25 Things Every Hudson Valleyite Must Do in the Region

Check off these Hudson Valley to-dos one weekend at a time.

How many of these Hudson River region activities can you check off your bucket list throughout the year?

The Hudson Valley is home to such a wealth of attractions and to-dos that it is a challenge to know where to begin. Check out our list of must-visit locales for visitors and Valleyites alike, then head over to our “Hudson Valley Bucket List” to plan the staycation of your dreams.

1. Visit the Walkway Over the Hudson

87 Haviland RdHighland; 61 Parker Ave, Poughkeepsie

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After nearly 20 years of planning, fund-raising, legal wrangling — not to mention manual labor — the world’s longest elevated park opened amid much fanfare in October 2009. Since that time, thousands of pedestrians have walked, run, cycled, roller-bladed, or otherwise traversed the one-and-a-quarter-mile span, which links Parker Avenue in Poughkeepsie with the Ulster County village of Highland and connects to the expansive Hudson Valley Rail Trail.

Rising more than 200 feet above the river, the concrete-paved Walkway offers virtually unobstructed views of the Hudson Highlands (Storm King, Mount Taurus) to the south; on a clear day, you can spy the distant Catskills to the north. But a peek over the railing also reveals the swirling river currents, tree-lined shoreline (Highland side), and the rooftops of a number of homes and businesses in Po-town. With parking options on both the Highland and the Poughkeepsie ends of the trail, this clean and well-maintained skyway is sure to thrill even the most jaded Valleyite.

2. Take in a show at the Bardavon

35 Market St, Poughkeepsie

The Bardavon 1869 Opera House — New York State’s oldest continuously operating theater — is Poughkeepsie’s one-stop shop for cultural events of every stripe. A typical season (which runs from September through May) at the 944-seat theater includes concerts by headliners (think Joan Jett, the Indigo Girls, and Natalie Merchant) who are usually booked into much larger venues. But you can also catch performances by established dance and theater companies, watch classic films, experience opera streamed live in HD from the Met, and attend concerts by the Hudson Valley Philharmonic.

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Admiring the ornate decoration in this historic building, however, is almost as exciting as watching the performers. The theater’s original interior was renovated in 1923, turning it from an opera house into a movie palace; the neoclassical/Italian Renaissance design elements from that era — including elaborate plasterwork and a impressive domed ceiling — are still present today. Installed in 1928, the Mighty Wurlitzer pipe organ is the only one in any theater between Manhattan and Albany that remains in its originally intended setting. Saved from the wrecking ball in 1976, the theater was subsequently added to the National Register of Historic Places; it has proven to be an architectural gem as well as a vital arts resource for the Valley — and well worth a visit.

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3. Visit Dia:Beacon

Beekman St, Beacon

In 2003, a 300,000-square-foot former Nabisco box factory on Beacon’s waterfront was converted into this cutting-edge contemporary art museum. Funded in large part by Steve Riggio (chairman of Barnes & Noble Booksellers), the museum is an offshoot of the Dia Foundation, an arts organization with facilities in Manhattan, Utah, and New Mexico — and its presence in the Valley has no doubt fueled the influx of artists who now call the area home. The vast gallery space specializes in exhibiting works that would be difficult (or physically impossible) for smaller museums to accommodate. Permanent installations of works by Andy Warhol, Dan Flavin, Donald Judd, and other contemporary art heavyweights draw the crowds from the city and elsewhere. The museum also offers changing exhibits each season, as well as workshops, lectures, dance performances, tours, and other special events. As a bonus, all Hudson Valley residents receive free admission on the last Sunday of each month.

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4. Ride the Catskill Mountain Railroad

Westbrook Lane Station
55 Plaza Rd, Kingston

Chartered in the early 1980s, the all-volunteer Catskill Mountain Railroad provides rail rides along six miles of track originally laid for the Ulster and Delaware Railroad around the turn of the 20th century. Pulled along by a steam engine, the train chugs past the scenic Esopus Creek and offers close-up — and stupendous — views of the Catskills. A stop at the circa 1900 Phoenicia depot allows passengers to visit the Empire State Railway Museum, which is housed in the building. Look out for the seasonal rides, like the Polar Express, the Rails of Terror, and the Easter Bunny Express, which are guaranteed to delight the little ones.

