Cold-weather hiking spots in the Hudson Valley

Take a walk in an outdoor wonderland at these great hiking spots

Snow, kids playing in the snow, cold weather hiking

I recommend some of my favorite area spots to hike, so that you can enjoy walking in the Hudson Valley’s own winter wonderlands:

Bear Mountain State Park (Orange County)
Hike up the mountain or on easy roads around the lake and enjoy resort amenities like a carousel, zoo, and ice skating rink.

Clermont State Historic Site (Columbia County)
Stop by the historic house, enjoy the views of the Hudson River, and explore the grounds, from formal gardens to carriage roads to steep hills leading to the river.

Delaware & Hudson Canal Linear Park (Sullivan County)
Step into the history of this 45-acre park, and travel along three and a half miles of trail that passes through the remains of original locks, drydock, and waste weirs.

Dutchess County Rail Trail (Dutchess County)
Enjoy this 13 mile trail which runs from the old train depot in Hopewell Junction to the Walkway Over The Hudson in Poughkeepsie. Check out woodland views on your journey to the Walkway.

Esopus Meadows Preserve (Ulster County)
Look for herons and swans, skip rocks on the river, and walk the network of easy trails; my favorite leads to a pedestrian-and boat-access-only beach with a great view of the lighthouse.

Fallsburg O&W Rail Trail (Sullivan County)
Walk these level trails, and stop by the visitor’s center for an exhibit on historical trains.

Franny Reese Park (Ulster County)
Enjoy a stunning view of the Walkway Over the Hudson and an impressive bluff perched above the western shores of the Hudson.

Heritage Trail Entrances (Orange County)
Follow the former Erie Railroad as it winds past historic graveyards, onion farms, a wildlife sanctuary, and the villages of Monroe, Chester, and Goshen.

Manitoga: The Russel Wright Center (Putnam County)
Go on an adventure through the forest at the home of Russel Wright, American home-furnishing designer. The 75-acre landscape has links to the Appalachian Trail that even your dog can enjoy.

Minnewaska State Park Preserve (Ulster County)
Stroll around the lake and watch for hawks flying beneath you on these steep carriage trails lined with craggy rocks.

Mohonk Preserve (Ulster County)
Explore the extensive network of carriage roads and trails, or stay close to the visitor’s center and check out the children’s forest and indoor educational facilities.

Mills Norrie State Park (Dutchess County)
Hike along the Hudson River and enjoy the breathtaking views, and make sure to stop at the Mill's Mansion- an elegant country estate built during America's Gilded Age.

Poet’s Walk (Dutchess County)
Follow easy trails to the gazebo and add on loops to the summer house and flagpole lot, and see why these views inspired nineteenth-century writers.

Roosevelt Farm Lane Trail (Dutchess County)
Hike these packed-gravel trails connecting the historic Roosevelt sites and watch for birds and wildlife along the way.

Wallkill Valley Rail Trail (Ulster County)
Enjoy hiking, biking, cross country skiing, and other outdoor recreation at this linear park that was transformed from an abandoned Railroad in 1983.

Harrier Hill Park (Columbia County)
A short, universally accessible trail leads from the parking area past a farm pond to the pavilion. The 2-mile Stockport-Greenport Trail, which traverses a dramatic ravine, connects with additional hiking opportunities in the Greenport Conservation Area.

Hyde Park Trail River Overlook (Dutchess County)
The relatively easy walk passes through a peaceful, wooded ravine and crosses a small but pleasantly noisy stream before ending at the overlook affording magnificent views of the Hudson River and Esopus Island.

Fishkill Ridge (Dutchess County)
Magnificent views of the Hudson Highlands — and even Manhattan's skyline — provide ample compensation for the rigors of hiking through this rugged terrain. The 8.3 miles of trails at Fishkill Ridge are strenuous. There are some serious uphill climbs and several rock scrambles, as well as tricky descents. For the truly adventurous, there are connections to additional trails in Scenic Hudson's Mount Beacon Park and Hudson Highlands State Park.

Esty & Hellie Stowell Trailhead at Storm King Mountain (Orange County)
The trailhead provides access to Storm King State Park and over 11 miles of challenging trails—steep, narrow and rocky—leading to dramatic summit views of the Hudson River and Highlands.

Illinois Mountain
 (Ulster County)
With trails that ramble through rocky switchbacks, contouring up the ridge to reveal hidden treasures such as wetland habitats, rocky outcroppings and native ferns aplenty; it has been said that this site is not about the destination but the journey itself.

Updated 11/3/2023

Other articles by HVP Top Lists

  • Best places to ride a horse in the Hudson Valley

    Delight the horse lover in your family

    Riding lessons and trail rides are a great way to enjoy nature in the Hudson Valley read more »
  • Favorite Hudson Valley Playgrounds

    Our favorite playgrounds with a checklist for parents on playground safety

    The Hudson Valley provides some of the most beautiful, fun and safe playgrounds for your children. Some of them are hidden gems, and we want to share them with you! Also, check out our playground safety check list. read more »
  • Indoor Play Spots

    We've picked the best play spots in the Hudson Valley that your family is sure to love!

    Weather can be unexpected and ruin an outdoor play date. These indoor playgrounds are great spots to save the day and let your children's imaginations run wild! read more »
  • Hudson Valley Sweet Shops

    Top places to grab a sweet treat, birthday cake and more

    Need a birthday cake? A sweet cookie reward for a great report card? Or just a break to indulge in a sweet treat? Find out where the favorite bakeries and candy shops are in the Hudson Valley. read more »
  • Indoor spots for teens to play

    Older kids need to have some play time too

    Teens need places to go that aren't lame and won't bore them to tears. We have the best in the Valley listed just for you. read more »
  • Best places to bowl in the Hudson Valley

    Take the family and have a ball

    Bowling is one of America's favorite, family-friendly past times. read more »
  • Hudson Valley Winter Farm Markets

    The very best in local, fresh produce and more

    If you're missing the summer farm markets, have no fear. You can still get fresh produce, eggs, and meat. Plus, you will find pastries, homemade products, jams, jellies, honey, cider, and lots more. read more »
  • Hudson Valley coffee shops

    Drool worthy treats and a great cup of joe

    The Hudson Valley is brimming with eclectic, upscale, casual and family-friendly destinations in every crevice of the Valley. Here we have listed some many of our readers' favorites in Dutchess, Ulster, Sullivan and Orange Counties. read more »
  • Best of children's consignment stores

    Local consignment shops...a great alternative

    Looking for good deals? Consignment shops may be the way to go. read more »
  • Hudson Valley Museums your kids will love

    An educational and fun day trip perfect for the family!

    A trip to a museum can be an adventurous learning experience for everyone in the family. The Hudson Valley is home to many museums, historic sites, and learning centers—these are just a few to get you started. read more »