The Best Fun & Leisure Activities in the Hudson Valley

Hudson River Skywalk
Photo by Beth Schneck Photography

Editors’ Picks

– Curated Day Trip Company –

Go Love NY

Westchester residents Robin Helman and Elizabeth Knell launched Go Love NY in fall 2019 to curate private and small-group Hudson Valley excursions, with a focus on food, nature, and culture. The offerings change, but expect experiences like kayaking to Bannerman Castle, a private tour and happy hour at Russel Wright’s Manitoga House in Garrison, visits to local alpaca or dairy farms, and tours of Stonecrop Gardens and flower arranging workshops with The Parcel Flower Co.

Photo courtesy of Go Love NY

– Fall Festival –

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Warwick’s Applefest

More than 30,000 visitors attend this annual event each October (canceled for 2020 due to COVID-19), celebrating one of the Hudson Valley’s finest agricultural products. Started as a harvest celebration more than 30 years ago, Applefest has turned into one of our region’s favorite events, featuring a variety of food, hundreds of craft vendors, activities for children, a farmers’ market, music, pie eating and baking contests, and more.

– History Tours –

Hudson Virtual Tours

When COVID-19 kept us homebound for months, we turned to Hudson Virtual Tours for online peeks inside historic sites across the Valley. With offices in Troy and Woodstock, the video tour company offers free inside looks everywhere from Albany’s Van Ostrande-Randliff House to Oakwood Cemetery in Troy.
Troy, Woodstock;

– Mother’s Day Outing –

Tulip Festival

The Albany Tulip Festival, always slated for the weekend of Mother’s Day, is a delightful way to take in the season’s blooms. This year, even the pandemic couldn’t stop the 140,000 tulips in 150 varieties from making their debut. The festival — which normally includes concerts, a street scrubbing event, and a Tulip Queen coronation and procession — went virtual, with photo and video updates, online performances, and self-guided tours.

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Photo courtesy of Discover Albany

– Nature Center for Kids –

Forsyth Nature Center

Connecting with the outdoors is one of the great things about our region. At Kingston’s Forsyth Nature Center, nature is captured in a bite-sized educational environment perfect for kids and teenagers. The center offers more than two dozen animal exhibits, as well as beautiful gardens ideal for roaming and taking pictures.

– New Pedestrian Path (South) –

The Path on the Gov. Mario M. Cuomo Bridge

The building of a new bridge across one of the widest spans of the Hudson River was a long time coming, but it was well worth the wait, especially for walkers and cyclists. The 3.6-mile path has a 12-foot wide shared pedestrian/cyclist lane, six scenic resting spots, and is home to the largest permanent public art installation in the New York metro area. Bonus: the path connects two of the Valley’s best Rivertowns and has food trucks on both ends of the path.
Nyack, Tarrytown;

Photo courtesy of the New York State Bridge Authority

– New Pedestrian Path (North) –

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Hudson River Skywalk

Landscape artist Thomas Cole, the founder of the Hudson River School, and his student, Frederic Church, now have a modern-day connection: a three-mile walkway on the Rip Van Winkle Bridge that connects their homes in Catskill and Hudson, respectively. We can’t think of a better way to appreciate the landscapes that the artists brought to life than taking it in on foot.
Catskill, Hudson;

– Night Out for the Whole Family –

Factoria at Charles Point

Enjoy a date with your spouse at Fin & Brew, one of Westchester’s best river-view restaurants, while your kids dine and dash downstairs to Spins Hudson, the largest entertainment venue on the Hudson. Or, meet up with friends for more casual fare and some fine brews at River Outpost Brewing Co., conveniently located between Spins’ arcade games and the indoor climbing and laser tag quarters.

– Nostalgic Day Trip –

The Den of Marbletown

Did you know there’s a teddy bear museum in the Hudson Valley? On the outskirts of Kingston, The Den of Marbletown is home to more than 5,000 collectible bears and dolls. After a tour to bring out your inner child, head to Papa Bear’s Kitchen for seasonal salads, sandwiches, and 40-plus varieties of bubble tea.
Kingston; find them on Facebook

– Old-Fashioned Family Fun –

Four Brothers Drive-In

When the Stephanopoulos family opened their drive-in in 2013, they built the bones of a drive-in (parking lot, large screen, snack shop), but with modern twists like locally sourced food and overnight facilities (camping and Hotel Carvana, a cool camper for rent). After a long spring of quarantine, the theater’s May re-opening was godsend to Hudson Valleyites, hosting double-feature movies, as well as high school graduations, live music, and new releases (Liam Neeson and his son stopped by to screen and discuss their new film).

Photo by John Halpern

– Place to Get a Ski Season Pass –

Hunter Mountain

More than just a local favorite, Hunter Mountain is the only New York ski spot on the Epic Pass — a coveted, year-round ski pass that offers unlimited riding at 37 mountains worldwide. Skiers and snowboarders nationwide visit the mountain every year to spend the day exploring the 67 trails and enjoy après-ski at one of the 12 on-site dining options.

