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Millbrook Vineyards & Winery, Millbrook
Crawl through mud. Climb over tires. Overcome a wall, roar, and make a 5k dash through the vineyard…then sit down and sip some excellent Valley vintages. That’s the scene at Vino & the Beasts, a 21-and-over obstacle course designed to be intoxicatingly fun for everyone involved. Up for the challenge? This event is annual (it was on August 26 this year), so raise your glass and start training, now!
Sunflower Art Studios, Gardiner
This 501(c)3 non-profit organization succeeds with soaring marks at meeting its goal: to provide financially accessible art education, and a community-oriented, supportive space to come and create. Classes include everything from drawing, painting, and sculpture, to rug- and puppet-making and even yoga, all designed to nourish you and your kids’ creative spark. Studio time varies; offering prescheduled programs, rentals, special events, and a pop-up artisan shop that features imaginative wares without the need to scout out or wait for craft shows. But what really makes this the place to go is the environment, which is always warm and welcoming.
The Spotty Dog Books & Ale, Hudson
Head to trivia night here and you’ll get questions of all kinds — music, literature, current events, history, etc — fired at you and up to three other teammates in what the barkeeps refer to as an epic, “all-nerd throwdown.” At stake? A free bar tab and your name on the board. The challenge is so popular, it’s been able to go down bi-weekly since 2006. But what else do you expect from a one-of-a-kind library pub set in an 1890s firehouse-turned-bookshop?
Windham Mountain Bike Park, Windham
The Catskill Mountain terrain has been developed by world-renowned trail designers to give riders of all levels something to get stoked about. You can experience the ultimate downhill riding experience, pedal your heart out in a mountain bike race, or try out the longest jump trail on the East Coast. Need more proof that this spot is king of the hill? The trail is frequently visited by professional riders from all over the world and will be hosting the UCI World Cup Mountain Bike Races in 2019.
Bethel Woods Center for the Arts, Bethel
Located at the historic site of the 1969 Woodstock Festival, Bethel Woods hosts some of today’s biggest performers in a grand, 800-acre, outdoor amphitheater. You can get up close to your favorite artists in a seat near the Pavilion Stage or bring a blanket and prepare for out-of-this-world entertainment while sprawled out on the lawn. The list is always diverse, and this year’s lineup included Rod Stewart with Cyndi Lauper, Kings of Leon, Goo Goo Dolls, and Zac Brown Band.
The Create Workspace, Poughkeepsie
The craft studio at Poughkidsie has been rebranded into The Create Workspace, and we approve. Here, adults can take part in art classes or events such as trivia nights, sewing/quilting, and wine tastings, while their child is also taking a class there or playing in the Poughkidsie Village. The ample number of interior windows throughout the space offers plenty of visibility to keep an eye on your little one. It is the ideal place for every member of the family to release the imagination.
Jericho Drive-In, Glenmont
After 60 years in the movie biz, this retro drive-in continues to be a memorable destination for feature films to please your whole crew. Head here on any weekend and you’ll discover an ample lot, a double-header of new releases (at reasonable ticket prices), and a projection system just as good as any indoor Megaplex. A snack bar offers up the usual stuff, but an on-site ice cream shop, Twist, takes the whole experience up a notch with artisanal scoops, 20 types of specialty soft serve, and Italian ices.
Hunter Mountain, Hunter
While Hunter Mountain is the place for skiers and snowboarders when the temperature drops, the warm-weather months are, well, hot. A robust event list is packed with live music, dancing, delicious food and drink festivities, and even plenty of activities for the kids — all put on by highly professional organizers and planners, and presented against a backdrop of pristine Valley surroundings. Some of our annual favorites are the Taste of Country Music Festival, Mountain Jam, and Oktoberfest; how about you?
Storm King Adventure Tours, Cornwall-on-Hudson
“Adventure” is not just part of their name for show: Explore marshes, marvel at the sunset, take a combination water and walking tour of Bannerman Castle, and more onboard a boat you book with these locally loved tours. What’s more, lessons are given before heading out and all tours are guided, ensuring first-timers and expert paddlers alike will find themselves at home on the Hudson while out and about with this outgoing troop.
