Westchester County Wonderland: A Comprehensive Guide for the 2025-2026 Winter Season

Posted by Tim Cotroneo
on November 11, 2025

WHITE PLAINS, N.Y. – Nov. 11, 2025 – Tucked between the Hudson River and Long Island Sound, Westchester County offers a picture-perfect winter escape just 30 miles from Manhattan. Easily accessible by Metro-North or Amtrak, this scenic stretch of the lower Hudson Valley comes alive during the colder months with festive charm and seasonal adventures. For visitors seeking both cozy indoor retreats and outdoor fun, Westchester delivers a memorable winter experience brimming with warmth and holiday spirit. Explore the top travel ideas for the 2025-2026 season, courtesy of Westchester County Tourism.

Top Things to Know:

Key Holiday/Winter Events: Lumina at Harvest Moon Farm & Orchard, Holiday Lights on the Farm at Muscoot Farm, Westchester’s Winter Wonderland, Untermyer Gardens Conservancy’s Grand Holiday Illumination, Holiday Classic Mansion Tour at Lyndhurst Mansion, Teatown’s Annual Hudson River EagleFest and family-friendly maple sugaring events throughout the County.
Hotel News: Kittle House Inn, formerly Crabtree’s Kittle House Restaurant & Inn, will reopen in early 2026.
Immersive Heritage Trails: From the Revolutionary Trail that retraces key moments from America’s founding to the African American Heritage Trail honoring powerful stories of struggle and triumph, to the Craft Beverage Trail, offering a taste of the region’s creative spirit.

Holiday Festivities & Attractions

At Lumina, a magical light experience at Harvest Moon Farm & Orchard (North Salem), visitors can stroll through a dazzling trail illuminated by over half a million lights, where festive sights include a music-synchronized Nutcracker display and a whimsical Gingerbread City brought to life by The Sugarplops—tiny, mischievous bakers hard at work behind glowing windows. Wander the sparkling paths with a cup of hot cider in hand, enjoying fresh donuts, toasty s’mores and the joyful spirit of the season. Open 21 – Dec. 30, 2025.

Celebrate the season at Holiday Lights on the Farm beginning Dec. 5, 2025 at Muscoot Farm (Katonah). Visit animals in festively decorated barns, create your own ornament, enjoy food truck bites, meet Santa and support the Friends of Muscoot fundraiser. On Nov. 23, the Holiday Gift Market on the farm welcomes shoppers with free hot beverages and a wide range of unique gifts under twinkling lights.

Westchester’s Winter Wonderland returns to Kensico Dam Plaza (Valhalla). New this year – the festivities begin with NovemberFest, a walk through light show and market taking place Nov. 21 through Nov. 23. Then, the fan-favorite drive-thru experience begins Nov. 28 and runs through Dec. 31. Cruise through a dazzling 1.2-mile holiday spectacular including the 175-foot Transporter Tunnel, a glowing string tunnel with a central stargate running along the middle. Head down Rudolph’s Runway filled with colorful light tubes, leading straight into the North Pole. Visitors can enhance the journey with the OtoCast App, which shares enchanting stories about the larger-than-life displays surrounding Westchester’s tallest holiday tree.

Celebrate the season at Untermyer Gardens Conservancy’s Grand Holiday Illumination (Yonkers), a beloved tradition featuring over 150,000 twinkling lights set to festive music from around the world. This enchanting nighttime display has become a favorite holiday event, drawing thousands of visitors each year. Opening with a dramatic lighting ceremony, this attraction is free to the public with no reservations required. Open Dec. 6, 2025 – Jan. 4, 2026.

Add historic charm to your holidays with experiences at some of Historic Hudson Valley’s most treasured sites, including Philipsburg Manor, an 18th-century estate; Washington Irving’s Sunnyside, the storybook home of the author who helped shape American holiday traditions; and Union Church of Pocantico Hills, home to stunning stained-glass windows by Matisse and Chagall. From Nov. 22–Dec. 21, enjoy special weekend tours alongside festive programming like a Paper Snowflake Making Class (Dec. 6) and Holiday Tea Party (Dec. 13) at Philipsburg Manor or a Victorian Christmas Celebration at Sunnyside (Dec. 20). At the Old Dutch Church, storyteller Jonathan Kruk brings Dickens’s A Christmas Carol to life (Dec. 13–14 and 20–21).

