15 Winter Staycation Ideas for Family Fun in the Hudson Valley

From historic sites and museums to hot chocolate and overnight escapes, these staycation ideas are fun for the whole family.

Look what’s sneaking up on you again: yup, it’s winter break, that week when schools are closed, the weather isn’t welcoming, and you desperately need inspo for keeping the kids (and yourself) entertained. Before you panic, check out these 15 fab family pursuits (plus some grown-up getaway ideas) to keep everyone busy and happy during the deep midwinter.

1. Snowshoe

We’re not saying you shouldn’t queue up for a ski lift, but there’s something wonderfully easy and old-school about strapping on some snowshoes and tromping through the woods. No special skills are required, and spots like Sterling Forest State Park, Victor Constant Ski Area at West Point, and Minnewaska State Park provide the perfect terrain.

For more snowshoeing spots, check out our snowshoe guide.

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2. Get art smart

The Hudson Valley is dotted with delightful spaces where you can immerse yourself in artwork. That might mean the Hudson River Museum in Yonkers, with a winter exhibit of ceramics from the Gilded to the digital age and planetarium shows for the starry-eyed; Poughkeepsie’s Mid-Hudson Discovery Museum, a full-tilt kid-friendly option with loads of hands-on learning activities; the Katonah Museum of Art, which is hosting a young artists’ exhibition during staycation season; and Magazzino Italian Art in Cold Spring, a brilliant immersion into art and design, housed in two cool buildings.

Magazzino Italian Art
Magazzino Italian Art. Photo by Alex Hoyer.

3. Have a history lesson

Step back through the centuries at the New York State Museum in Albany with an in-depth look at Indigenous people’s 13,000 years of history in the area. Newburgh is home to General Washington’s Headquarters State Historic Site, perched high over the Hudson, where key decisions were made that impacted our nation’s birth. Historic Huguenot Street in New Paltz lets you time-travel to the early 1700s, with its seven stone houses, wigwam, and other structures. And in Troy, the Hart Cluett Museum, housed in two adjacent and impeccable 19th-century townhouses, immerses visitors in the lifestyle of that era.

Washington’s Headquarters State Historic Site
Washington’s Headquarters State Historic Site. Gilbert Stuart, Public domain, via Wikimedia Commons

4. Sip something steamy and sweet

Organize a self-guided hot chocolate tour complete with a rating system and score sheet (aroma, flavor, presentation, and marshmallow fluffiness all count). A few places to try: Larchmont’s Cocoa, a tiny pink jewel box of a candy shop, serving rich, liquid chocolate; the Maker Hotel in Hudson, with a molten cup that’s 68 percent dark chocolate; and Shokan’s Fruition Chocolate Works for an artisanal, irresistible river of chocolaty goodness.

5. Overnight in the area

Whether you want to treat the fam to a night at one of the Valley’s prettiest or coolest accommodations or just take some time off from kid duty, you’ll have plenty of options. The Hunter Houses offers a trio of chic ski cabins in the Catskills, the Home Sweet Hudson site has farmhouses and more to rent, and AutoCamp Catskills in Saugerties will rent you a luxury Airstream.

Hunter Houses
Courtesy of Hunter Houses

6. Take a seat at the table

How about dinner and a show—that is, taking the fam out for hibachi? Typically, these meals involve sitting around a grill table as chefs slice, dice, sauté, and flip shrimp tails into their toques; perfect for making a staycation feel festive. Try SOTO Sushi & Hibachi in Baldwin Place, Izumi in Wappingers Falls, Golden Ginza in Kingston, or Iron Chef Hibachi & Asian Fusion in Newburgh and other locations.

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7. Unlock your creativity

Go beyond appreciating art to making some. Treat kids to a drop-in session at Rhinebeck’s Hudson Valley Pottery or check out Port Chester’s Clay Art Center’s family wheel class so everyone can get hands-on with ceramics. Or sign your teen up for a felting or watercolor class at Hudson Valley Atelier (locations vary), or try another kind of creative pursuit: circus arts at Blooming Grove’s Body Art Barn.

