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Top Events in the Hudson Valley | Winter ’19 – ’20 Edition

Snowy path at Stonykill farm in Dutchess County

Do you often think to yourself, “What is there to do in the Hudson Valley this weekend?” I’m here to tell you that finding things to do in Winter with the family is no easy task. People often ask me if winter is a good time to do things in the Hudson Valley and I excitedly say, “Yes, it is!”

The idea of cold scares a lot of people. However, the Hudson Valley doesn’t always get extremely cold in the Winter.

Not always. But, sometimes it does.

Lucky for you, I am native to the area and have had my fair share of NY Winters. This is why I have compiled this list of events that take place throughout the Winter and are fun for everyone.

Winter view of the lake and snow in the Hudson Valley

Added Bonus: 
I have included a list The Top 5 Places you Need to visit this Winter that you can access at the bottom of this post.

The places on the list are open throughout the year, including the winter (when most places are closed to visitors and tours). This way you can enjoy these attractions without the crowds that are often found during other times of the year.

And, best of all, these places are indoors, where you can warm up and escape the cold.

This post may contain affiliate links. Affiliate links mean that I get a little money, to help run this blog, with each purchase you make on this post. This comes at no extra cost to you. Please read my disclosure for more information.

Updated: 1/16/2020

The Best Outdoor Activities in the Hudson Valley during Winter

Check this list out and see if you find something new to do in the Hudson Valley this weekend 

Hiking in the Hudson Valley

Hiking is a big deal around these parts. There are so many beautiful areas to explore in the Hudson Valley that it’s a Hikers Paradise. Moreover, there are trails and mountains all around the region with endless possibilities of hiking on a new trail. This is also a premier destination for ice climbing.

I am NOT the outdoorsy type, so I rely on other websites, like Hudson Valley Parent, as they offer information, such as cold-weather hiking spots. They post great information about a variety of topics to help parents within the Hudson Valley.

I also live vicariously through people I follow on Instagram. They have some amazing experiences doing things I have yet to try.

While looking at their photos one can see that they have the best ticket to see the Hudson Valley from above.

Pictured Below is a beautiful picture of Carolyn and her pug, Roxy. They hike all over the Hudson Valley Region and Carolyn features her adoring pug in almost all of the photos. It’s wonderful to see all the places that Carolyn and Roxy have visited.

Instagram is a great place to find Hiking inspiration


Are you a skier, snowboarder or sledder? The better-known places in the Hudson Valley for these activities are Thunder Ridge Ski Area in Patterson, NY (Putnam Co) and Hunter Mountain in Hunter, NY (Greene Co).

There are also several others in the Hudson Valley, including Belleayre Mountain in Highmount, NY (Ulster Co), James Baird State Park in Pleasant Valley, NY (Dutchess Co) and Thomas Bull Memorial Park in Montgomery, NY (Orange Co). Check out the information online for each and see which one is a better fit for you and your family.

If you plan on attending any of these events, why not make a weekend out of it. Stay at a local hotel and take in everything the town has to offer. I love to use for my reservations. (affiliate link)

Outdoor Events in the Hudson Valley during Winter –

The Best Thing You can do at the Hudson Valley Rail Trail Winter Fest!

 The Grand Holiday Illumination

January 1st
Untermyer Gardens Conservancy, Yonkers
The Walled Garden will be lit from 4:30 p.m. until 8:00 p.m. from December 12 through the night of January 1.

First Day Hike on the Walkway over the Hudson

January 1st
Walkway over the Hudson, Poughkeepsie

Join NY State Parks & Historic Sites, Walkway Over the Hudson State Historic Park staff, and members of the #WalkwayOverTheHudson community for the annual First Day Hike on New Year’s Day.

New Year’s Day Hike

January 1st
Peach Hill Park, Poughkeepsie

A guided hike at Peach Hill Park, 32 Edgewood Dr. Poughkeepsie starting at Noon on January 1st. This hike will take us to several amazing overlooks and we will toast the New Year at the summit of Peach Hill.

First Day Hike Sterling Forest

January 1st
Lautenberg Visitor Center, Tuxedo

Come join us at Sterling Forest State Park for a First Day Hike around Sterling Lake. 

Westchester’s Winter Wonderland

January 1st – 4th
Kensico Dam Plaza – 1 Bronx River Parkway Road, Valhalla
Enjoy the Winter Wonderland Holiday Circus, FUNderland Village rides, the Santa Experience at the North Pole, ice skating, a dazzling light show, food and more!

