The Hudson Valley truly shines during the holiday season. From charming Black Friday shopping, Small Business Saturday and shopping local, to Christmas makers markets to dazzling light shows and cozy winter festivities, there’s something magical for everyone. Whether you’re planning a weekend getaway or looking for family-friendly things to do, here’s your ultimate guide to 2025 Hudson Valley holiday events — organized by month and region.

November 2025

🎁 November 2025: Holiday Kick-Off & Black Friday Weekend in the Hudson Valley

🏠 Christkindlmarkt at Germania of Poughkeepsie (Poughkeepsie, NY)

Dates: November 21–22, 2025
Kick off the holidays with authentic German food, homemade baked goods, and local artisan vendors. Enjoy indoor dining and a heated vendor tent while you shop for unique holiday gifts.
🕓 Open Nov 21 (4–9 p.m.) & Nov 22 (10 a.m.–6 p.m.)

🎁 Hudson Valley Hullabaloo - Holiday Market - November 22 (10am-5pm) & November 23, 2025 (10am - 4pm)

75 Makers, Artists, and Designers Festive Holiday Shopping - $2/Cash Entry - Kids 12 and Under Free

🛍️ BIG Holiday Vendor & Craft Show – HVSPCA (New Windsor, NY)

Date: November 22, 2025
Shop local artisans, enjoy food trucks, music, and festive fun at the Hudson Valley SPCA’s holiday market.
📸 Don’t miss “Santa Paws” for pet and family photos with Santa!

🍎 Twin Star Orchards Holiday Market (New Paltz, NY)

Dates: November 22 & 29; December 6, 13, 20
This farm-based pop-up market features local produce, cider, and handmade gifts. Each weekend brings new artisan vendors and delicious seasonal bites.

🎨 Hudson Valley Art Market at Locust Grove (Poughkeepsie, NY)

Dates: November 28–30, 2025
Support local artists and makers at this fine art and handmade goods market — now in its 11th year.

🧵 Basilica Farm & Flea Holiday Market (Hudson, NY)

Dates: November 28–30, 2025
A “holiday market / anti-Black Friday” event celebrating over 120 Hudson Valley artisans, food vendors, and makers inside the iconic Basilica Hudson.

🎁 Holiday Market at Bethel Woods Center for the Arts (Bethel, NY)

Dates: November 28–30, 2025
One of the region’s largest holiday markets featuring 75+ local artisans and specialty food makers.
🎟️ Free admission & parking.

🎁 53rd Annual DCCF Holiday Craft Fair (Dutchess Community College, NY)

Dates: November 29–30, 2025
A juried craft fair with 100+ artists showcasing handmade jewelry, ceramics, fine art, ornaments, and more. Shuttle service connects both event halls.

🎄Port Jervis Christkindlmarkt (Port Jervis, NY)

Dates: November 30th, 2025 - 10am -4pm

The Port Jervis Christkindlmarkt is an annual, German-style Christmas market held in historic downtown Port Jervis, NY, featuring local vendors, food, live entertainment, and family-friendly activities.

🎄 December 2025: Holiday Markets, Santa Events & Festive Fun

🖼️ Artists & Makers Holiday Market (Kingston, NY)

Dates: December 6–7, 2025
This European-inspired market features regional artists offering affordable, one-of-a-kind gifts in a warm, festive atmosphere.

🎄 Trucks N’ Trees (Warwick, NY)

Dates: December 6–7, 2025
Grab a Christmas tree, enjoy local food trucks (all put on by Warwick Food Truck Festival), and shop seasonal goods at this small-town favorite.

🏺 Garrison Art Center Holiday Pottery Show & Sale (Garrison, NY)

Dates: December 6–14, 2025, closed Monday, December 8th
Find handcrafted ceramics, jewelry, and artisan gifts made by 30+ regional artists.

❄️ Sleepy Hollow/Tarrytown Winter Stroll (Sleepy Hollow/Tarrytown, NY)

Dates: December 13th, 2025 - 2pm - 6pm

Take a stroll or hop-on-and-off FREE jolly trolleys to visit participating businesses in both Villages

Visit The Bucci Real Estate Team to enter their “Ugly Sweater” contest!
Visit and vote for your favorite festive storefront decorations
Enjoy extended shopping hours, delicious treats, special discounts and festive entertainment!
Get into the holiday spirit with carolers, dancers, kid’s activities & performances!