A Gingerbread Showcase will take place at the Wainwright House (Rye), featuring spectacular displays, hands-on workshops and themed events for all ages. Rooted in joy and generosity, this multi-day celebration supports Feeding Westchester in its mission to fight hunger across the County. The showcase runs Nov. 29 – Dec. 12, 2025.

Relive a Gilded Age holiday at Lyndhurst Mansion (Tarrytown) during the Holiday Classic Mansion Tour. Wander through ornately decorated rooms featuring dozens of Christmas trees and rarely seen estate treasures. The Holiday Makers Market returns with local artisans offering handcrafted gifts, while Dickens Tells a Christmas Carol brings the timeless tale to life in a one-hour theatrical performance. The Mansion Tour runs Nov. 28 – Dec. 28, 2025, the Holiday Makers Market takes place Nov. 28–29 and Mr. Dickens Tells a Christmas Carol performances run Dec. 14–26.

Travel back in time to the 1870s and experience the holiday season in Victorian splendor at the Armour-Stiner Octagon House’s Victorian Christmas Tour (Irvington). This unique eight-sided home is adorned with wreaths, garlands and the sparkle of antique ornaments on grand Christmas trees, offering a glimpse into 19th-century holiday traditions. Tours run Nov. 13 – Dec. 22, 2025.

Caramoor Center for Music and the Arts (Katonah) brings the season to life with festive décor and a rich lineup of December performances capturing the sights and sounds of the holidays. Events include An Amarcord Christmas vocal concert on Dec. 7, tours of the historic Rosen House and a Holiday Gift Shop Dec. 10 – 21 and Gingerbread Decorating Class for the whole family on Dec. 13.

The Glenview Holiday Tour offers a glimpse into the grandeur of the Gilded Age at the Hudson River Museum (Yonkers). Guided tours showcase six fully restored period rooms adorned with Christmas trees, antique ornaments, toys and a holiday-themed tablescape. Learn about the Trevor family’s holiday traditions while exploring the mansion’s exquisite woodwork, furnishings and architectural details. Tours begin on select dates starting Nov. 28, 2025.

Experience the newly revamped Holiday Experience at Christmas in America (Mount Vernon) – now 12,000 square feet of festive fun, free to enter. Wander dazzling holiday displays, shop seasonal décor and snap photos with Santa (on select dates). Ten percent of store proceeds benefit local nonprofits. Open Fridays and Saturdays through December.

Delight in a dazzling display of holiday lights during Holiday on the Hudson at Monteverde at Oldstone (Cortlandt Manor). This enchanting walk features themed light displays, hidden corners and romantic spots, all set against the backdrop of the Hudson River. Afterward, warm up with a holiday cocktail or hot chocolate by the fireplace in their 1920s-era bar. Runs from Nov. 22, 2025 – Jan. 4, 2026; open Wednesday through Sunday.

Kick off the holiday season with the Tarrytown & Sleepy Hollow Winter Stroll on Dec. 13, 2025. Visitors will enjoy extended shopping hours, decorated storefronts, storytelling, a free hop-on-hop-off holly jolly trolley, treats, carolers, an ugly sweater contest, live entertainment and other special events.

From charming village squares to lively indoor venues, Westchester County offers a variety of festive holiday markets perfect for seasonal shopping. The Downtown White Plains Holiday Market runs Dec. 6 – 17 and features nearly 50 artisanal vendors, firepits, live entertainment, ice sculpting, visits with Santa and a New Year’s Eve Wishing Wall. The Tarrytown Music Hall Holiday Market, running Dec. 2 – 3, brings together regional makers, live music and festive treats. The New Rochelle Holiday Market takes place from Nov. 28 – Dec. 14, adding ice skating and winter village charm, while the Holiday Market and Train Show at Nature Center at Greenburgh (Scarsdale) kicks off Nov. 15 with a sustainable outdoor market and whimsical indoor model train display running weekends through Dec. 7. Savor the season at storied landmarks and shop Philipsburg Manor and Sunnyside’s Holiday Boutiques featuring local finds, exclusive souvenirs and more, running on Saturdays and Sundays from Nov. 22 – Dec. 21. Browse handmade pottery, ceramic gifts, ornaments and more at Clay Art Center’s Handmade for the Holidays, Nov. 13 through Dec. 23. During Family Days on Nov. 22 and Dec. 13, shoppers can paint an ornament, meet the artists and enjoy sweet treats. Additionally, Windrose on Hudson (Ossining) will host Hops on Hudson’s Holiday Modern Makers Market, Dec. 12 – 14, a festive showcase and shopper’s delight highlighting Hudson Valley artists and filled with distinctive gifts.

