Glenview Holiday Tour
2025-12-19 13:00 - 17:00, 2025-12-26 13:00 - 17:00 (America/New_York) | Hudson River Museum, 511 Warburton Avenue, Yonkers, New York, 10701
Explore the six fully restored period rooms on a 45-minute guided tour, showcasing beautiful Christmas trees, antique ornaments and toys, and a holiday-themed tablescape. Learn about the Gilded Age holiday traditions of the Trevor family, and see the fine woodwork, furnishings, artwork, and magnificent architectural features that rank Glenview as one of the most important early Gilded Age residences open to the public. This year, the Ebony Library will showcase the Museum’s greeting card collection with reproductions and historic examples, including many by Louis Prang, who produced the first ever commercial Christmas cards in America in 1875.
Tours take place Nov. 28, 2025 through Jan. 2, 2026.

The Spirit of Christmas Past
2025-12-19 14:30 - 18:00 | The Armour-Stiner Octagon House, 45 W Clinton Ave, Irvington, NY, 10533, United States
Immerse yourself in The Octagon House and “A Christmas Carol”. Join the ladies of The Octagon House amid exquisite holiday decorations as they prepare for their Christmas festivities. After adding ornaments to the tree, checking the table settings, and practicing their carols, visitors will be treated to a performance of the Fezziwig party scene from Charles Dickens’ A Christmas Carol. Dec. 5-21, Thursdays-Sundays.

Holiday Lights Helicopter Tours
2025-12-19 16:00 - 20:30 | Wings Air Helicopters, 67 Tower Rd., West Harrison, 10604
Take your holiday to new heights with Wings Air’s Holiday Lights Helicopter Tours, featuring breathtaking views of twinkling seasonal displays in NYC and Westchester. Tours depart from Westchester County Airport through Dec. 31 (closed Dec. 25).

Lumina
2025-12-19 17:00 - 20:00, 2025-12-26 17:00 - 20:00, 2025-12-30 17:00 - 20:00 | Harvest Moon Farm & Orchard, 130 Hardscrabble Rd., North Salem, NY, 10560
At Lumina, a magical light experience at Harvest Moon Farm & Orchard in 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.

Westchester's Winter Wonderland
2025-12-19 17:00 - 21:45, 2025-12-26 17:00 - 21:45 | Kensico Dam Plaza, 1 Bronx River Parkway, Valhalla, 10595
A beloved holiday tradition, Westchester’s Winter Wonderland returns this year at Kensico Dam. Beginning Nov. 28 through Dec. 31, fans can enjoy the 1.2-mile drive-thru experience featuring dazzling light displays, including the 100-foot light tunnel and 40-foot lighted tree.

Culinary Demonstration at the Holiday Market
2025-12-20 10:00 - 14:00 | Stone Barns Center for Food & Agriculture, 630 Bedford Rd., Pocantico Hills, NY, 10591
Learn fresh takes on classic holiday dishes from Blue Hill’s chefs. Afterwards, head to the market for ingredients to make the recipes yourself. At the Holiday Market, shop for produce, meat, eggs, and cut flowers from the farm to serve on your holiday table and browse handmade goods from local vendors.

Tour & Shop Philipsburg Manor
2025-12-20 10:00 - 15:00 | Philipsburg Manor, 381 N. Broadway, Sleepy Hollow, NY, 10591
Step back to the year 1750 at Philipsburg Manor this winter. Learn about the enslaved individuals who worked on the property and whose family relationships and personal histories are revealed in primary documents. Tours through the gristmill, the dairy in the cellar of the Manor House, and more will give you a new perspective on Colonial New York. After the tour, stop by the Holiday Boutique for local finds, exclusive souvenirs, and fun holiday items.

Victorian Christmas Celebration
2025-12-20 10:00 - 15:00 | Washington Irving’s Sunnyside, 3 W. Sunnyside Ln., Irvington, NY, 10533, United States
Enjoy a festive tour of Washington Irving’s Sunnyside, all decked out in holiday finery. Sip hot chocolate or cider, enjoy a donut, and try your hand at making holiday crafts, such as paper cones and ornaments.

Tour & Shop Washington Irving's Sunnyside
2025-12-20 10:00 - 17:00 | Washington Irving’s Sunnyside, 3 W. Sunnyside Ln., Irvington, NY, 10533, United States
Learn about the man who really invented Christmas at Washington Irving’s Sunnyside, when you tour his romantic riverside cottage. Plus, see Sunnyside decorated for the holidays. Then, shop the Holiday Boutique for locally made gifts and unique souvenirs.

Holidays on the Hill
2025-12-20 10:00 - 17:00, 2025-12-27 10:00 - 17:00 | Lasdon Public Gardens, 2610 Amawalk Rd., Katonah, NY, 10536
Celebrate the season with iconic and immersive exhibits that will delight audiences of all ages. Visitors will be surrounded by the magic of the season as they stroll by colorful characters and enchanting holiday scenes. Multiple levels of tracks adorn the Lasdon Conservancy in an entirely reimagined display. Stop by to see Santa and enjoy delicious food truck fare.

Holiday Howl
2025-12-20 11:00 - 14:00 | Wolf Conservation Center, 7 Buck Run, South Salem, NY, 10590, United States
Get outside during the holidays at the Wolf Conservation Center! Learn about the mythology, biology and ecology of wolf families and discover why this season is such a magical time for packs in North America. Guests will enjoy watching gray wolves Nikai, Silas, and Kinari tear open “wolfy” presents! Guests will also potentially behold some of the WCC’s critically endangered red wolves and Mexican gray wolves. Visitors that bring a canned food item will receive a souvenir wolf photo. The program takes place on Saturdays and Sundays, Dec. 20-28, 2025.