🍻 Drowned Lands Sip & Shop (Warwick, NY)

Dates: December 13–14, 2025
Sip hot cocoa or craft beer while browsing local vendors and makers in a cozy, festive setting.

🏰 Lyndhurst Mansion Holiday Classic Tour (Tarrytown, NY)

Dates: November 30 – December 28, 2025
Tour the historic Lyndhurst Mansion decked out in lavish holiday décor. Includes access to the Holiday Market and themed photo ops.

✨ Ongoing Holiday Lights & Multi-Month Events (November–December)

🕯️ Twilight Tour: A Jane Austen Holiday – Boscobel House & Gardens (Garrison, NY)

Dates: Fridays & Saturdays, November 28 – December 13
Step into a candlelit 19th-century mansion inspired by Jane Austen’s world. Enjoy live piano music, Regency-era décor, and festive greenery — a must-see Hudson Valley holiday tradition.

💡 ERDAJT’s Christmas Light Display (LaGrangeville, NY)

Dates: November 28 – December 28, 2025
Recognized by the Guinness Book of World Records for the most Christmas lights on a residential property — over 600,000 synchronized lights!

🎄Peace, Love Lights - Bethel Woods Center for the Arts (Bethel, NY)

Dates: November 28 - December 28, 2025

Starting on Black Friday, experience the sparkling brilliance of our light show, winding through 1.7 miles of the beautiful Bethel Woods grounds from the comfort of your car. Just turn off your headlights and follow the magical glow.

Please Note: Dates, times and location are subject to change at any time.

Regular Prices
Standard Vehicle: $27

Sullivan 180 Walk-Thru Monday takes place every Monday from 5 PM - 9 PM (Last Entry 7:30 PM). No drive-thru will occur on Mondays.

🌌 Lumina Magical Lights at Harvest Moon Farm & Orchard (North Salem, NY)

Dates: Nov 21–22, 26, 28–30; Dec 4–23, 26–30, 2025
Journey through illuminated tunnels, enjoy music-synced light shows, and capture moments at interactive photo ops.
☕ Grab hot drinks and light-up wands while you explore this enchanting, family-friendly experience.

🐴 Dogwood Acres Family Farm – Winter Wonderland (Warwick, NY)

Dates: November 28 – December 30, 2025
Enjoy festive light displays, farm animals, and holiday photo ops at this charming family farm.

❄️ A Frosty Fest (Ulster Park, NY)

Dates: Weekends from November 28 – December 30, 2025
Choose from drive-through or walk-through holiday light experiences featuring music, costumed characters, and themed attractions for all ages.

September and October in the Hudson Valley are packed with crisp air, colorful leaves, and some of the region’s most iconic celebrations. From Oktoberfest steins and grape stomping to garlic feasts, apple picking, and lantern-lit nights, there’s no shortage of ways to embrace the season. Whether you’re looking for family-friendly fun, local food and drink, or arts and culture, the Hudson Valley has a fall festival for everyone.

Here’s your guide to the can’t-miss events this September and October 2025

September 2025

September 6–7 – Oktoberfest – Germania Festival Grounds, Poughkeepsie, NY
Raise a stein and enjoy live music, traditional German food, and family-friendly festivities at this classic Oktoberfest celebration.

September 6–7 – Hudson Valley Wine & Food Festival – Rhinebeck, NY
Over 300 vendors showcase New York wineries, cideries, distilleries, breweries, gourmet specialty foods, as well as fine arts and crafts.

September 12–November 16 – Great Jack O’Lantern Blaze – Van Cortlandt Manor, Croton-on-Hudson, NY
Experience thousands of illuminated pumpkins in creative displays, perfect for a magical autumn evening stroll.

September 20 – Skywalk Arts Festival & Rip Van Winkle 90th Anniversary – Rip Van Winkle Bridge, Catskills, NY
Celebrate local artists and the iconic Rip Van Winkle story with live art, crafts, and cultural performances.

September 20–21 – Moon Festival – Port Jervis, NY
Honor the harvest season with lanterns, music, and community festivities at this vibrant celebration of moonlight and tradition.