Soar through the season with the NYC & Westchester Holiday Lights Helicopter Tour. Departing from Westchester County Airport, participants will fly over New York City and Westchester, creating unforgettable memories with friends and family. This once-in-a-lifetime opportunity showcases the breathtaking views of the iconic Manhattan skyline and familiar landmarks beautifully adorned in holiday lights. Runs Dec. 1 – 31, 2025; closed Dec. 25.

Holiday shopping meets seasonal fun at Westchester’s top malls and shopping centers. Ridge Hill and Cross County Center in Yonkers roll out festive experiences like tree and menorah lightings, photos and pet nights with Santa, breakfast events, live carolers, food truck markets and a pop-up ice rink – perfect pairings for a day of shopping and dining. The Westchester in White Plains also offers photo ops with Santa for classic holiday memories. Events run on select dates in Nov. and Dec. 2025.

Outdoor Winter Adventures

Explore Westchester’s collection of thematic trails that highlight the region’s culture, history and craft. Walk in the footsteps of patriots along the American Revolutionary Trail, with highlights like the Jacob Purdy House, Thomas Paine’s Cottage, Saint Paul’s Church, Philipsburg Manor and the John Jay Homestead. Discover powerful stories of resilience on the African American Heritage Trail, which features landmark sites celebrating the cultural and civic contributions of Black individuals. And for a flavorful detour, raise a glass along the Westchester Craft Beverage Trail – a self-guided tasting tour of standout breweries, cideries and distilleries across the County.

Lace up some skates and soak up the beauty of the winter landscape at one of the Westchester County Parks. When lakes and ponds freeze over, ice skating is allowed at Blue Mountain Reservation (Peekskill), Mountain Lakes Park (North Salem), Tibbetts Brook Park (Yonkers), Twin Lakes Park (New Rochelle), Wampus Pond (Armonk) and Wilsons Woods (Mount Vernon).
For hikers and outdoor enthusiasts alike, Teatown Lake Reservation (Ossining) has nearly 15 miles of trails open annually from dawn until dusk and also offers the community a space to learn about local wildlife. Trails – varied in level of difficulty – offer views of diverse terrain, habitats, lakes, swamps and more. Don’t miss special programming like “Snow Stories” and the “Full Moon Hike” series.

Spread your wings at Teatown’s 21st Annual Hudson River EagleFest® on Feb. 7, 2026, held at Croton Point Park (Croton-on-Hudson). Celebrate winter’s coolest visitors with live bird shows, guided eagle-spotting walks, heated tents, kids’ crafts, games, food trucks and more.

Adventurous travelers can throw on their warmest gear and head to one of Westchester’s trails, ideal for cross-country skiing and snowshoeing. One prime spot is Croton-on-Hudson’s Croton Point Park, with 508 acres on a peninsula situated alongside the Hudson River. The Kitchawan Preserve, a 208-acre natural preserve along Route 134 (Ossining), is a cross-country skier’s paradise, with the North County Trailway running across its eastern border. Cranberry Lake Preserve(White Plains) is also a great choice, while Ward Pound Ridge Reservation is the County’s largest park with well-maintained trails and varied terrain.

Tap into winter fun when maple sugaring season returns to Westchester in 2026. From January through March, enjoy family-friendly events featuring hands-on tree tapping, maple tastings and educational demonstrations that highlight the sweet science behind syrup making. Dates and locations to be announced soon.

Indoor Activities

For days when the indoors beckon, visitors can embrace their artistic side at The Pottery Factory (Mount Kisko), which offers an instructor-led paint and sip party session.

Golfers should visit the newly opened Five Iron Golf (Port Chester). Outfitted with state-of-the-art Trackman technology and high-speed cameras, visitors can use the simulator to choose their own adventure: tee it up at champion-level courses or challenge each other in one of the games. There’s something for every level of golfer.

Warm up inside at Bowlero (White Plains), which offers endless fun for all ages with 56 bowling lanes, an arcade with old-school classics like Mario Kart or Pac-Man, and a sports bar.