Mountain Valley Guides, Cornwall-on-Hudson
Imagine your best canine companion bouncing on the front of a kayak (don’t worry, she’ll wear a life vest) across the Hudson River, her mouth open, tongue happily flapping in the breeze. You’ll be manning the paddle under the guidance of one of Mountain Valley Guides experts, on your way to a river beach where you can frolic together in one irresistibly corny afternoon of puppy love. Yes, Mountain Valley Guides, of Cornwall-on-Hudson, can actually make this, and equally Fido-focused memories, happen.
Cedar Lakes Estate
Cedar Lakes Estate, Port Jervis
Five hundred acres of pristine lakes, lawns, and cedar forests encompass this venue, available for weddings, corporate retreats, or any event you want to shape into something truly special. Quaint cottages and cabin accommodations adorned with modern designs dot the photo-ready property, private chefs prepare farm-to-table meals, and outdoor adventure activities — like a waterfront zipline — take your day or overnight stay to the next level.
Five Rivers Environmental Education Center, Delmar
With 450 acres of fields, forests, trails, and wetlands Five Rivers Environmental Education Center offers a rich variety of tours and guided school lessons that promote awareness, knowledge, and appreciation of New York State’s environment. More than 10 miles of trails help foster discovery and physical fitness through wholesome outdoor recreation. You can take a guided tour or explore the grounds on your own, and meet turtles, frogs, and grassland bird species on your trek.
Addition to a Main Street
The Beacon Hotel, Beacon
For years Beacon has been hailed as the new Brooklyn, but now it has finally arrived, with the opening of a boutique hotel. Alla Kormilitsyna, a luxury townhome renovator, bought Beacon’s oldest continuously running hotel, gutted it, and turned this historic 1877 building into a warm, stylish bar, restaurant and 12-room boutique hotel. Come in for a drink at the bar and watch the goings-on along Main Street, have a romantic dinner in the back restaurant or garden, or book the whole place (rooms and all) for your event.
B&B for Animal Lovers
The Homestead, Saugerties
Animal-lovers are in good company here, where photographic portraits of the rescued residents at the Catskill Animal Sanctuary are just the beginning of how the folks in charge are furry friend-friendly: your stay offers freedom to roam the Sanctuary (plus a tour, if you stay weekends April-October), and the property is completely vegan, including the complimentary breakfast of delicacies ranging from coconut milk “yogurt” to waffles.
The Thayer Hotel, West Point
You’d expect a hotel that looks like a fortress, is located on the campus of West Point, and has hosted US Presidents and world leaders to be a bit…stodgy. But Thayer is just the opposite: a perfect combination of history and luxury. You can wander for hours through the hallways admiring the US military history-centric art or displays dedicated to distinguished graduates, relax in one of the 151 recently renovated rooms, stroll the immaculate grounds, and end the day gazing at the Hudson River view with a drink in hand at the Zulu Time Rooftop Bar & Lounge.
Old World-Style Inn
Stagecoach Inn, Goshen
The Stagecoach Inn may be one of America’s oldest operating inns (it dates back to 1747, and is older than the village it resides in!) but it feels anything but old. Thanks to new proprietor Faith Ferguson, the former Anthony Dobbins Stagecoach Inn has been restored to its former glory, but with modern amenities, such as flat-screen TVs and high-speed WiFi. The inn, which is within walking distance to the Goshen Historic Track, features five beautifully decorated and spacious rooms named for famous people who’ve stayed there (like Roosevelt and Guggenheim), a library, a solarium, and three separate dining rooms serving gourmet meals.
Wallkill River School of Art, Montgomery
Take note of their slogan, “Unleash Your Inner Artist.” They’re not just a pretty face — the mission of the school and its co-op gallery is to help individuals find their creative bent, and to support artists by providing myriad opportunities to teach, mentor others, and exhibit their work. The school offers fine-art classes, rotating exhibits, the plein-air Art/History Trail, and multiple other beautiful and educational events alike.
Orange County Choppers Café, Newburgh
It’s a motorcycle showroom. No, it’s a burger joint. No, it’s a music venue. But it has a four-lane bowling alley, too. This café defies definition, but — if you couldn’t guess already — it’s a great place to hang with your friends. Good pub-style food (burgers come on OCC-branded brioche buns), drinks, and entertainment ranging from karaoke to popular local bands attract a good following, too.