5. Go apple-picking in the fall

By our count, the 10-county Valley region is home to 80 some-odd apple orchards, most of which welcome visitors to gather apples (and, often, pumpkins too) throughout the fall. Take your pick (pun certainly intended) from among the 14 varieties that are grown locally, including established favorites like the tangy McIntosh, the sweet Macoun, and the all-purpose Cortland or the hybrid Honeycrisp (the tart-but-sweet fruit that is to apples what Twinkies are to snack food).

at the drive ins

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6. See a movie at a drive-in

Things haven’t changed all that much at the Valley’s many drive-in theaters, which is perhaps the best reason to go to one. Relive those hot summer nights of your youth by catching a double feature on a gigantic screen for a fraction of the price you’d pay at the neighborhood multiplex. Technological innovations over the years have resulted in clearer pictures and high quality sound, and the current snack bar offerings go way beyond popcorn and candy. Moviegoers scarf down char-broiled Black Angus burgers at Poughkeepsie’s Overlook Drive-In and fill up on a wide variety of frozen treats at Twist, the ice cream shop at the Jericho Drive-In in Glenmont. You’re still likely to see children perched on car fenders in their pajamas, teenagers canoodling in back seats, and older folks camped out on lawn chairs, just like it was in 1986 — or ’76, or ’66, or even ’56.


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7. Attend the Dutchess County Fair

Dutchess Fairgrounds
6636 Rte 9, Rhinebeck

Close to 500,000 people pass through the turnstiles at the Rhinebeck fairgrounds each year to attend this six-day country extravaganza, which combines traditional fair events (agricultural competitions and the like), performances by top-shelf entertainers, and a midway full of rides, games, and food. First held in 1842, the fair — which is not the oldest in the state (that distinction belongs to Watertown) — is undoubtedly one of the best. Don’t miss top annual attractions, like the talent shows, the SporkRun, and the star-studded performance line-up. And you can’t claim you’ve really done the fair unless you’ve sample the fried dough and the iconic 4-H milkshakes — cholesterol be damned, they’re to die for.


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8. Go shopping at Woodbury Common

498 Red Apple Ct, Central Valley

One of the few malls that requires a map to navigate, this sprawling outdoor complex of 250 factory outlet shops is a bargain-hunter’s dream come true. As a “premium” facility, Woodbury Common includes dozens of high-end retailers you won’t find at other discount malls; whether it’s a pair of Tory Burch flats, new Nike kicks, or a Celine bag, you’ll find it here (along with Polo Ralph Lauren blazers, Michael Kors backpacks, Burberry trenches, and just about anything else your heart desires). A popular destination for overseas travelers, who arrive from Manhattan by the busload, the site welcomes new stores each year. Snag coupons and vouchers for additional savings by registering online for VIP Shopper Club membership. There’s no sign-up cost, and the perks are well worth the effort.

9. Ride the simulator at the Harness Racing Museum

240 Main St, Goshen

Orange County is the home of U.S. harness racing. Goshen’s Historic Track — a National Historic Landmark — was established in 1838, and races are still held there each summer. Although he competed on the track only once, Hambletonian 10 — born in Sugar Loaf in 1849 — sired over 1,000 foals during his 24 years at stud. It’s said that just about all of today’s Thoroughbreds come from his line. The town’s Harness Racing Museum is adjacent to the track, and provides visitors with a complete history of this exciting sport — including a 3D simulation of an actual race. Your seat jostles and tilts as your “horse” (pictured on a video screen) jockeys its way to the front of the pack — kicking up dust and losing a shoe in the process.

10. Take a leaf-peeping drive

It’s hard to deny that autumn is the most beautiful season in the Valley (to us, at least). Once the maples, oaks, birches, hemlocks, and other leafy denizens change into their fall clothes, snub your nose at the current price of gas and head for the highway to watch their annual fashion show. While the Taconic Parkway is a favorite route, any tree-laden country lane should do the trick. To see the most colorful display, plan to take your jaunt after a succession of warm, sunny days that are followed by cool (but not freezing) nights.

11. Swim in Lake Taghkanic

1528 Route 82, Ancram

Our Valley offers dozens of places to “play outside” — hiking trails, bike paths, and the like. With no oceanfront within about 50 miles, however, we’re a little short on beach swimming. That’s one of the reasons why taking a dip at Lake Taghkanic State Park is so much fun. The 156-acre lake has not one, but two sandy beaches — which are usually filled to capacity once the thermometer hits 90 degrees. Not into sunbathing? The park also offers camping facilities; rowboat, paddleboat, and kayak rentals; sports fields and playgrounds; and picnic areas. With an entrance located right on the Taconic Parkway, getting there is a breeze.

Tis the season 🌽ðŸ…🌽ðŸ…

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12. Visit a local farm

For centuries, residents have been tilling the soil in our fertile Valley. From the Black Dirt onion fields in Orange County to the cattle herds in Dutchess and the fruit orchards in Columbia, these picturesque (and often family-run) businesses are everywhere — and they are in trouble. Large-scale agricultural production has been putting the squeeze on smaller farmers for years. Yet the burgeoning interest in agricultural alternatives — think “slow” food, farm-to-table initiatives, and organic farming — is giving many local farmers a new focus. Say thanks to our local providers by visiting a farm and, better still, by chowing down on an ear of butter-and-sugar corn or a just-picked beefsteak tomato from a local farmstand.