September 21 – Sleepy Hollow Street Fair – Sleepy Hollow, NY
Featuring over 145 arts and crafts vendors, food, and local shops, plus entertainment for the whole family.

September 20–21 – Benmarl Harvest Grape Stomping Festival – Marlboro, NY
Get hands-on in the winemaking tradition with grape stomping, tastings, and live entertainment.

September 27–28 – Hudson Valley Garlic Festival – Saugerties, NY
Savor garlic-inspired dishes, local crafts, and live music at this flavorful celebration of one of the Hudson Valley’s most beloved crops.

October 2025

October 4 – Town of Tuxedo Fall Festival – Tuxedo Park, NY
A day of seasonal fun featuring crafts, pumpkins, face painting, hayrides, food trucks, and community activities.

October 4–5 – Hudson Valley Apple Festival (Barton Orchards) – Poughquag, NY
Pick fresh apples, enjoy hayrides, and savor apple-themed treats at this family-friendly harvest celebration.

October 4–5 – Handcrafted Oktoberfest – Dutchess County Fairgrounds, Rhinebeck, NY
Celebrate artisanal foods, local beers, and Oktoberfest traditions in a lively, handcrafted setting.

October 5 – Warwick Applefest – Warwick, NY
A beloved annual tradition featuring apple tastings, live music, and fall activities for all ages.

October 10–12 – O+ Festival – Kingston, NY
Experience a unique blend of art, music, and community wellness at this creative cultural festival.

October 11–13 – Harvest Festival Weekend (Barton Orchards) – Poughquag, NY
Enjoy seasonal produce, pumpkin picking, and family-friendly farm fun over a festive weekend.

October 11–12 – Sugar Loaf Fall Festival – Sugar Loaf, NY
Discover local artisans, live music, and seasonal crafts in the charming village of Sugar Loaf. Trick-or-treating for kids included!

October 11 – Coxsackie Fall Festival at The Grange – Coxsackie, NY
Celebrate autumn with live entertainment, local vendors, and community activities in historic Coxsackie.

October 12 – SUP Witches of Sleepy Hollow Festival – Kingsland Point Park, Sleepy Hollow, NY
A spooky and fun event combining paddleboarding on the Hudson with a Halloween twist.

October 12 – Nyack Famous Street Fair – Downtown Nyack, NY
Featuring over 300 exhibitors across four states with arts & crafts, home decor, unique gifts, food, and entertainment.

October 18–19 – Hudson Valley Sheep & Wool Festival – Rhinebeck, NY
Meet local shepherds, explore fiber arts, and enjoy hands-on demonstrations at this beloved agricultural and craft festival.

October 19 – Rosendale International Pickle Festival – Rosendale, NY
With over 100 vendors, this festival features pickle-inspired eats, baked goods, crafts, and the famous Pickle Triathlon with contests and games.

October 26 – Nanuet Fall Festival – Lake Nanuet Park, Nanuet, NY
A family-friendly event with pumpkin decorating, live music, vendor booths, and a Trunk or Treat celebration.

Ongoing Fall Events

September & October – Fall Harvest Festivals – Fishkill Farms, Fishkill, NY
Pick apples, taste cider, and enjoy seasonal treats at this scenic farm throughout the fall.

September & October – Harvest Festivals at Bethel Woods – Bethel, NY
Enjoy corn mazes, hayrides, farm and craft vendors, and food trucks.

Through October 4 – New York Renaissance Faire – Tuxedo Park, NY
Step back in time with costumed performers, jousting, and artisanal food at this lively Renaissance Faire.

September 12–November 16 – Great Jack O’Lantern Blaze – Croton-on-Hudson, NY
A magical pumpkin spectacle lighting up the fall nights with intricate designs and themed displays.

September 19–November 1 – Mystic Moon at Harvest Moon Farm – North Salem, NY
Experience illuminated gardens, mystical installations, and seasonal enchantment at this evening festival.

Plan Your Hudson Valley Fall Adventure

With so many festivals and seasonal events, September and October are the perfect months to experience the magic of fall in the Hudson Valley. Whether you’re looking for apple orchards, cultural celebrations, or family fun, there’s a festival waiting for you. Grab your calendar, pack your sweater, and get ready to make unforgettable autumn memories.

🎄 The Ultimate Guide to 2025 Holiday Events & Christmas Markets and Light Displays in the Hudson Valley