– Skills-Building Classes for Toddlers –

The Little Gym of Kingston

As the name implies, this gym is all about the little ones. Instructors make sure that your tots learn muscle control, coordination, and skill development alongside color recognition, independence, and sharing from an early age through their three-dimensional learning approach. Classes are split into Birds, Beasts, and Super Beasts, and also sharpen interpersonal skills and brain power.

– Unexpected 180 –

The Old Game Farm and Long Neck Inn

After a tumultuous history in the Hudson Valley, the Catskill Game Farm was reborn as The Old Game Farm, a mixed-use retreat for camping, self-guided tours, and overnights at The Long Neck Inn. For Hudson Valleyites who remember day trips to the Catskill zoo, each visit is a walk down memory lane.

– Way to Let Off Steam –

Hudson Valley Hatchet

Is there a better way to release your anger and frustration than throwing an axe at a target? We think not. Hudson Valley Hatchet creates pop-ups (check the website to find out where to catch them next) and private events, providing all the equipment needed to get out your pent-up feelings safely.

Photo courtesy of Hudson Valley Hatchet

– Winter Holiday Event (South) –

Westchester’s Winter Wonderland

Benefiting Westchester Parks Foundation, this month-long holiday attraction is sure to be your family’s next holiday tradition (if it isn’t already). Visit with Santa and friends, attend a circus under a heated big top tent, enjoy amusement rides, take a spin on the outdoor ice rink (skates included!), and be dazzled by the holiday light show. All-inclusive tickets are valid for any day of the season and admission is free for children under 3. (At press time, this year’s event was not confirmed.)
Valhalla; find them on Facebook

– Winter Holiday Event (North) –

Winter Walk

For one evening each December, downtown Hudson transforms for its Winter Walk with festive storefront displays, horse-drawn carriages, stilt-walkers, carolers, Christmas characters, and music coming from every which way. The event ceremoniously begins with the Santa Parade and procession to Hudson Hall. There are kid-friendly activities, so rally the whole family to be ready for a holiday to remember. (At press time, this year’s event was not confirmed.)


– Hidden Gem Castle –

Wing’s Castle

If ever there was a place for Rapunzel to call home in the Hudson Valley, Wing’s Castle would be it. The lifetime work of artist Peter Wing, the castle now serves as a family home and B&B. A true fairytale residence, it comes with its own dungeon and moat, with nary a dragon in sight.

– Hotel With a Waterfall View (East of Hudson River) –

The Roundhouse

If you’re spending the night at The Roundhouse, spring for a room with a view of Overlook Falls. Many elements of the original 200-plus-year-old building remain, including the oversized factory windows, wooden beams, and bricks. Staying or not, don’t skip dining at the on-site restaurant or a fireside drink at the bar — both have views of the falls.

Photo by Teresa Horgan

– Hotel With a Waterfall View (West of Hudson River) –

Diamond Mills Hotel & Tavern

Each of the 30 guest rooms at this boutique hotel has a balcony that overlooks the Esopus Creek, which powered the Martin Cantine Paper Mill that stood on this site from 1888 to 1975. After a fire destroyed the building and left the lot vacant for three decades, entrepreneur Tom Struzzieri opened Diamond Mills in 2011, quickly garnering awards. If that’s not enough, there’s also The Tavern restaurant, which sources local ingredients for al fresco dining with (you guessed it) gorgeous waterfall views.

– Nature-Centric Pampering –

Emerson Resort & Spa

Everything about this luxury resort — named after Ralph Waldo Emerson — is focused on ways to enjoy the beauty of its Catskill Mountains’ surroundings. Whether it’s taking one of their many nature walks, biking on the nearby Ashokan Rail Trail, eating a locally sourced meal at Woodnotes Grille or receiving a luxurious treatment — inspired by the earth’s elements — at their 6,193-sq-ft spa, you’ll be sure to leave feeling refreshed and connected with nature.
Mount Tremper;

Readers’ Picks

– Bike/Rail Trail –

Walkway Over the Hudson


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– Bowling Alley –

Spins Bowl

Carmel, Hyde Park, Poughkeepsie, Wappingers Falls

– Drive-In Theater –

Hyde Park Drive In

Hyde Park

– Fair –

Dutchess County Fair



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– Festival –

Brewster Fall Festival


– Girls’ Night Out –

Moonlight Café & Caterers


– Golf Course (Public) –

Apple Greens Golf Course



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– Hudson River Cruise –

Hudson River Cruises


– Kayak or Paddleboard Rental –

The River Connection

Hyde Park

– Park –

Town of Greenport Park

Find them on Facebook

– Place for a Picnic –

Vanderbilt Mansion National Historic Site

Hyde Park

– Pro or Semi-Pro Sports Team –

Hudson Valley Renegades

Wappingers Falls


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– Ski Area –

Windham Mountain


– Trivia Night –

Spotty Dog Books & Ale



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– U-pick Farm –

DuBois Farms


– Bed & Breakfast or Inn (Not a Chain) –

Batterby House


– Hotel or Resort (Not a Chain) –

Rocking Horse Ranch Resort


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