13. Do something (other than ski) at Hunter Mountain

64 Klein Ave, Hunter

Sure, we already know that Hunter — with its 58 trails, top-notch snowmaking equipment, and great après-ski amenities — is one of the best places in the Northeast to hit the slopes. What you may not know is that the mountain offers family fun programming during the other three seasons of the year as well. Check out the Scenic Skyride or the Zipline Canopy Tour for a thrilling views that rival any drone shot. When the snow’s not flying, the site plays host to some of the region’s most anticipated festivals, from TAP New York to Taste of Country and Octoberfest.

14. Visit Olana

5720 State Route 9G, Hudson

Historic houses — while not exactly a dime a dozen — are certainly not difficult to come by here in the Valley. Yet Olana, Frederic Edwin Church’s Persian-style home in Hudson, is more than a tad different from those familiar Beaux Arts mansions and 18th-century Dutch stone structures. Church — a prominent member of the Hudson River School of painters — designed the building himself after a family trip to the Middle East in the late 1860s. With its turrets, arches, and stenciled decoration, the home took more than 20 years to build and cost Church $90,000, a veritable fortune in those days. Both a state and national historic site, the house is situated atop a high hill that offers spectacular views of the Hudson and Catskills. Book a tour in advance to explore the interior of the colorful estate or stop by for an impromptu visit to explore the 250-acre grounds.

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15. Follow the Hudson River School Art Trail

The Hudson River School was America’s first homegrown art movement. Thomas Cole, Frederic Church, Jasper Cropsey, and other 19th-century painters depicted dramatic views of the Hudson and Catskills in their works, and inadvertently helped our fledgling country establish its unique identity. The Hudson River School Art Trail identifies 20 spots — including Olana, North-South Lake, and Kaaterskill Falls — where the surrounding landscape has been forever immortalized on canvas by one or more of these artist icons. Choose a crisp autumn afternoon, follow the trail from beginning to end, and combine a cultural adventure with some world-class leaf-peeping.

16. Take a boat ride on the Hudson

Getting a mid-river view of the Valley’s legendary landscape is a not-to-be-missed experience — and there are several ways to do it (even if you don’t own a cabin cruiser). Book a spot on one of the cruisers which regularly ply the waters between Haverstraw and Hudson. The on-board tour guides provide a bit of history and folklore as you motor past West Point, Bannerman Castle, the Great Estates area, and similar sites. During the summer months, the Beacon Sloop Club’s flagship Woody Guthrie sets sail each weeknight, offering free rides and a little river education. Sails on the sloop Clearwater can also be arranged.

I may be over the snow, but it sure makes for a pretty picture.

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17. Taste Tuthilltown Whiskey

14 Grist Mill Lane, Gardiner

For more than two centuries, the Tuthilltown Gristmill in Gardiner — a National Historic Site — used water from a nearby creek to turn local grains into flour. In 2003, Ralph Erenzo purchased the mill, and — along with partner Brian Lee — proceeded to convert one of its granaries into a distillery. The result: the first (legal) production of hard liquor in New York State since Prohibition. The partners now turn out small batches of vodka, whiskey, rum, and other spirits using grains and fruits grown on nearby farms. Especially noteworthy is their Hudson Baby Bourbon. Made from New York-grown corn, it is beloved for its smooth, caramel-and-vanilla-tinged taste.

18. Explore Uptown Kingston

Known to Kingstonians as the Stockade District, this eight-block section of the city — first settled by the Dutch in 1658 — is crammed full of historic buildings. A few highlights: the Senate House (built in 1676), where the senators of the newly formed State of New York held their first meeting in 1777; the Minard Lafever-designed Old Dutch Church (1852), a National Historic Landmark; and the junction of Crown and John streets, the only intersection in the country that has an early Dutch stone house on each of its four corners. The Friends of Historic Kingston offer guided walking tours of the district on the first Saturday of every month from May through October.

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19. Take a spin on the Bear Mountain Merry-Go-Round

Palisades Parkway, Bear Mountain

The kids will have a grand time riding this colorful carousel — and adults will appreciate its beauty and Valley-centric focus. After a lack of funds scuttled plans to build a merry-go-round at Bear Mountain State Park not once, but twice (in 1916 and again in the 1930s), the ride finally debuted in 2007. Housed in an 8,000-square-foot stone and timber pavilion (which includes a fireplace and catering space for small events), the carousel is now one of the site’s main attractions. Rather than the usual horses, the 42 hand-carved and painted seats on the whirligig represent animals native to the Hudson Valley: bears, bobcats, swans, river otters, eagles, foxes, geese, etc. The rounding boards illustrate the park’s early history, with hand-painted scenes of the Hudson River, Perkin’s Tower, and the Bear Mountain Inn. The recorded music comes from a 1926 Wurlitzer Pipe Band Organ.