Hike-n-Hops in the Hudson Valley

January 4th
Meet @ Peekskill Brewery

Join REI’s Outdoor School Instructors for a day to remember. Meet at the Peekskill Brewery and shuttle in the REI van to Anthony’s Nose trailhead. 

Hike in the New Year

January 4th
Teatown Reservation, Ossining

New Year’s resolutions often include getting fit—what better way to greet the New Year and engage in physical exercise than on Teatown’s trails?

Winter Full Moon Walk

January 10th
Hudson Highlands Nature Museum

Join us to celebrate the first full moon of the new decade! We’ll venture out on a moonlit hike through fields and forest to discover the sights and sounds of nature under the Wolf Moon.

Ice Skating at Ebersole

January 11th
Ebersole Ice Rink – 110 Lake Street, White Plains, NY

Public Skate Session: 1:45 – 3:15pm
Family Admission Rates: Youth: $8, Adult: $10, Senior: $5, Skate Rentals: $5

Hiking the Tri-State’s Best Places

January 11th
Bear Mountain State Park

Take this opportunity to pick your instructor’s brain about other local hikes secret waterfalls beautiful open vistas and where to go on a busy weekend. 

January Winter Weekend

January 18th & 19th
Storm King Art Center, New Windsor

Experience Storm King in the brilliant winter landscape, January 18 – 19, 11AM – 4PM.

Create Artwork Inspired by Marshlands

January 19th
Marshlands Conservancy, Rye

Create your own art to be displayed in our annual “A Different Point of View” exhibit or to take home with you. All ages are welcome. Refreshments will be served courtesy of the Friends of Marshlands Conservancy.

Family Snowshoe/Hike “Lake Maratanza Loop”

January 20th
Minnewaska State Park Preserve
Meet at Sam’s Point Visitor Center

Take a moderate hike around Lake Maratanza Loop. Call ahead for weather conditions. Snowshoe rental on site.

Scottish Weekend

January 24th – 26th
Mohonk Mountain House – 1000 Mountain Rest Rd, New Paltz, NY
The halls of the Mountain House echo with the sound of bagpipes as the Mohonk grounds transform into the highlands of Scotland! Our Scottish Weekend features award-winning musicians, concerts, workshops, Scottish history, Scotch whisky tasting, the “Address to the Haggis,” a ceilidh, Scottish country dance, bagpipe-playing, and kilt-making.

Tapping Maple Trees in the Hudson Valley is a fun activity to do during a Winter Weekend

Hyde Park Recreation Winter Fest

January 25th
59 East Market Street, Hyde Park

Celebrate the winter season with us at our annual Winter Fest! Fun activities for both in and out of the snow at Hackett Hill Park! (In the event of inclement weather, Winter Fest will be rescheduled for February 8th!)

Winter Weekends at Storm King Art Center

January 18th & 19th
February 15th & 16th
March 21st & 22nd
Storm King Art Center, New Windsor

Experience Storm King in the brilliant winter landscape.

Tracks & Traces

February 1st
Teatown Lake Reservation, Ossining

Even though it’s cold outside, many animals are busily searching for food. Follow the traces left behind and see who has been active in Teatown’s woods. For everyone.

Hudson River EagleFest

February 8th
Croton Point Park

Join us at Croton Point Park as our region’s bald eagles descend upon the Hudson River as part of their winter migration. Celebrate the return of this magnificent bird with live bird-of-prey shows, educators with viewing scopes observing wild eagles, children’s activities, food trucks, and 25+ environmental organizations — all in heated tents!

February Full Moon Hike

February 9th
Rockefeller State Park Preserve, Pleasantville

Every month we give hikers an opportunity to experience the Preserve after dark in our “Full Moon Hike” series. Please join us for this very popular and special event. Please bring a flashlight or headlamp.
Please dress according to weather conditions. Please bring water. Dogs welcome.

Tappin’ the Trees

February 9th
Muscoot Farms

Sugaring season is here again! Join us as we explain the procedures for tapping the maple trees. We will be tapping our own trees right here on the Muscoot property!

February Winter Weekend

February 16th & 17th
Storm King Art Center, New Windsor

Experience Storm King in the brilliant winter landscape, February 15-16, 11 AM – 4 PM.

Winter Wildlife Survival

February 17th
Fort Montgomery State Historic Site

How do deer, wood frogs, or even praying mantis survive the winter? Come to Fort Montgomery State Historic Site and discover how our backyard neighbors endure the winter with no clothing, grocery stores, or furnaces! 