Explore Westchester’s vibrant museum scene this winter. The Hudson River Museum (Yonkers) blends art, history and science with over a century of cultural richness. The Hammond Museum & Japanese Stroll Garden (North Salem) offers a peaceful blend of Eastern and Western influences, featuring a bamboo grove, waterfall and koi-filled ponds. Hudson Valley MOCA (Peekskill) rounds out the experience with cutting-edge contemporary works from global artists.

Families will find hours of entertainment for the kids at LEGOLAND Discovery Center Westchester (Yonkers), the ultimate indoor LEGO® playground with endless building adventures and interactive experiences.

Let kids’ imaginations soar at the Westchester Children’s Museum (Rye). This hands-on learning space invites children to design, create and discover together. With interactive exhibits and creative exploration at every turn, it’s a place where curiosity is encouraged and learning feels like play.

For those looking for a moment of relaxation, visit Oasis Day Spa (Dobbs Ferry) to enjoy seasonal services like the Collagen Facial with Microcurrent for a lifted, glowing complexion and the Autumn Sports Trio Massage, featuring Arnica aromatherapy and Vital Body CBD cream to ease tension and prepare for winter wellness.

Seasonal Bites & Drinks

1730 Wine Bar (Mount Vernon) which offers a variety of popular and specialty wines for an international vibe representing local and regional favorites. This cozy wine bar also offers a full menu of creative dishes, comfort foods and brunch options.

Resolutions in the new year often call for healthy meals. From protein to nutrient-rich veggies and leafy greens, there are plenty of health-conscious options in the area. Try Root 2 Rise (Pleasantville), which makes each dish from scratch using organic, locally sourced, whole ingredients free of refined sugars, preservatives and seed oils. Grass Roots Kitchen (Tarrytown) offers local and seasonal plant-based favorites as well.

Nothing says perfect winter date night like a creative, cozy cocktail. Try the Whistling Rail (Bronxville) for a romantic evening of speakeasy vibes, tapas and some live jazz music.

At The Blind Pig of Westchester (White Plains), a 1930s-themed cocktail bar, don’t miss the Irish coffee – it’s a warm, whiskey-strong, slightly sweet, frothy, cream-topped caffeine boost.

Make a stop along the Westchester Craft Beverage Trail at Hardscrabble Cider (North Salem) to try their mulled cider — from apples grown on the premises — mixed with bourbon made by The Spirits Lab in Newburgh, including pure maple syrup, lemon juice and bitters. The Craft Beverage Trail showcases the region’s thriving craft beverage scene, featuring a variety of options from distilleries to craft breweries, a cidery and even a micro winery.

Find a caffeine fix to warm up on a cold winter’s day at Horsefeathers (Tarrytown) by choosing from one of their spiked coffees including Irish (with Irish whiskey), Mexican (Kahlua), Captains (Captain Morgan), Brotherhood (Frangelico), Cafe di Roma (sambuca), Cafe Almondine (amaretto), and Bailey’s Mocha (Bailey’s and chocolate).

Where to Stay

The Abbey Inn & Spa (Peekskill) invites families to a festive Breakfast with Santa on Dec. 13 from 10 a.m.–1 p.m., featuring a buffet by Apropos Restaurant, kids’ activities and a visit from Santa. For adults looking to unwind, the Stay, Sip, and Spa Package—available through Dec. 31—includes overnight accommodations at a discounted rate, two welcome mimosas, and a $200 spa credit.
Tucked along a peaceful, tree-lined road, the Kittle House Inn (Chappaqua), formerly known as Crabtree’s Kittle House Restaurant & Inn, has plans to reopen guestrooms in early 2026, offering a luxurious escape that combines the elegance of Old New York with historic charm. The restaurant will open on Nov. 19, 2025, giving visitors a head start in experiencing the property’s fine dining, celebrated wine offerings and exceptional hospitality.

The Bedford Post Inn (Bedford) is a quaint historic property dating back to the 1860s that will transport visitors to a scene from their favorite Hallmark holiday movie. It’s been restored and is home to an eight-room luxury inn, a yoga studio and two distinct restaurants. Cozy interiors are perfect for ignoring winter’s chill, including amenities such as heated bathroom floors and freestanding soaking tubs, offering a serene retreat for guests to unwind.

The Royal Regency Hotel (Yonkers) offers stylish rooms and modern amenities, providing a comfortable and upscale experience just minutes from New York. Space can be reserved for holiday gatherings, and the hotel will be hosting a brunch with Santa this season.