Spiegeltent at Bard Summerscape, Annandale-On-Hudson
A cross between Cirque du Soleil, sensational live music, and late-night cabaret, the annual Spiegeltent at Bard College offers the ultimate evening of entertainment. Performances take place in a moveable wood and canvas tent — decorated up and down with mirrors and lights of many sizes — where acts wow the crowds from a small stage set literally front and center. This past year saw a lineup featuring Catskill Jazz Factory and the seductive stories of Mx. Justin Vivian Bond, but every summer promises plenty of enchanting mischief.
Powerhouse Theater at Vassar, Poughkeepsie
For six show-stopping weeks every summer, the folks here collaborate with New York Stage & Film to bring fully produced plays, musical workshops, and readings of works-in-progress to the Vassar College campus. An impressive feat, but even more so when you learn many of those shows go on to become Broadway hits (like a certain little one you may have heard of: Hamilton). The theater also runs a unique training program, turning out a number of free events all summer featuring students who have gone on to study at Carnegie Mellon, Juilliard, and Yale.
Howe Caverns, Howes Cave
A trip through the limestone corridors and massive boulders that exist 156 ft below the surface here has become a Hudson Valley rite of passage since the site’s first public exploration in 1842. These days, you can still tour the awesome stalactites while chasing a millennia-old subterranean river, but now the adventure continues above ground, too. Their seasonal Adventure Park features thrills like a high-flying zip line, smile-inducing air jumper, and something they call an H2OGO Ball, a 12-foot inflatable ball filled with five gallons of water that hurtles you 1,100 ft downhill.
USS Slater Destroyer Escort Historical Museum, Albany
Most museums are full of frozen moments from history (artifacts, documents, artworks, etc); this museum is history. The only one of its kind afloat in the country, the nearly 75-year-old USS Slater itself — a Destroyer Escort during WWII and now a National Historical Landmark — serves as a storehouse for wartime memorabilia displayed as it would have been in 1945. Visitors get to see everything from the crew’s shoes stowed under beds to a working radio room and period weaponry as knowledgeable guides tour them between decks and through cabins.
Thomas Cole National Historic Site, Catskill
Remember boring field trips back in the day? Banish that memory. The home of Thomas Cole, the founder of the Hudson River School of landscape painting, has been meticulously restored and features a new immersive multi-media installation. The Main House is furnished in period décor, sure, but wait … that framed letter is actually a projection, and it changes as you watch it. And those paintings on the wall are also projections, with narrations by actor Jamie Bell (Billy Elliot) reciting the artist’s own words, taken from his journals, letters, and essays. A highlight of the restoration is the newly uncovered elaborately painted borders in both parlors (the earliest known, interior decorative painting by the American artist.). The experience absolutely engages you; it’s brought historic preservation, and interest in it, to a whole new level.
Angry Orchard, Walden
Angry Orchard may be a nationally recognized brand, but their Innovation Cider House in Walden offers the ultimate opportunity to branch out — literally. The site features a one-of-a-kind treehouse built by Pete Nelson and the team from Animal Planet’s Treehouse Masters that overlooks the entire estate. Complete with intricate carvings and a swing, the Treehouse doubles as a tasting room where you can sample both regularly available ciders and the latest in orchard-made, experimental styles.
Villa Borghese, Wappingers Falls
If you haven’t visited this special event hall in the last few years, you’ll barely recognize it. Newly added outdoor water walls, sparkling chandeliers in the cocktail lounges, gold-frame Chiavari banquet chairs, granite dance floors, and the theatrical accent lighting are all part of an ambitious ongoing renovation that has made it a top party place of the Hudson Valley.
Bed & Breakfast
Buttermilk Falls Inn & Spa
Walkway over the Hudson
The Wayfinder Experience
The Wayfinder Experience
Emerson Resort & Spa
County Players Falls Theatre
Dance Works Too
Hyde Park Drive-In Theatre
Dutchess County Fair
gen. Montgomery Day
Golf Course (Public)
Apple Green Golf Course
Hudson River Cruise (tie)
Pride of the Hudson
the rip van Winkle
Inn or Hotel (not a chain)
Mohonk Mountain House
Fighting Spirit Karate Studio
Kids’ Birthday Party
Live Music Joint
The Castle Fun Center
Movie Theater (Independent)
Mid-Hudson Children’s Museum
New Windsor Music Academy
Hudson Valley Philharmonic
Place for a Picnic
Mohonk Mountain House
Venue For Plays and Concerts (Indoors)
Venue For Plays and Concerts (Outdoors)
Venue For A Wedding