Maple Sugaring Party

March 8th
Greenburgh Nature Center, Scarsdale

Join us as we continue the sweet tradition of maple sugaring! Bring your whole family to this popular Nature Center event and experience sap collection demonstrations, depictions of Native American and Colonial style sugaring sites, porridge making, maple crafts and treats, and more!

– Indoor Events in the Hudson Valley during Winter –

Check this list out and see if you find what to do in the Hudson Valley this weekend

School’s Out / Art’s In

January 1st & 2nd
Katonah Museum of Art – 134 Jay Street, Katonah, NY

rop in to the Learning Center on select school vacation days for unique artist-led projects where kids can make an artistic mess, experiment with new materials and practice unusual art-making
techniques all inspired by the abstract expressionist works on view.
Free to members, non-member children and adults $10.

First Friday PK: Cheers to the New Year

January 3rd
Shadows on the Hudson, Poughkeepsie
River Station Restaurant, Poughkeepsie

Shadows on the Hudson will be kicking off our celebrations with in-house dinner and drink specials for the night!
River Station Restaurant is extending its happy hour until 8:00 pm and having half-off all their appetizers!

Historic House Tour for Families

Every Saturday starting January 4th
John Jay Homestead, Katonah

What was life like 200 years ago? Compare your everyday life with the way the Jay family lived in the early 1800s.

Thematic Tour – John Jay & Ben Franklin

January 4th, 11th, 18th & 25th
John Jay Homestead, Katonah
Happy birthday Ben! Founding Father Benjamin Franklin was born in Boston on January 17, 1706. Franklin and Jay were political colleagues and personal friends.

Exploring Art Through Artists: Tony Wilkinson

January 4th
Westchester Children’s Museum, Rye

Each month, we will travel around the world to explore past and current artists, their works, and unique styles. Our special program will include hands-on art-making in the style of the featured artist. Expect a lot of color, imagination, and surprises as we create our own masterpieces!


January 4th
Trailside Museum, Cross River

Warm up at the museum with some hot cocoa and watch our feathered friends visit our feeders. Perfect for all ages!

Wine Tasting Weekend at Mohonk Mountain House

January 4th & 5th
Mohonk Mountain House, New Paltz

Join us for a culinary weekend as we explore great wines, excellent music, and delicious food!

Meet the Animals

January 5th & 10th
Wildlife Education Center @ Hudson Highlands Nature Museum

The Wildlife Education Center (WEC) is the home of many animals that can be found in our local woods, fields, ponds and rivers including, rabbits, turtles, frogs, toads, salamanders, snakes and fish.

Candlelight Tours of the Jacob Blauvelt House

January 5th & 12th
20 Zukor Road, New City

The evening is magical as the historic house is illuminated with candlelight and lanterns, fragrant with traditional sweets and decorated with festive greenery. 

Grandparent & Me Day

January 10th, February 14th, & March 13th
Mid-Hudson Children’s Museum – 75 N Water St, Poughkeepsie, NY

The second Friday of each month celebrates grandparents by offering free admission all day to grandparents when accompanied by their grandchildren.

Pajama Llama Kids Night Out

January 10th
Color Me Mine @ Palisades Center Mall

Paint a little llama, llama plate, hang out with friends, watch a movie… all in your pajamas of course! Recommended ages 5-10.

Baseball Card Show

January 10th
Westchester County Center, White Plains

All the Sports Memorabilia you could ever want is under one roof! Fun for the whole family! 

Popcorn & a Movie

January 11th
Trailside Museum, Cross River

Join us for a free screening of Tiny Giants. No movie is complete without popcorn and we will have an activity afterwards for the kids.

Howland Chamber Music Circle Classics for Kids – Fei-Fei Dong, Piano

January 11th
Howland Cultural Center, Beacon

Praised for her “bountiful gifts and passionate immersion into the music she touches” (The Plain Dealer), Chinese pianist Fei-Fei is a winner of the Concert Artists Guild Competition and a top finalist at the 14th Van Cliburn International Piano Competition.

Free Film Screening: Bird of Prey

January 11th
Ossining Public Library

World-renowned wildlife cinematographer, Neil Rettig, embarks on the most challenging assignment of his career: to find and film the rarest eagle on the planet.

Science Sunday

January 12th
Westchester Children’s Hospital, Rye

Science Sunday is an exciting and dynamic lesson that reviews a new scientific concept each month, complete with hands-on activities, awesome experiments, and fun facts presented by our very own science educator!