20. Stroll through Storm King Art Center

1 Museum Rd, New Windsor

One of the brightest jewels in the Valley’s cultural crown, this Orange County sculpture park showcases more than 100 carefully sited sculptures across the 500 acres of hills, fields, and woodlands. Created between 1945 and the present day, the sculptures are often monumental in size (you have probably caught sight of Mark di Suvero’s orange-painted Mother Peace while traveling on the Thruway south of Newburgh) and are representative of each artist’s oeuvre. You’ll see a mile-long stone wall by Andy Goldsworthy; one of Alexander Calder’s last stabiles; and Maya Lin’s Storm King Wavefield, an 11-acre environmental work composed of grass and earth. With a rotating line-up of exhibitions and education programs, there is always something new to see at Storm King. Pro tip: Slip on comfortable shoes before you leave the house. Although trams are available to help you get around the park, walking up to, around, and even through the sculptures is part of the fun.

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21. Bike along the Putnam County Trailway

Making adaptive reuse of the abandoned Putnam Division of the New York Central Railroad, this paved pathway is an ideal locale for bikers, runners, and walkers. The 12 miles wind their way from the Westchester/Putnam border through Mahopac and Carmel and into the Harlem Line Tracks. Most of the trail is fairly flat and scenic, with densely wooded sections and views of Lake Gleneida and the Middle Branch Reservoir (which it crosses). A go-to spot for families, the trail is also perfect for cyclists looking to get a good day’s workout. The southern end connects to Westchester’s North County Trailway, which runs from north to south for 22 miles and connects to other routes leading all the way into the Bronx.

22. Have brunch at the Thayer

674 Thayer Rd, West Point
845.446.4731, ext. 7929

Listed on the National Registry of Historic Places, West Point’s Thayer Hotel — built in 1926 — has played host to multi-star generals from Douglas MacArthur to Dwight Eisenhower (who visited during his presidential term). The hoi polloi can get a taste of its history on Sundays by indulging in the legendary Champagne Brunch. This midday meal at MacArthur’s Riverview Restaurant features a groaning board of dishes that are a far cry from military mess-hall grub: savory smoked salmon, dreamy Bananas Foster, and unlimited glasses of champagne, mimosas, and Bloody Marys. Pair the cuisine with the jaw-dropping views of the Hudson visible out the dining room windows, and we dare you to find a more relaxing way to spend a Sunday.

23. Sample wine at a Valley vineyard

The oldest wine-making region in the country, the Valley is home to some of the nation’s top wine producers — and the quality of their vintages rivals what’s produced on Long Island and in the Finger Lakes. From “traditional” wines like Chardonnay (Millbrook Vineyards) and Cabernet (Benmarl Winery) to fruit liqueurs and hard ciders (Warwick Valley Winery) and dessert offerings (Strawberry wine from Baldwin Vineyards), there’s a wine to suit every palate. Looking for something new? Try Clinton Vineyards‘ Cassis, a black currant wine, or the Candy Ass Red from Glorie Farm Winery, which is made with Concord grapes.

Rocks were climbed and sunburn was got #mohonkpreserve

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24. Hike through the Lemon Squeeze

Okay, some of you — the claustrophobic, those with a fear of heights, and anyone with common sense — might want to take a pass on this one. But for the truly intrepid, following the Mohonk Preserve’s strenuous Labyrinth Trail through the famed Lemon Squeeze section is an exhilarating experience that you can only find here in the Valley. Part of the Appalachian Trail, the Labyrinth follows the base of the Shawangunk cliffs, eventually climbing its way up to Ephraim’s Point (a table rock where 19th-century hunter Ephraim Decker wrestled a deer by the horns with his bare hands — or so the legend goes). To reach the point, though, you’ve first got to negotiate “the crevice” — a six-to-eight-foot-wide space that runs vertically between two gigantic quartz rocks. While that’s rough as it is, the Crevice narrows even further — to just one to two feet wide — so you’re in the Lemon Squeeze itself. Hikers make their way up sideways using “ladders” made from tree branches. The effort is worth it, however, when you finally reach Skytop, the ridge summit that offers unobstructed views of the Hudson, the Catskills, and beyond.

25. Attend the Woodstock Film Festival

13 Rock City Rd, Woodstock

Located in the heart of music history, Woodstock Film Festival has a national reputation for high quality independent films created by industry neophytes and veterans alike . Dozens of films — a number of which zero in on controversial subjects — are screened during the five-day event, which also includes panel discussions, special awards ceremonies, and, of course, legendary parties. With its close proximity to Manhattan, the festival attracts more than its fair share of cinematic bigwigs, who can often be spotted browsing the shops along Tinker Street.

Related: 50 Reasons to Love Summer in the Hudson Valley

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