expect:

Holiday trolley ride with festive treats and Santa visit.

Description:

Don your favorite PJs and gather at 12 Lounge for a special Adult North Pole Express trolley ride through Peekskill. Nibble on holiday treats and sip Peekskill Pride Nog while traversing the city to see beautiful holiday lights. Sing along to your favorite holiday songs and if you're good, you might even meet Santa!

Where: Peekskill | More Info: The Peekskill Trolley Company’s North Pole Express

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What to Expect:

Santa Claus lights the village Christmas tree.

Description:

The Annual Christmas Parade in Washingtonville features festive floats, decorated fire trucks, and a visit from Santa Claus, culminating in the lighting of the village Christmas tree.

Where: Washingtonville | More Info: Annual Christmas Parade

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