Picture & Prose

January 13th
Katonah Museum of Art, Katonah

Following a private tour of the Sparkling Amazons exhibition, participate in a discussion of Mary Gabriel’s critically acclaimed book, Ninth Street Women, now being developed into a television series.

Stroller Tours

January 17th
Katonah Museum of Art, Katonah

Ever wondered what life was like for women artists in New York in the 50s? Bring your baby and explore the exhibition Sparkling Amazons together with other new parents and caregivers. 

Artful Afternoons

January 17th
Katonah Museum of Art, Katonah

Looking for creative activities to do after school? Stop by the KMA on the 3rd Friday of the month for a host of fun projects and activities inspired by the exhibition Sparkling Amazons. All ages welcome.

Top Brass! West Point Band Concert Series

January 18th
West Point Cadet Chapel

Join the West Point Band as we kick off our Masterworks Concert Series with a program featuring the Concert Band Brass and Percussion under the baton of guest conductor Robert Ponto.

History of the Reservation

January 18th
Trailside Museum, Cross River

Join local historian and author Maureen Koehl to learn about the fascinating history of Ward Pound Ridge Reservation.

Animal Adventures: Warm up with Mammals

January 18th
Teatown Lake Reservation, Ossining

Come out of the cold and warm up as we see how mammals cope in winter’s frosty temperatures. For everyone.

A Walk in the Winter Woods

January 25th
Fort Montgomery State Historic Site

Take a virtual hike through the local woods! Scale icy mountains, cross frozen lakes, and make discoveries of natural interest all from the comfort of your chair! 

Hudson Valley Wingfest 13

January 25th
MJN – 14 Civic Center Plaza, Poughkeepsie

Wingfest 13 Invades the MJN Center (Formerly Mid Hudson Civic Center. This year More Restaurant-Food Trucks-Caterers Battle it Out for Wing Supremacy

Chicken wings in trays at the Hudson Valley Wing Fest

Backyard Sugaring 101

January 25th
Trailside Museum, Cross River

Learn everything you need to know to start making your own maple syrup at home, including how to identify a sugar maple and best practices for tapping and syrup production.

Good Deed of the Month Club

January 25th
Westchester Children’s Museum, Rye

Join us to hear the story Giraffes Can’t Dance by Giles Andreae where a clumsy but unique giraffe learns the importance (and fun!) of dancing to his own rhythm. You’ll even get to take home your very own dancing puppet!

Bidlestiff Family Cirkus

January 26th
Westchester Community College – Academic Arts Building Theatre, White Plains, NY

This circus adventure harkens back to the traditional American Circus that toured the country by caravan at the turn of the 20th century, while adding the artistic twist of co-founders Stephanie Monseu and Keith Nelson.

Museum Mates: Thomas Cole & The Hudson River School

January 26th
Hudson River Maritime Museum, Kingston

Learn to paint like a master! Thomas Cole, a founder of the Hudson River School of painting, was famous for his river landscapes. Children will learn basic painting techniques and create their own work of art.

Year of the Rat

January 26th
Teatown Lake Reservation, Ossining

Come meet some of the animals in the rodent family as we celebrate the Year of the Rat! For everyone.

Winter Yoga Weekend

January 31st – February 2nd
Mohonk Mountain House, New Paltz
Enjoy a weekend with Lana Heintjes who will awaken your body, clear your mind, and enliven your spirit!

Winter Hoot

January 31st – February 2nd
Ashokan Center, Olivebridge

The Winter Hoot is your source for family fun in nature, local food and crafts, and lyric-laden, foot-stomping, soul-soothing, fiddle-infused live music where the Catskills meet the Hudson River Valley.

Microscopic Discoveries

February 1st
Trailside Museum, Cross River

Use a digital microscope to take a closer look at insects, feathers and other objects we supply or bring something from home! Appropriate for all ages.

Thematic Tour – Slavery & Abolition

February 1st, 8th, 15th, 22nd, & 29th
John Jay Homestead, Katonah

The story of the Jay family, their slaves, and the way the generations of the Jays acted in response to slavery is complex. Glimpses of the past these stories give are enlightening, and in many cases, surprising.  

Fort Montgomery: Traditional Spoon Carving Workshop

February 8, 2020
Fort Montgomery

Traditional skills expert Barry Keegan will teach a coal-burned wooden spoon carving workshop. Participants will leave with their own hand- carved wooden spoon or ladle. For ages 12 and up!