RoCA’s Affordable Art & Pottery Bazaar
2025-12-20 11:00 - 16:00 | Rockland Center for the Arts, 27 S Greenbush Rd., West Nyack, New York, 10994, United States
Rockland Center for the Arts’ Affordable Art & Pottery Bazaar returns! December 6-20, 2025. Monday-Saturday. 11AM-4PM. Discover handmade art, pottery and gifts made by local artists. Just in time for the holidays! FREE entry. CLICK HERE for details.

Twin Star Orchards 2025 Holiday Market
2025-12-20 11:00 - 17:00, 2025-12-27 11:00 - 17:00 | Twin Star Orchards, 155 N. Ohioville Road, New Paltz, NY, 12561
Each market date will host 12 different vendors, so you can come each and every Saturday for a completely unique shopping experience. Find local delights and delicious treats for all of your gifting needs – jewelry, ceramics, candles, booze, hot sauce, honey, dog treats, skincare, greeting cards, honey, art, woodworking, and more!

Winter Solstice Celebration
2025-12-20 13:00 - 17:00 | Olana State Historic Site, 5720 State Route 9G, Hudson, NY, 12534, United States
Celebrate the changing seasons at Olana State Historic Site with a festive afternoon of free, family-friendly activities! Explore the historic house, enjoy seasonal artmaking, learn about the science of snow, and meet Hank, the miniature donkey. Highlights include a winter choir performance, storytelling, workshops, walks, a bonfire, and refreshments.

Nutcracker, Short & Sweet - Sensory Friendly Performance
2025-12-21 13:00 - 17:00 | Paramount Theater, 1008 Brown Street, Peekskill, NY, 10566, United States
The Nutcracker, Short and Sweet offers the timeless music of Tchaikovsky, engaging narration from the point of view Clara, and costumes that will delight every guest—in a setting and at a price that is perfect for audiences ages 3 and older. This one-hour performance is designed to create a welcoming and comfortable arts experience for people with autism, sensory sensitivities, or other social, learning or cognitive disabilities. Performances are at 1pm and 5pm.

Catskill Winter Solstice Stroll
2025-12-21 16:00 - 20:00 | Catskill Village, Main Street, Catskill, NY, 12414, United States
Join us in Catskill Village for the Winter Solstice Stroll, a magical celebration of the year’s longest night and the return of the sun. Wander a pedestrian-only Main Street glowing with twinkling lights, explore holiday shops and local restaurants, enjoy live music and warm refreshments, and embrace the spirit of renewal as we look ahead to 2026.

Victorian Christmas Tours
2025-12-22 10:00 - 14:30 | The Armour-Stiner Octagon House, 45 W Clinton Ave, Irvington, NY, 10533, United States
Celebrate the holiday season in Victorian splendor at The Octagon House. All rooms in the house will be decorated with wreaths, garlands, and the sparkle of ornaments on three grand Christmas trees. While exploring the colorful history of this one-of-a-kind home, visitors will see stunning examples of antique holiday décor and learn about the ways the decades of the late 19th century shaped our modern American holiday traditions. Tours are available Nov. 13 – Dec. 22.

Handmade for the Holidays
2025-12-22 10:00 - 17:00 | Clay Art Center, 40 Beech St., Port Chester, NY, 10573, United States
Browse handmade pottery, ceramic gifts, seasonal ornaments, cultural items, contemporary tableware, and sculptures.at Clay Art Center’s Handmade for the Holidays, Nov. 13-Dec. 23. During Family Days, Nov. 22 & Dec. 13, shoppers can paint an ornament, meet the artists and enjoy sweet treats.

NYC & Westchester Holiday Lights Helicopter Tour
2025-12-22 16:00 - 20:30, 2025-12-29 16:00 - 20:30 | Wings Air Helicopters, 67 Tower Rd., West Harrison, 10604
Soar through the season. 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. Tours take place Dec. 1 – 31 (closed Dec. 25).

Christmas Eve Dinner at Terrapin in Rhinebeck
2025-12-24 17:00 - 21:00 | Terrapin, 6426 Montgomery Street, Rhinebeck, NY, 12572, United States
Chef Josh Kroner’s special prix fixe Christmas Eve menu offers a diverse assortment of entrees featuring local and organic ingredients, including multiple vegetarian, vegan and wheat-free options.
Click here to see the menu and book your reservations.

The Great Holiday Train Show
2025-12-26 10:00 - 14:00, 2026-01-02 10:00 - 14:00 | Horace Greeley House, 100 King St., Chappaqua, NY, 10514
This unique holiday exhibition features something for the whole family. In addition to the trains, the rooms of the historic Horace Greeley House will be festively decorated for the season. For those who are young or young at heart, there’s a train-themed scavenger hunt, an activity room with crafts and hands-on trains, and even a mini train engine for the perfect photo op!

Westchester Comedy Club New Years Laughs
2025-12-31 19:00 | Tre Angelina, 478 Mamaroneck Ave., White Plains, NY, 10605
Laugh in the new year at Westchester Comedy Club with four professional comedians from New York City:

Paul Ollinger from The New York Comedy Festival and SiriusXM
Phil Hunt from BET and SiriusXM Radio
Ben Rosenfeld from FOX’s Laughs and his Amazon comedy special

There are two shows – one at 7pm and one at 10pm – with the same great comedians on both shows.