8. Walk this way

With thermal layers and thick socks, winter hiking can be a great outing. Experience the hush of a silent trail at the Greenport Conservation Area, just north of Hudson, with a short hike to an overlook with incredible Hudson River and Catskills views. Rye’s Marshlands Conservancy packs marshland, forest, meadow, and shoreline trails into its 147 acres. Or, for an extra dramatic view, try a different kind of trek: one across the Walkway Over the Hudson that runs between Poughkeepsie and Highland, and stand 212 feet above the river.

Walkway Over the Hudson
Walkway Over the Hudson. Courtesy of Dutchess Tourism.

9. Climb a wall

Literally. Indoor rock climbing is fun, challenging, and physical, which is perfect when the weather outside is gloomy. Courses are typically customized for different skill levels, whether you have a beginner in the family or one who could rival the speedsters at the Paris Olympics. Try Gravity Vault Indoor Rock Climbing in Poughkeepsie or Movement in Valhalla.

rock climbing
Courtesy of Gravity Vault

10. Burn off some energy

Kids run wild at indoor play spaces, no matter what the weather is outside. So consider: Bounce (trampolines, roller skating, mini golf, laser tag) in Poughkeepsie; Wood’n Wheel (roller skating, laser tag, bumper cars, inflatable slides, arcade games) in Ulster Park; Fun Max Adventure Park (ninja course, foam pits, VR experiences) in Wappingers Falls; and Play Haven, a two-story farmhouse with blocks, art activities, and creative play in Kingston.

11. Drink to that

Sometimes, parents need a little R&R (respite and recovery) from their staycation duties of showing their kids a good time. Head out to a tasting room for a glass of something grown-up and delicious. Consider C. Cassis in Rhinebeck, which offers cocktails mixing their signature blackcurrant liqueur in inventive ways, plus nibbles. At Neverstill’s tasting room in Hudson, you can sip their eponymous wines and other NY-local options. Not too far away on Warren Street, Bar Bene serves up warming mulled wine in cold weather. And Brunette, with its lush, high-ceilinged space in Kingston, has a fab selection of vintages.

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C. Cassis
C. Cassis. Photo by Winona Barton-Ballentine.

12. Pass the popcorn

Short, chilly days and movies were made for each other. A couple of hours of bigscreen entertainment can be a brilliant way to escape the winter doldrums. Visit a sweet old movie house like Rhinebeck’s Starr Cinema, Saugerties’ Orpheum Theater, the Rosendale Theatre, The Beacon, and Millerton’s Moviehouse.

popcorn
Adobe Stock / Africa Studio

A good flick at a vintage movie house is the ticket to indoor staycation fun.

13. Glide on

Lace up those skates, and step onto an ice-skating rink. Among your indoor options are Rye Playland’s Art Deco Ice Casino or Elmsford’s Westchester Skating Academy and Newburgh’s IceTime Sports Complex. For those who prefer to skate outdoors, it’s hard to beat the Bear Mountain Ice Rink, with glorious views of the Hudson Highlands. Or get the best of indoors and out with a day-pass skating session at Mohonk Mountain House’s palatial covered skating pavilion.

Mohonk Mountain House
Mohonk Mountain House. Courtesy of Mohonk Mountain House.

A staycation can be as active as a vacation with play spaces, ice rinks and mansion tours at your fingertips.

14. Take a house tour

The Hudson Valley is known for its mansions, and a staycation is a perfect excuse to explore them. Kykuit, the Rockefeller estate in Sleepy Hollow, is a true jaw-dropper with an exceptional art collection. Hyde Park’s Springwood, FDR’s home, will charm with its references to Fala, the President’s terrier, and Olana, artist Frederic Church’s Hudson homestead, dazzles with its majestic hilltop location and its moody Moorish furnishings.

Olana
Olana. Photo by Stan Ries.

15. Dine out in style

If you’ve been spending a lot of time around the house in pjs, getting dressed up for dinner can serve as a posh exclamation point for a stay-at-home week. You might cozy up at Clare de Boer’s Stissing House, a circa-1782 building in Pine Plains with obsession-inducing roasted chicken and heavenly coconut cake. Foxfire Mountain House in Mt. Tremper offers a singular menu—where else will you find bison tartare and roasted bone marrow? And Rhinebeck’s sleek Pretty to Think So delivers indulgent dishes like caviar frites and blue oyster risotto.

Stissing House
Stissing House. Photo by Chris Mottalini.

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