Violins & Valentines by the Rivertown String Quartet

February 8th
Philipse Manor Hall State Historic Site, Yonkers

Join the Rivertown String Quartet for a Valentine’s Season Concert with Candy, Crafts and Canoodling! The Rivertown String Quartet seeks to make timeless music accessible to local communities with concerts, stories, and sometimes snacks!

Sweet & Sinful Cupcake & Wine Pairing

February 8th, 9th, 15th & 16th
Robibero Winery, New Paltz

Celebrate Valentine’s Day weekend and come discover the romance of pairing wine with some of life’s greatest pleasures. Indulge yourself with cupcakes and wine in sinful combinations.

DIA: Beacon is the premier location to visit when you're in Dutchess County, NY
what to do in hudson valley lyndhurst mansion

Annual Valentine’s Day Wine & Cheese Pairing

February 8th, 9th, 14th, 15th, & 16th
Benmarl Winery, Marlboro

Love is in the air at Benmarl Winery! Join us for our annual Valentine’s Day Wine and Cheese pairing, as we celebrate our love for local delights.

Museum Mates: Miniature Boat Building

February 16th
Hudson River Maritime Museum, Kingston

Learn the basics of model making by building your own miniature boat. Children will design and build a mini boat.

Hot Chocolate Festival

February 16th
Ashokan Center, Olivebridge

Warm up your winter with indoor and outdoor activities and several great flavors of hot chocolate!

A Mid-Summer’s Night Dream

February 28th – March 21st
Lyndhurst Mansion, Tarrytown

M&M Performing Arts Company brings a comedic, chaotic and crazy rendition of Shakespeare’s A Midsummer Night’s Dream to Lyndhurst Mansion this February and March. M&M’s production is set in Victorian dress to suit the Gothic Revival masterpiece it is performed in. 

Westchester Area Maple Open House Weekend

February 29th
Trailside Museum, Cross River

Trailside will be one of many local sugarhouses open to the public for sugaring demos and tastings. Check out Westchester Area Maple Open House Weekend on Facebook for more details!

Shakespeare Abridged

March 1st – 22nd
Lyndhurst Mansion, Tarrytown

M&M Performing Arts Company brings a madcap mash-up of all of Shakespeare’s plays to Lyndhurst in The Complete Works of William Shakespeare (abridged). Three whacky actors weave their wicked way through all of Shakespeare’s comedies, histories, and tragedies in one wild ride that will leave you breathless and helpless with laughter.

The Museum visits the Brewery

March 8th
Newburgh Brewing Company

We’ll bring a taste of the museum to Newburgh, including- historic games, a hat try on photo station, the miniature mansion and more.

Sugaring Off Party

March 14th
Trailside Museum, Cross River

Enjoy winter’s sweet rewards at this annual celebration that offers food, music and sugaring demonstrations all day. Free. 

Museum Mates: Water, Water, Everywhere

March 15th
Hudson River Museum, Kingston

Do you ever wonder what happens to the water you flush down through your toilets and sinks? This family-friendly program will demonstrate how wastewater is treated and released back into the Hudson River.

In order to enjoy all the Hudson Valley has to offer this Winter, here are a few things to keep in mind:

  • Plan ahead, but not too far in advance, as the weather can change quickly
  • Rely on local weather sites, like Hudson Valley for accurate weather forecasts
  • Visit the Hudson Valley Exposed FB Events Calendar often, so you can plan what to do on the weekends
  • Buy tickets in advance, as many of these popular events sell out quickly
  • Download the ‘Top 5 Places you Need to Visit this Winter in the Hudson Valley’ and enjoy some HV history without the crowds.
  • Come back to this post, as I continue to add events as I find them online.
  • Don’t forget that sites like Groupon also have great things listed all the time! (affiliate link)

2/25 - 2/26 Offer: Sitewide Sale: Spring Break Starts Here: Up to 20% Off Local, 10% Off Getaways, 10% Off Goods; Promo code: SAVE

My List of Top 5 Places to Visit this Winter in the Hudson Valley

Get the password for the library with my list of Top 5 places to visit this Winter in the Hudson Valley here by filling out this form:

FYI – If you’re already a subscriber, then you have access to the list in the Resource Library.

Until The Next Adventure…

Signature HVE Blog


Looking for Things to do this Winter? This list showcases both indoor and outdoor events throughout the Hudson Valley.
About Author

Jackie is the HV blogger behind Hudson Valley Exposed, featuring the hottest things to do, places to see and weekend getaways. Get information from a local who is seeing it all! She lives in the Mid-Hudson Valley Region with her hubby, kids, and doggies.

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